TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7229
AB  - Computational investigation at the BHandHLYP/6-311+G(d,p) level of theory of the gas-phase tautomerism of 2- and 4-pyridones confirmed the slight prevalence of lactim in the case of the former, but its dominance in the case of the latter, as shown previously. Examination of aromaticity by using HOMA, EDDB, NBOdel, NICS and AICD led to the conclusion that tautomerization of 4-pyridone results in greater aromaticity gain. It is also driven by the Pauli repulsion relief, which was revealed by the tautomerization energy decomposition analysis. By contrast, in the case of 2-pyridone, lactim is favoured by orbital and electrostatic interactions and disfavoured by the Pauli repulsion. Aromaticity gain in this case is smaller. The position of the tautomeric equilibrium can be modulated by substituent inductive effects (Cl and F), inductive and resonance effects (NH2 and NO2), hydrogen bonding (NO2), and medium polarity, the increase of which increases lactam population.
PB  - Royal Society of Chemistry (RSC)
T2  - Organic & Biomolecular Chemistry
T1  - Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects
VL  - 22
IS  - 1
SP  - 144
EP  - 158
DO  - 10.1039/D3OB01588B
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan",
year = "2023",
abstract = "Computational investigation at the BHandHLYP/6-311+G(d,p) level of theory of the gas-phase tautomerism of 2- and 4-pyridones confirmed the slight prevalence of lactim in the case of the former, but its dominance in the case of the latter, as shown previously. Examination of aromaticity by using HOMA, EDDB, NBOdel, NICS and AICD led to the conclusion that tautomerization of 4-pyridone results in greater aromaticity gain. It is also driven by the Pauli repulsion relief, which was revealed by the tautomerization energy decomposition analysis. By contrast, in the case of 2-pyridone, lactim is favoured by orbital and electrostatic interactions and disfavoured by the Pauli repulsion. Aromaticity gain in this case is smaller. The position of the tautomeric equilibrium can be modulated by substituent inductive effects (Cl and F), inductive and resonance effects (NH2 and NO2), hydrogen bonding (NO2), and medium polarity, the increase of which increases lactam population.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Organic & Biomolecular Chemistry",
title = "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects",
volume = "22",
number = "1",
pages = "144-158",
doi = "10.1039/D3OB01588B"
}

Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M.. (2023). Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry
Royal Society of Chemistry (RSC)., 22(1), 144-158.
https://doi.org/10.1039/D3OB01588B

Baranac-Stojanović M, Aleksić J, Stojanović M. Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry. 2023;22(1):144-158.
doi:10.1039/D3OB01588B .

Baranac-Stojanović, Marija, Aleksić, Jovana, Stojanović, Milovan, "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects" in Organic & Biomolecular Chemistry, 22, no. 1 (2023):144-158,
https://doi.org/10.1039/D3OB01588B . .

TY  - JOUR
AU  - Smiljanić, Katarina
AU  - Prodić, Ivana
AU  - Trifunović, Sara
AU  - Krstić-Ristivojević, Maja
AU  - Aćimović, Milica G.
AU  - Stanković Jeremić, Jovana
AU  - Lončar, Biljana
AU  - Tešević, Vele
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7198
AB  - As byproducts of essential oil distillation, hydrolates are used in natural cosmetics/biomedicine due to their beneficial skin effects. However, data on their safety with relevant biological targets, such as human skin cells, are scarce. Therefore, we have tested nine hydrolates from the Lamiaceae family with skin fibroblasts that are responsible for extracellular collagenous matrix builds. Thyme, oregano, and winter savoury hydrolates showed several times higher total phenolics, which correlated strongly with their radical scavenging and antioxidative capacity; there was no correlation between their viability profiles and the reducing sugar levels. No proteins/peptides were detected. All hydrolates appeared safe for prolonged skin exposure except for 10-fold diluted lavender, which showed cytotoxicity (~20%), as well as rosemary and lavandin (~10%) using viability, DNA synthesis, and cell count testing. Clary sage, oregano, lemon balm, and thyme hydrolates (10-fold diluted) increased fibroblast viability and/or proliferation by 10–30% compared with the control, while their viability remained unaffected by Mentha and winter savoury. In line with the STITCH database, increased viability could be attributed to thymol presence in oregano and thyme hydrolates in lemon balm, which is most likely attributable to neral and geranial. The proliferative effect of clary sage could be supported by alpha-terpineol, not linalool. The major volatile organic compounds (VOCs) associated with cytotoxic effects on fibroblasts were borneol, 1,8-cineole, and terpinene-4-ol. Further research with pure compounds is warranted to confirm the roles of VOCs in the observed effects that are relevant to cosmetic and wound healing aspects.
PB  - MDPI
T2  - Antioxidants
T1  - Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts
VL  - 12
IS  - 11
DO  - 10.3390/antiox12111988
ER  - 

@article{
author = "Smiljanić, Katarina and Prodić, Ivana and Trifunović, Sara and Krstić-Ristivojević, Maja and Aćimović, Milica G. and Stanković Jeremić, Jovana and Lončar, Biljana and Tešević, Vele",
year = "2023",
abstract = "As byproducts of essential oil distillation, hydrolates are used in natural cosmetics/biomedicine due to their beneficial skin effects. However, data on their safety with relevant biological targets, such as human skin cells, are scarce. Therefore, we have tested nine hydrolates from the Lamiaceae family with skin fibroblasts that are responsible for extracellular collagenous matrix builds. Thyme, oregano, and winter savoury hydrolates showed several times higher total phenolics, which correlated strongly with their radical scavenging and antioxidative capacity; there was no correlation between their viability profiles and the reducing sugar levels. No proteins/peptides were detected. All hydrolates appeared safe for prolonged skin exposure except for 10-fold diluted lavender, which showed cytotoxicity (~20%), as well as rosemary and lavandin (~10%) using viability, DNA synthesis, and cell count testing. Clary sage, oregano, lemon balm, and thyme hydrolates (10-fold diluted) increased fibroblast viability and/or proliferation by 10–30% compared with the control, while their viability remained unaffected by Mentha and winter savoury. In line with the STITCH database, increased viability could be attributed to thymol presence in oregano and thyme hydrolates in lemon balm, which is most likely attributable to neral and geranial. The proliferative effect of clary sage could be supported by alpha-terpineol, not linalool. The major volatile organic compounds (VOCs) associated with cytotoxic effects on fibroblasts were borneol, 1,8-cineole, and terpinene-4-ol. Further research with pure compounds is warranted to confirm the roles of VOCs in the observed effects that are relevant to cosmetic and wound healing aspects.",
publisher = "MDPI",
journal = "Antioxidants",
title = "Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts",
volume = "12",
number = "11",
doi = "10.3390/antiox12111988"
}

Smiljanić, K., Prodić, I., Trifunović, S., Krstić-Ristivojević, M., Aćimović, M. G., Stanković Jeremić, J., Lončar, B.,& Tešević, V.. (2023). Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts. in Antioxidants
MDPI., 12(11).
https://doi.org/10.3390/antiox12111988

Smiljanić K, Prodić I, Trifunović S, Krstić-Ristivojević M, Aćimović MG, Stanković Jeremić J, Lončar B, Tešević V. Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts. in Antioxidants. 2023;12(11).
doi:10.3390/antiox12111988 .

Smiljanić, Katarina, Prodić, Ivana, Trifunović, Sara, Krstić-Ristivojević, Maja, Aćimović, Milica G., Stanković Jeremić, Jovana, Lončar, Biljana, Tešević, Vele, "Multistep Approach Points to Compounds Responsible for the Biological Activity and Safety of Hydrolates from Nine Lamiaceae Medicinal Plants on Human Skin Fibroblasts" in Antioxidants, 12, no. 11 (2023),
https://doi.org/10.3390/antiox12111988 . .

TY  - JOUR
AU  - Paunović, Dusanka
AU  - Mirković, Milica
AU  - Mirković, Nemanja
AU  - Tešević, Vele
AU  - Stanković Jeremić, Jovana
AU  - Todosijević, Marina
AU  - Radulović, Zorica
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7226
AB  - The use of truffles in food is based mainly on the addition of artificial flavors, aiming to achieve an intense aroma in the products. As truffle is a natural product with nutritional and functional properties, it is important to find an optimal method for truffle storage. As the microbiota contribute to truffle aroma, the bacterial and yeast compositions in the rhizosphere and fruiting body of the truffle and the impact of different freezing methods on the volatile profile of the truffle Tuber aestivum during 90 days of the storage were determined. Bacteria and yeasts isolates were identified using 16s rRNA and 18s rRNA. The effect of freezing truffles at -20°C and -80°C with and without previous dipping in liquid N2 on the volatile compounds was observed using GC/MS. The results demonstrated that the isolated bacteria belonged to the phylum Proteobacteria, Firmicutes and Actinobacteria, and the identified species mainly belonged to Firmicutes, genus Bacillus sp. Isolated yeasts were identified as Cryptococcus sp., Debaromyces hanseinii, Candida fermentati and Rhodotorula mucilaginosa. The GC/MS analysis revealed that frozen truffle samples were richer in the compounds 2-butanone, 2-methyl-butanal, methanethiol and 2-butanol after freezing or during storage. The content of DMS, acetaldehyde, 3-octanone, ethanol, and 2-methyl-1-propanol significantly decreased immediately after freezing. Overall, the gained results indicated that freezing of truffles as a preservation method had profound effects on the volatile compounds, while previous dipping in liquid N2 showed no significant impact on the volatile profile of truffle Tuber aestivum.
AB  - Primena tartufa u hrani se uglavnom zasniva na dodavanju veštačkih aroma, sa  ciljem postizanja intenzivne arome tartufa u proizvodima. S obzirom na to da su  tartufi proizvodi sa nutritivnim i funkcionalnim karakteristikama, važno je pronaći  optimalan način za skladištenje tartufa. Pošto mikrobiota doprinosi aromi tartufa,  sastav bakterija i kvasaca u rizosferi i plodonosnom telu srpskog tartufa, kao i uticaj  različitih metoda smrzavanja na isparljiva jedinjenja tartufa Tuber aestivum ispitivan  je tokom 90 dana skladištenja. Bakterije i kvasci su izolovani iz svežeg tartufa i  izolati su identifikovani korišćenjem 16s rRNK i 18s rRNK. Uticaj smrzavanja  tartufa na -20°C i -80°C sa i bez prethodnog potapanja u tečni N2 na sadržaj  isparljivih jedinjenja ispitivan je korišćenjem GC/MS. Rezultati ispitivanja su  pokazali da izolovane bakterije pripadaju carstvu Proteobacteria, Firmicutes i  Actinobacteria, pri čemu identifikovane vrste uglavnom pripadaju Firmicutes, rod  Bacillus sp. Izolovani kvasci su identifikovani kao Cryptococcus sp., Debaromyces  hanseinii, Candida fermentati i Rhodotorula mucilaginosa. Analiza GC/MS je  ukazala na razlike u profilu isparljivih jedinjenja svežeg i smrznutog tartufa.  Smrznuti uzorci su više sadržali komponente kao što su 2-butanon, 2-metil-butanal,  metanetiol i 2-butanol nakon smrzavanja ili tokom skladištenja. Sadržaj DMS,  acetaldehida, 3-octanona, etanola, 2-metil-1-propanola značajno se smanjio odmah  nakon smrzavanja. Dobijeni rezultati ukazuju da smrzavanje tartufa kao metoda  konzervacije ima značajan uticaj na isparljiva jedinjenja, pri čemu potapanje u tečni  N2 nije pokazalo značajan uticaj na isparljiva jedinjenja tartufa Tuber aestivum.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of Agricultural Sciences, Belgrade
T1  - Serbian black truffle Tuber aestivum: Microbiota and effects of different freezing regimes on volatile aroma compounds during storage
T1  - Srpski crni tartuf tuber aestivum: mikrobiota I uticaj različitih režima smrzavanja na isparljiiva aromatična jedinjenja tokom skladištenja
VL  - 68
IS  - 3
SP  - 329
EP  - 346
DO  - 10.2298/JAS2303329P
ER  - 

@article{
author = "Paunović, Dusanka and Mirković, Milica and Mirković, Nemanja and Tešević, Vele and Stanković Jeremić, Jovana and Todosijević, Marina and Radulović, Zorica",
year = "2023",
abstract = "The use of truffles in food is based mainly on the addition of artificial flavors, aiming to achieve an intense aroma in the products. As truffle is a natural product with nutritional and functional properties, it is important to find an optimal method for truffle storage. As the microbiota contribute to truffle aroma, the bacterial and yeast compositions in the rhizosphere and fruiting body of the truffle and the impact of different freezing methods on the volatile profile of the truffle Tuber aestivum during 90 days of the storage were determined. Bacteria and yeasts isolates were identified using 16s rRNA and 18s rRNA. The effect of freezing truffles at -20°C and -80°C with and without previous dipping in liquid N2 on the volatile compounds was observed using GC/MS. The results demonstrated that the isolated bacteria belonged to the phylum Proteobacteria, Firmicutes and Actinobacteria, and the identified species mainly belonged to Firmicutes, genus Bacillus sp. Isolated yeasts were identified as Cryptococcus sp., Debaromyces hanseinii, Candida fermentati and Rhodotorula mucilaginosa. The GC/MS analysis revealed that frozen truffle samples were richer in the compounds 2-butanone, 2-methyl-butanal, methanethiol and 2-butanol after freezing or during storage. The content of DMS, acetaldehyde, 3-octanone, ethanol, and 2-methyl-1-propanol significantly decreased immediately after freezing. Overall, the gained results indicated that freezing of truffles as a preservation method had profound effects on the volatile compounds, while previous dipping in liquid N2 showed no significant impact on the volatile profile of truffle Tuber aestivum., Primena tartufa u hrani se uglavnom zasniva na dodavanju veštačkih aroma, sa  ciljem postizanja intenzivne arome tartufa u proizvodima. S obzirom na to da su  tartufi proizvodi sa nutritivnim i funkcionalnim karakteristikama, važno je pronaći  optimalan način za skladištenje tartufa. Pošto mikrobiota doprinosi aromi tartufa,  sastav bakterija i kvasaca u rizosferi i plodonosnom telu srpskog tartufa, kao i uticaj  različitih metoda smrzavanja na isparljiva jedinjenja tartufa Tuber aestivum ispitivan  je tokom 90 dana skladištenja. Bakterije i kvasci su izolovani iz svežeg tartufa i  izolati su identifikovani korišćenjem 16s rRNK i 18s rRNK. Uticaj smrzavanja  tartufa na -20°C i -80°C sa i bez prethodnog potapanja u tečni N2 na sadržaj  isparljivih jedinjenja ispitivan je korišćenjem GC/MS. Rezultati ispitivanja su  pokazali da izolovane bakterije pripadaju carstvu Proteobacteria, Firmicutes i  Actinobacteria, pri čemu identifikovane vrste uglavnom pripadaju Firmicutes, rod  Bacillus sp. Izolovani kvasci su identifikovani kao Cryptococcus sp., Debaromyces  hanseinii, Candida fermentati i Rhodotorula mucilaginosa. Analiza GC/MS je  ukazala na razlike u profilu isparljivih jedinjenja svežeg i smrznutog tartufa.  Smrznuti uzorci su više sadržali komponente kao što su 2-butanon, 2-metil-butanal,  metanetiol i 2-butanol nakon smrzavanja ili tokom skladištenja. Sadržaj DMS,  acetaldehida, 3-octanona, etanola, 2-metil-1-propanola značajno se smanjio odmah  nakon smrzavanja. Dobijeni rezultati ukazuju da smrzavanje tartufa kao metoda  konzervacije ima značajan uticaj na isparljiva jedinjenja, pri čemu potapanje u tečni  N2 nije pokazalo značajan uticaj na isparljiva jedinjenja tartufa Tuber aestivum.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of Agricultural Sciences, Belgrade",
title = "Serbian black truffle Tuber aestivum: Microbiota and effects of different freezing regimes on volatile aroma compounds during storage, Srpski crni tartuf tuber aestivum: mikrobiota I uticaj različitih režima smrzavanja na isparljiiva aromatična jedinjenja tokom skladištenja",
volume = "68",
number = "3",
pages = "329-346",
doi = "10.2298/JAS2303329P"
}

Paunović, D., Mirković, M., Mirković, N., Tešević, V., Stanković Jeremić, J., Todosijević, M.,& Radulović, Z.. (2023). Serbian black truffle Tuber aestivum: Microbiota and effects of different freezing regimes on volatile aroma compounds during storage. in Journal of Agricultural Sciences, Belgrade
Belgrade : Serbian Chemical Society., 68(3), 329-346.
https://doi.org/10.2298/JAS2303329P

Paunović D, Mirković M, Mirković N, Tešević V, Stanković Jeremić J, Todosijević M, Radulović Z. Serbian black truffle Tuber aestivum: Microbiota and effects of different freezing regimes on volatile aroma compounds during storage. in Journal of Agricultural Sciences, Belgrade. 2023;68(3):329-346.
doi:10.2298/JAS2303329P .

Paunović, Dusanka, Mirković, Milica, Mirković, Nemanja, Tešević, Vele, Stanković Jeremić, Jovana, Todosijević, Marina, Radulović, Zorica, "Serbian black truffle Tuber aestivum: Microbiota and effects of different freezing regimes on volatile aroma compounds during storage" in Journal of Agricultural Sciences, Belgrade, 68, no. 3 (2023):329-346,
https://doi.org/10.2298/JAS2303329P . .

TY  - JOUR
AU  - Aćimović, Milica
AU  - Stanković Jeremić, Jovana
AU  - Miljković, Ana
AU  - Rat, Milica
AU  - Lončar, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7200
AB  - Ironwort (Sideritis montana L.), mountain germander (Teucrium montanum L.), wall germander (Teucrium chamaedrys L.), and horehound (Marrubium peregrinum L.) are species widely distributedacross Europe and are also found in North Africa and West Asia. Because of their wide distributionthey express significant chemical diversity. For generations, these plants have been used as medicalherbs for treating different aliments. The aim of this paper is to analyze volatile compounds of fourselected species that belong to the subfamily Lamioideae, family Lamiaceae, and inspect scientificallyproven biological activities and potential uses in modern phytotherapy in relation to traditionalmedicine. Therefore, in this research, we analyze the volatile compounds from this plants, obtainedin laboratory by a Clevenger-type apparatus, followed by liquid–liquid extraction with hexane as thesolvent. The identification of volatile compounds is conducted by GC-FID and GC-MS. Althoughthese plants are poor in essential oil, the most abundant class of volatile components are mainlysesquiterpenes: germacrene D (22.6%) in ironwort, 7-epi-trans-sesquisabinene hydrate (15.8%) inmountain germander, germacrene D (31.8%) and trans-caryophyllene (19.7%) in wall germander, andtrans-caryophyllene (32.4%) and trans-thujone (25.1%) in horehound. Furthermore, many studiesshow that, in addition to the essential oil, these plants contain phenols, flavonoids, diterpenes andditerpenoids, iridoids and their glycosides, coumarins, terpenes, and sterols, among other activecompounds, which affect biological activities. The other goal of this study is to review the literaturethat describes the traditional use of these plants in folk medicine in regions where they grow spontaneously and compare them with scientifically confirmed activities. Therefore, a bibliographic searchis conducted on Science Direct, PubMed, and Google Scholar to gather information related to thetopic and recommend potential applications in modern phytotherapy. In conclusion, we can say thatselected plants could be used as natural agents for promoting health, as a source of raw materialin the food industry, and as supplements, as well as in the pharmaceutical industry for developingplant-based remedies for prevention and treatment of many diseases, especially cancer.
PB  - Basel : MDPI
T2  - Molecules - Basel
T1  - Screening of Volatile Compounds, Traditional and Modern Phytotherapy Approaches of Selected Non-Aromatic Medicinal Plants (Lamiaceae, Lamioideae) from Rtanj Mountain, Eastern Serbia
VL  - 28
IS  - 12
SP  - 4611
DO  - 10.3390/molecules28124611
ER  - 

@article{
author = "Aćimović, Milica and Stanković Jeremić, Jovana and Miljković, Ana and Rat, Milica and Lončar, Biljana",
year = "2023",
abstract = "Ironwort (Sideritis montana L.), mountain germander (Teucrium montanum L.), wall germander (Teucrium chamaedrys L.), and horehound (Marrubium peregrinum L.) are species widely distributedacross Europe and are also found in North Africa and West Asia. Because of their wide distributionthey express significant chemical diversity. For generations, these plants have been used as medicalherbs for treating different aliments. The aim of this paper is to analyze volatile compounds of fourselected species that belong to the subfamily Lamioideae, family Lamiaceae, and inspect scientificallyproven biological activities and potential uses in modern phytotherapy in relation to traditionalmedicine. Therefore, in this research, we analyze the volatile compounds from this plants, obtainedin laboratory by a Clevenger-type apparatus, followed by liquid–liquid extraction with hexane as thesolvent. The identification of volatile compounds is conducted by GC-FID and GC-MS. Althoughthese plants are poor in essential oil, the most abundant class of volatile components are mainlysesquiterpenes: germacrene D (22.6%) in ironwort, 7-epi-trans-sesquisabinene hydrate (15.8%) inmountain germander, germacrene D (31.8%) and trans-caryophyllene (19.7%) in wall germander, andtrans-caryophyllene (32.4%) and trans-thujone (25.1%) in horehound. Furthermore, many studiesshow that, in addition to the essential oil, these plants contain phenols, flavonoids, diterpenes andditerpenoids, iridoids and their glycosides, coumarins, terpenes, and sterols, among other activecompounds, which affect biological activities. The other goal of this study is to review the literaturethat describes the traditional use of these plants in folk medicine in regions where they grow spontaneously and compare them with scientifically confirmed activities. Therefore, a bibliographic searchis conducted on Science Direct, PubMed, and Google Scholar to gather information related to thetopic and recommend potential applications in modern phytotherapy. In conclusion, we can say thatselected plants could be used as natural agents for promoting health, as a source of raw materialin the food industry, and as supplements, as well as in the pharmaceutical industry for developingplant-based remedies for prevention and treatment of many diseases, especially cancer.",
publisher = "Basel : MDPI",
journal = "Molecules - Basel",
title = "Screening of Volatile Compounds, Traditional and Modern Phytotherapy Approaches of Selected Non-Aromatic Medicinal Plants (Lamiaceae, Lamioideae) from Rtanj Mountain, Eastern Serbia",
volume = "28",
number = "12",
pages = "4611",
doi = "10.3390/molecules28124611"
}

Aćimović, M., Stanković Jeremić, J., Miljković, A., Rat, M.,& Lončar, B.. (2023). Screening of Volatile Compounds, Traditional and Modern Phytotherapy Approaches of Selected Non-Aromatic Medicinal Plants (Lamiaceae, Lamioideae) from Rtanj Mountain, Eastern Serbia. in Molecules - Basel
Basel : MDPI., 28(12), 4611.
https://doi.org/10.3390/molecules28124611

Aćimović M, Stanković Jeremić J, Miljković A, Rat M, Lončar B. Screening of Volatile Compounds, Traditional and Modern Phytotherapy Approaches of Selected Non-Aromatic Medicinal Plants (Lamiaceae, Lamioideae) from Rtanj Mountain, Eastern Serbia. in Molecules - Basel. 2023;28(12):4611.
doi:10.3390/molecules28124611 .

Aćimović, Milica, Stanković Jeremić, Jovana, Miljković, Ana, Rat, Milica, Lončar, Biljana, "Screening of Volatile Compounds, Traditional and Modern Phytotherapy Approaches of Selected Non-Aromatic Medicinal Plants (Lamiaceae, Lamioideae) from Rtanj Mountain, Eastern Serbia" in Molecules - Basel, 28, no. 12 (2023):4611,
https://doi.org/10.3390/molecules28124611 . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5681
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted
1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate.
The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel.
Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic
amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example
of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of
1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only
isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates
en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence
in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-
DHPs show blue-violet fluorescence with Φ = 0.09–0.81.
PB  - Great Britain : Royal Society of Chemistry
T2  - Organic & Biomolecular Chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
DO  - 10.1039/d2ob02119f
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted
1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate.
The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel.
Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic
amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example
of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of
1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only
isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates
en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence
in MeOH with the quantum yield Φ = 0.10–0.22 relative to quinine sulfate Φ = 0.58 and 1,4-
DHPs show blue-violet fluorescence with Φ = 0.09–0.81.",
publisher = "Great Britain : Royal Society of Chemistry",
journal = "Organic & Biomolecular Chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
doi = "10.1039/d2ob02119f"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry
Great Britain : Royal Society of Chemistry..
https://doi.org/10.1039/d2ob02119f

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & Biomolecular Chemistry. 2023;.
doi:10.1039/d2ob02119f .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & Biomolecular Chemistry (2023),
https://doi.org/10.1039/d2ob02119f . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Bošković, Jakša
AU  - Baranac-Stojanović, Marija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5790
AB  - We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10-0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09-0.81.
PB  - Royal Society of Chemistry
T2  - Organic & biomolecular chemistry
T1  - Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines
VL  - 21
IS  - 6
SP  - 1187
EP  - 1205
DO  - 10.1039/d2ob02119f
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Bošković, Jakša and Baranac-Stojanović, Marija",
year = "2023",
abstract = "We present the green, highly atom-economical, solid-state silica gel-catalyzed synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines and ethyl propiolate. The DHP skeleton was assembled by heating the reactants and silica gel in a closed vessel. Aliphatic amines provided 1,4-isomers as the main or only DHP products, but the reactions of aromatic amines yielded a mixture of 1,4- and 1,2-isomers. To the best of our knowledge, this is the first example of the formation of a 1,2-DHP structure by the reaction of an amine with propiolic ester. Addition of 1 mass percent of H2SO4 to silica gel shifted the product distribution to 1,4-DHP as the main or the only isomer obtained. Experimental and theoretical analyses led to the identification of two key intermediates en route to DHPs and the explanation of the observed regioisomeric ratios. 1,2-DHPs show blue-cyan fluorescence in MeOH with the quantum yield Φ = 0.10-0.22 relative to quinine sulfate Φ = 0.58 and 1,4-DHPs show blue-violet fluorescence with Φ = 0.09-0.81.",
publisher = "Royal Society of Chemistry",
journal = "Organic & biomolecular chemistry",
title = "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines",
volume = "21",
number = "6",
pages = "1187-1205",
doi = "10.1039/d2ob02119f"
}

Aleksić, J., Stojanović, M., Bošković, J.,& Baranac-Stojanović, M.. (2023). Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & biomolecular chemistry
Royal Society of Chemistry., 21(6), 1187-1205.
https://doi.org/10.1039/d2ob02119f

Aleksić J, Stojanović M, Bošković J, Baranac-Stojanović M. Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines. in Organic & biomolecular chemistry. 2023;21(6):1187-1205.
doi:10.1039/d2ob02119f .

Aleksić, Jovana, Stojanović, Milovan, Bošković, Jakša, Baranac-Stojanović, Marija, "Solid-state silica gel-catalyzed synthesis of fluorescent polysubstituted 1,4- and 1,2-dihydropyridines" in Organic & biomolecular chemistry, 21, no. 6 (2023):1187-1205,
https://doi.org/10.1039/d2ob02119f . .

TY  - JOUR
AU  - Aćimović, Milica
AU  - Semerdijeva, Ivanka
AU  - Zheljazkov, Valtcho D.
AU  - Rat, Milica
AU  - Stanković Jeremić, Jovana
AU  - Lončar, Biljana
AU  - Vukić, Vladimir
AU  - Radovanović, Katarina
AU  - Gavarić, Neda
AU  - Pezo, Lato
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6679
AB  - This research investigated a Balkan endemic species, Achillea clypeolata, collected from two locations (Dobrostan and Ivaylovgrad) in Bulgaria and two locations (Ozren and Rtanj) in Serbia. The goal was to compare the essential oil (EO) of A. clypeolata from these four localities. The EO was isolated from dry aboveground plant parts by hydrodistillation, and the identification of the EO constituents was carried out by GC-MS analyses. Principal Component Analysis (PCA), correlation analysis, and an unrooted cluster tree were used to define distinctions in the presence of volatile compounds in A. clypeolata EO. Results showed that A. clypeolata of Serbian origin (Ozren and Rtanj) contained 1,8-cineole as the main constituent, and belonged to the previously described 1,8-cineole as a dominant compound in the EO profile. On the other hand, the results from Bulgaria show an evident chemical diversification within the A. clypeolata species, as 1,8-cineole (23.2%), camphor (5.0%) and borneol (8.9%) prevailed in the EO of the studied samples collected from Ivaylovgrad, while borneol (22.6%), β-eudesmol (12.7%) and elemol (7.8%) were the main ones in the EO from Dobrostan. In sillico analysis revealed the high anti-inflammatory potential of A. clypeolata, which may be highly diverse depending on the population and active compounds it contains.
PB  - Elsevier BV
T2  - Biochemical Systematics and Ecology
T1  - Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm
VL  - 110
SP  - 104679
DO  - 10.1016/j.bse.2023.104679
ER  - 

@article{
author = "Aćimović, Milica and Semerdijeva, Ivanka and Zheljazkov, Valtcho D. and Rat, Milica and Stanković Jeremić, Jovana and Lončar, Biljana and Vukić, Vladimir and Radovanović, Katarina and Gavarić, Neda and Pezo, Lato",
year = "2023",
abstract = "This research investigated a Balkan endemic species, Achillea clypeolata, collected from two locations (Dobrostan and Ivaylovgrad) in Bulgaria and two locations (Ozren and Rtanj) in Serbia. The goal was to compare the essential oil (EO) of A. clypeolata from these four localities. The EO was isolated from dry aboveground plant parts by hydrodistillation, and the identification of the EO constituents was carried out by GC-MS analyses. Principal Component Analysis (PCA), correlation analysis, and an unrooted cluster tree were used to define distinctions in the presence of volatile compounds in A. clypeolata EO. Results showed that A. clypeolata of Serbian origin (Ozren and Rtanj) contained 1,8-cineole as the main constituent, and belonged to the previously described 1,8-cineole as a dominant compound in the EO profile. On the other hand, the results from Bulgaria show an evident chemical diversification within the A. clypeolata species, as 1,8-cineole (23.2%), camphor (5.0%) and borneol (8.9%) prevailed in the EO of the studied samples collected from Ivaylovgrad, while borneol (22.6%), β-eudesmol (12.7%) and elemol (7.8%) were the main ones in the EO from Dobrostan. In sillico analysis revealed the high anti-inflammatory potential of A. clypeolata, which may be highly diverse depending on the population and active compounds it contains.",
publisher = "Elsevier BV",
journal = "Biochemical Systematics and Ecology",
title = "Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm",
volume = "110",
pages = "104679",
doi = "10.1016/j.bse.2023.104679"
}

Aćimović, M., Semerdijeva, I., Zheljazkov, V. D., Rat, M., Stanković Jeremić, J., Lončar, B., Vukić, V., Radovanović, K., Gavarić, N.,& Pezo, L.. (2023). Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm. in Biochemical Systematics and Ecology
Elsevier BV., 110, 104679.
https://doi.org/10.1016/j.bse.2023.104679

Aćimović M, Semerdijeva I, Zheljazkov VD, Rat M, Stanković Jeremić J, Lončar B, Vukić V, Radovanović K, Gavarić N, Pezo L. Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm. in Biochemical Systematics and Ecology. 2023;110:104679.
doi:10.1016/j.bse.2023.104679 .

Aćimović, Milica, Semerdijeva, Ivanka, Zheljazkov, Valtcho D., Rat, Milica, Stanković Jeremić, Jovana, Lončar, Biljana, Vukić, Vladimir, Radovanović, Katarina, Gavarić, Neda, Pezo, Lato, "Variation in the essential oil composition and in silico analysis of anti-inflammatory potential of Balkan endemic species Achillea clypeolata Sm" in Biochemical Systematics and Ecology, 110 (2023):104679,
https://doi.org/10.1016/j.bse.2023.104679 . .

TY  - JOUR
AU  - Nikolić, Biljana M.
AU  - Ballian, Dalibor A.
AU  - Đorđević, Iris
AU  - Rajčević, Nemanja
AU  - Todosijević, Marina M.
AU  - Stanković Jeremić, Jovana
AU  - Mitić, Zorica S.
AU  - Bojović, Srđan
AU  - Tešević, Vele
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6680
AB  - Population variability of n-alkanes in the cuticular waxes of Serbian spruce needles from Bosnia and Herzegovina was investigated for the first time. n-Alkanes exhibited composition variability ranging from C18 to C35. The divergence of populations from Bosnia and Herzegovina and previously investigated Serbian populations was statistically confirmed by PCA, DA, and CA (Cluster analysis), which could support the fact that there are two possible spruce chemotypes: one relating to the Bosnian-Herzegovinian and the other to the Serbian populations. Climate parameters (precipitation, temperature, wind, and solar radiation) approved this conclusion.
PB  - Elsevier Ltd.
T2  - Biochemical Systematics and Ecology
T1  - n-Alkanes variability in natural populations of Picea omorika (Pančić) Purk. From Bosnia and Herzegovina
VL  - 106
SP  - 104544
DO  - 10.1016/j.bse.2022.104544
ER  - 

@article{
author = "Nikolić, Biljana M. and Ballian, Dalibor A. and Đorđević, Iris and Rajčević, Nemanja and Todosijević, Marina M. and Stanković Jeremić, Jovana and Mitić, Zorica S. and Bojović, Srđan and Tešević, Vele",
year = "2023",
abstract = "Population variability of n-alkanes in the cuticular waxes of Serbian spruce needles from Bosnia and Herzegovina was investigated for the first time. n-Alkanes exhibited composition variability ranging from C18 to C35. The divergence of populations from Bosnia and Herzegovina and previously investigated Serbian populations was statistically confirmed by PCA, DA, and CA (Cluster analysis), which could support the fact that there are two possible spruce chemotypes: one relating to the Bosnian-Herzegovinian and the other to the Serbian populations. Climate parameters (precipitation, temperature, wind, and solar radiation) approved this conclusion.",
publisher = "Elsevier Ltd.",
journal = "Biochemical Systematics and Ecology",
title = "n-Alkanes variability in natural populations of Picea omorika (Pančić) Purk. From Bosnia and Herzegovina",
volume = "106",
pages = "104544",
doi = "10.1016/j.bse.2022.104544"
}

Nikolić, B. M., Ballian, D. A., Đorđević, I., Rajčević, N., Todosijević, M. M., Stanković Jeremić, J., Mitić, Z. S., Bojović, S.,& Tešević, V.. (2023). n-Alkanes variability in natural populations of Picea omorika (Pančić) Purk. From Bosnia and Herzegovina. in Biochemical Systematics and Ecology
Elsevier Ltd.., 106, 104544.
https://doi.org/10.1016/j.bse.2022.104544

Nikolić BM, Ballian DA, Đorđević I, Rajčević N, Todosijević MM, Stanković Jeremić J, Mitić ZS, Bojović S, Tešević V. n-Alkanes variability in natural populations of Picea omorika (Pančić) Purk. From Bosnia and Herzegovina. in Biochemical Systematics and Ecology. 2023;106:104544.
doi:10.1016/j.bse.2022.104544 .

Nikolić, Biljana M., Ballian, Dalibor A., Đorđević, Iris, Rajčević, Nemanja, Todosijević, Marina M., Stanković Jeremić, Jovana, Mitić, Zorica S., Bojović, Srđan, Tešević, Vele, "n-Alkanes variability in natural populations of Picea omorika (Pančić) Purk. From Bosnia and Herzegovina" in Biochemical Systematics and Ecology, 106 (2023):104544,
https://doi.org/10.1016/j.bse.2022.104544 . .

TY  - JOUR
AU  - Krstić, Gordana
AU  - Nikolić, Biljana
AU  - Todosijević, Marina
AU  - Mitić, Zorica
AU  - Stanković Jeremić, Jovana
AU  - Cvetković, Mirjana
AU  - Bojović, Srđan
AU  - Marin, Petar
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5428
AB  - In this study we have reported the chemical composition of the essential oils obtained from the needles of twelve Pinus taxa, belonging to the subgenera Pinus (sections Pinus and Trifoliae) and Strobus (sect. Quinquefoliae). Monoterpenes dominated over sesquiterpenes in most of the investigated taxa of both subgenera, except in representatives of the subsection Pinaster, subgenus Pinus. α-Pinene was the most abundant terpene in eight pines, but other dominant terpenes were found in some taxa - trans-caryophyllene, germacrene D, abietadiene and β-pinene. In the subsect. Pinaster, the most dominant compounds varied from species to species. In addition, P. halepensis and P. pinaster had the highest percentage of diterpenes, while P. heldreichii was the richest in germacrene D. In the PCA and cluster analyses, three species from the subsect. Pinaster emerged as the most distant: P. halepensis, P. pinaster, and P. heldreichii. In addition, the possible taxonomic implications of the terpene profile in the analysed Pinus taxa were also discussed.
AB  - U ovom proučavanju objavili smo hemijski sastav etarskih ulja dobijenih iz iglica 12 taksona roda Pinus, koji pripadaju podrodovima Pinus
(sekcije Pinus i Trifoliae) i Strobus (sekcija Quinquefoliae). U većini istraživanih taksona monoterpeni dominiraju nad seskviterpenima kod
oba podroda, osim kod uzoraka podsekcije Pinaster podroda Pinus. α-Pinen je najobilniji kod 8 borova, ali kod nekih taksona dominantni su
trans-kariofilen, germakren D, abietadien i β-pinen. U subcekciji Pinaster dominantne komponente variraju od vrste do vrste. Nadalje, P. halepensis
i P. pinaster imaju najveći procenat diterpena, dok je P. heldreichii najbogatiji u germakrenu D. U PCA i klaster analizama pokazale su
se najudaljenije tri vrste subsekcije Pinaster: P. halepensis, P. pinaster i P. heldreichii. Nadalje, u analiziranim vrstama roda Pinus diskutovane
su moguće taksonomske implikacije terpenskog profila.
PB  - Belgrade :  Institute of Botany and Botanical Garden "Jevremovac"
T2  - Botanica Serbia
T1  - Terpene relationships among some soft and hard pine species
T1  - Terpenski odnosi između nekih mekih i tvrdih borova
VL  - 46
IS  - 1
SP  - 39
EP  - 48
DO  - 10.2298/BOTSERB2201039K
ER  - 

@article{
author = "Krstić, Gordana and Nikolić, Biljana and Todosijević, Marina and Mitić, Zorica and Stanković Jeremić, Jovana and Cvetković, Mirjana and Bojović, Srđan and Marin, Petar",
year = "2022",
abstract = "In this study we have reported the chemical composition of the essential oils obtained from the needles of twelve Pinus taxa, belonging to the subgenera Pinus (sections Pinus and Trifoliae) and Strobus (sect. Quinquefoliae). Monoterpenes dominated over sesquiterpenes in most of the investigated taxa of both subgenera, except in representatives of the subsection Pinaster, subgenus Pinus. α-Pinene was the most abundant terpene in eight pines, but other dominant terpenes were found in some taxa - trans-caryophyllene, germacrene D, abietadiene and β-pinene. In the subsect. Pinaster, the most dominant compounds varied from species to species. In addition, P. halepensis and P. pinaster had the highest percentage of diterpenes, while P. heldreichii was the richest in germacrene D. In the PCA and cluster analyses, three species from the subsect. Pinaster emerged as the most distant: P. halepensis, P. pinaster, and P. heldreichii. In addition, the possible taxonomic implications of the terpene profile in the analysed Pinus taxa were also discussed., U ovom proučavanju objavili smo hemijski sastav etarskih ulja dobijenih iz iglica 12 taksona roda Pinus, koji pripadaju podrodovima Pinus
(sekcije Pinus i Trifoliae) i Strobus (sekcija Quinquefoliae). U većini istraživanih taksona monoterpeni dominiraju nad seskviterpenima kod
oba podroda, osim kod uzoraka podsekcije Pinaster podroda Pinus. α-Pinen je najobilniji kod 8 borova, ali kod nekih taksona dominantni su
trans-kariofilen, germakren D, abietadien i β-pinen. U subcekciji Pinaster dominantne komponente variraju od vrste do vrste. Nadalje, P. halepensis
i P. pinaster imaju najveći procenat diterpena, dok je P. heldreichii najbogatiji u germakrenu D. U PCA i klaster analizama pokazale su
se najudaljenije tri vrste subsekcije Pinaster: P. halepensis, P. pinaster i P. heldreichii. Nadalje, u analiziranim vrstama roda Pinus diskutovane
su moguće taksonomske implikacije terpenskog profila.",
publisher = "Belgrade :  Institute of Botany and Botanical Garden "Jevremovac"",
journal = "Botanica Serbia",
title = "Terpene relationships among some soft and hard pine species, Terpenski odnosi između nekih mekih i tvrdih borova",
volume = "46",
number = "1",
pages = "39-48",
doi = "10.2298/BOTSERB2201039K"
}

Krstić, G., Nikolić, B., Todosijević, M., Mitić, Z., Stanković Jeremić, J., Cvetković, M., Bojović, S.,& Marin, P.. (2022). Terpene relationships among some soft and hard pine species. in Botanica Serbia
Belgrade :  Institute of Botany and Botanical Garden "Jevremovac"., 46(1), 39-48.
https://doi.org/10.2298/BOTSERB2201039K

Krstić G, Nikolić B, Todosijević M, Mitić Z, Stanković Jeremić J, Cvetković M, Bojović S, Marin P. Terpene relationships among some soft and hard pine species. in Botanica Serbia. 2022;46(1):39-48.
doi:10.2298/BOTSERB2201039K .

Krstić, Gordana, Nikolić, Biljana, Todosijević, Marina, Mitić, Zorica, Stanković Jeremić, Jovana, Cvetković, Mirjana, Bojović, Srđan, Marin, Petar, "Terpene relationships among some soft and hard pine species" in Botanica Serbia, 46, no. 1 (2022):39-48,
https://doi.org/10.2298/BOTSERB2201039K . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5365
AB  - Aromaticity rules in the ground singlet state and the first excited triplet state are exactly opposite, as shown by Baird. Thus, (4n + 2)π electron annulenes are antiaromatic and 4nπ annulenes are aromatic in their triplet state. In this work, we employ quantum-mechanical calculations at the density functional theory (DFT) level to examine (anti)aromaticity of singlet and triplet corannulene dianion and dication in their bowl-shaped ground-state structure and planar transition-state structure. We find that singlet dianion contains aromatic hub and antiaromatic rim, whereas singlet dication is an antiaromatic system. This agrees with previous calculations of current density induced by perpendicular magnetic field. For triplet dianion, we find that it can be described as having aromatic rim and nonaromatic hub. Triplet dication was found to be nonaromatic, though in planar transition-state structure, locally and semiglobally antiaromatic naphthalene subunit and aromatic central ring can be discerned.
PB  - John Wiley and Sons Ltd
T2  - Journal of Physical Organic Chemistry
T1  - Aromaticity study of singlet- and triplet-state corannulene dianion and dication
DO  - 10.1002/poc.4434
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2022",
abstract = "Aromaticity rules in the ground singlet state and the first excited triplet state are exactly opposite, as shown by Baird. Thus, (4n + 2)π electron annulenes are antiaromatic and 4nπ annulenes are aromatic in their triplet state. In this work, we employ quantum-mechanical calculations at the density functional theory (DFT) level to examine (anti)aromaticity of singlet and triplet corannulene dianion and dication in their bowl-shaped ground-state structure and planar transition-state structure. We find that singlet dianion contains aromatic hub and antiaromatic rim, whereas singlet dication is an antiaromatic system. This agrees with previous calculations of current density induced by perpendicular magnetic field. For triplet dianion, we find that it can be described as having aromatic rim and nonaromatic hub. Triplet dication was found to be nonaromatic, though in planar transition-state structure, locally and semiglobally antiaromatic naphthalene subunit and aromatic central ring can be discerned.",
publisher = "John Wiley and Sons Ltd",
journal = "Journal of Physical Organic Chemistry",
title = "Aromaticity study of singlet- and triplet-state corannulene dianion and dication",
doi = "10.1002/poc.4434"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2022). Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry
John Wiley and Sons Ltd..
https://doi.org/10.1002/poc.4434

Aleksić J, Stojanović M, Baranac-Stojanović M. Aromaticity study of singlet- and triplet-state corannulene dianion and dication. in Journal of Physical Organic Chemistry. 2022;.
doi:10.1002/poc.4434 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Aromaticity study of singlet- and triplet-state corannulene dianion and dication" in Journal of Physical Organic Chemistry (2022),
https://doi.org/10.1002/poc.4434 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5408
AB  - By employing density functional theory (DFT)
calculations we show that mono- and disilicon substitution in
polycyclic aromatic hydrocarbons, having two to four
benzene units, quenches their triplet state antiaromaticity by
creating Huckel aromatic (poly)benzenoid subunit(s) and
weakly antiaromatic, or almost nonaromatic silacycle. Therefore,
such systems are predicted to be globally aromatic in
both the ground state and the first excited triplet state.
Putting the silicon atom(s) into various positions of a hydrocarbon
provides an opportunity to tune the singlet-triplet
energy gaps. They depend on the global aromaticity degree
which, in turn, depends on the type of aromatic carbocyclic
subunit(s) and the extent of their aromaticity. On the basis of
the set of studied compounds, some preliminary rules on
how to regulate the extent of global, semiglobal and local
aromaticity are proposed. The results of this work extend the
importance of Huckel aromaticity concept to excited triplet
states which are usually characterized by the Baird type of
(anti)aromaticity.
PB  - Wiley
T2  - Chemistry- An Asian Journal
T1  - Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution
SP  - e202101261
DO  - 10.1002/asia.202101261
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2022",
abstract = "By employing density functional theory (DFT)
calculations we show that mono- and disilicon substitution in
polycyclic aromatic hydrocarbons, having two to four
benzene units, quenches their triplet state antiaromaticity by
creating Huckel aromatic (poly)benzenoid subunit(s) and
weakly antiaromatic, or almost nonaromatic silacycle. Therefore,
such systems are predicted to be globally aromatic in
both the ground state and the first excited triplet state.
Putting the silicon atom(s) into various positions of a hydrocarbon
provides an opportunity to tune the singlet-triplet
energy gaps. They depend on the global aromaticity degree
which, in turn, depends on the type of aromatic carbocyclic
subunit(s) and the extent of their aromaticity. On the basis of
the set of studied compounds, some preliminary rules on
how to regulate the extent of global, semiglobal and local
aromaticity are proposed. The results of this work extend the
importance of Huckel aromaticity concept to excited triplet
states which are usually characterized by the Baird type of
(anti)aromaticity.",
publisher = "Wiley",
journal = "Chemistry- An Asian Journal",
title = "Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution",
pages = "e202101261",
doi = "10.1002/asia.202101261"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2022). Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution. in Chemistry- An Asian Journal
Wiley., e202101261.
https://doi.org/10.1002/asia.202101261

Baranac-Stojanović M, Stojanović M, Aleksić J. Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution. in Chemistry- An Asian Journal. 2022;:e202101261.
doi:10.1002/asia.202101261 .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Revival of Hückel Aromatic (Poly)benzenoid Subunits in Triplet State Polycyclic Aromatic Hydrocarbons by Silicon Substitution" in Chemistry- An Asian Journal (2022):e202101261,
https://doi.org/10.1002/asia.202101261 . .

TY  - JOUR
AU  - Aćimović, Milica
AU  - Stanković Jeremić, Jovana
AU  - Todosijević, Marina
AU  - Kiprovski, Biljana
AU  - Vidović, Senka
AU  - Vladić, Jelena
AU  - Pezo, Lato
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5407
AB  - The most abundant volatile compounds of sweet wormwood (Artemisia annua L.) essential oil were artemisia ketone (25.4 %) and trans-caryophyllene (10.2 %), followed by 1,8-cineole, camphor, germacrene D and β-selinene. The major volatile compounds in the hydrosol were camphor (25.1 %), 1,8-cineole (20.5 %) and artemisia ketone (10.7 %), followed by trans-pinocarveol and yomogi alcohol. Tested essential oil was rich in oxygenated monoterpenes and sesquiterpene hydrocarbons, while the former were identified as the major class of volatile compounds in the hydrosol, due to higher water solubility. Classification of all sweet wormwood chemotypes, according to essential oil composition, in available literature (17 studies and 61 accessions) could be done according to four chemotypes: artemisia ketone+artemisia alcohol (most abundant), artemisia ketone, camphor and nonspecific chemotype. According to this classification, essential oil of sweet wormwood from this study belongs to artemisia ketone (content varied between 22.1 and 55.8 %). Bearing in mind that hydrosols are a by-product of industrial production of essential oils, and the fact that sweet wormwood hydrosol has high contents of camphor, 1,8-cineole and artemisia ketone, there is a great potential for the use of this aromatic plant primary processing waste product as a water replacement in cosmetic industry, beverages flavoring, for food preservation, as well as in post-harvest pre-storage treatments in organic agriculture.
PB  - Wiley
T2  - Chemistry and Biodiversity
T1  - Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia
VL  - 19
IS  - 3
SP  - e202100954
DO  - 10.1002/cbdv.202100954
ER  - 

@article{
author = "Aćimović, Milica and Stanković Jeremić, Jovana and Todosijević, Marina and Kiprovski, Biljana and Vidović, Senka and Vladić, Jelena and Pezo, Lato",
year = "2022",
abstract = "The most abundant volatile compounds of sweet wormwood (Artemisia annua L.) essential oil were artemisia ketone (25.4 %) and trans-caryophyllene (10.2 %), followed by 1,8-cineole, camphor, germacrene D and β-selinene. The major volatile compounds in the hydrosol were camphor (25.1 %), 1,8-cineole (20.5 %) and artemisia ketone (10.7 %), followed by trans-pinocarveol and yomogi alcohol. Tested essential oil was rich in oxygenated monoterpenes and sesquiterpene hydrocarbons, while the former were identified as the major class of volatile compounds in the hydrosol, due to higher water solubility. Classification of all sweet wormwood chemotypes, according to essential oil composition, in available literature (17 studies and 61 accessions) could be done according to four chemotypes: artemisia ketone+artemisia alcohol (most abundant), artemisia ketone, camphor and nonspecific chemotype. According to this classification, essential oil of sweet wormwood from this study belongs to artemisia ketone (content varied between 22.1 and 55.8 %). Bearing in mind that hydrosols are a by-product of industrial production of essential oils, and the fact that sweet wormwood hydrosol has high contents of camphor, 1,8-cineole and artemisia ketone, there is a great potential for the use of this aromatic plant primary processing waste product as a water replacement in cosmetic industry, beverages flavoring, for food preservation, as well as in post-harvest pre-storage treatments in organic agriculture.",
publisher = "Wiley",
journal = "Chemistry and Biodiversity",
title = "Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia",
volume = "19",
number = "3",
pages = "e202100954",
doi = "10.1002/cbdv.202100954"
}

Aćimović, M., Stanković Jeremić, J., Todosijević, M., Kiprovski, B., Vidović, S., Vladić, J.,& Pezo, L.. (2022). Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia. in Chemistry and Biodiversity
Wiley., 19(3), e202100954.
https://doi.org/10.1002/cbdv.202100954

Aćimović M, Stanković Jeremić J, Todosijević M, Kiprovski B, Vidović S, Vladić J, Pezo L. Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia. in Chemistry and Biodiversity. 2022;19(3):e202100954.
doi:10.1002/cbdv.202100954 .

Aćimović, Milica, Stanković Jeremić, Jovana, Todosijević, Marina, Kiprovski, Biljana, Vidović, Senka, Vladić, Jelena, Pezo, Lato, "Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia" in Chemistry and Biodiversity, 19, no. 3 (2022):e202100954,
https://doi.org/10.1002/cbdv.202100954 . .

TY  - JOUR
AU  - Aćimović, Milica
AU  - Lončar, Biljana
AU  - Stanković Jeremić, Jovana
AU  - Cvetković, Mirjana
AU  - Pezo, Lato
AU  - Pezo, Milada
AU  - Todosijević, Marina
AU  - Tešević, Vele
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5409
AB  - Lavandula sp. essential oil and hydrolate are commercially valuable in various industry
branches with the potential for wide-ranging applications. This study aimed to evaluate the quality
of these products obtained from L. x intermedia cv. ‘Budrovka’ for the first time cultivated on Fruška
Gora Mt. (Serbia) during three successive seasons (2019, 2020, and 2021). Essential oil extraction
was obtained by steam distillation, and the composition and influence of weather conditions were
also assessed, using flowering tops. The obtained essential oils and hydrolates were analysed by
gas chromatography with a flame ionization detector (GC-FID) and gas chromatography coupled to
mass spectrometry (GC-MS). A linear regression model was developed to predict L. x intermedia cv.
‘Budrovka’ essential oil volatile compound content and hydrolate composition during three years,
according to temperature and precipitation data, and the appropriate regression coefficients were
calculated, while the correlation analysis was employed to analyse the correlations in hydrolate
and essential oil compounds. To completely describe the structure of the research data that would
present a better insight into the similarities and differences among the diverse L. x intermedia cv.
‘Budrovka’ samples, the PCA was used. The most dominant in L. intermedia cv. ‘Budrovka’ essential
oil and hydrolate were oxygenated monoterpenes: linalool, 1,8-cineole, borneol, linalyl acetate, and
terpinene-4-ol. It is established that the temperature was positively correlated with all essential oil
and hydrolate compounds. The precipitations were positively correlated with the main compounds
(linalool, 1,8-cineole, and borneol), while the other compounds’ content negatively correlated to
precipitation. The results indicated that Fruška Gora Mt. has suitable agro-ecological requirements
for cultivating Lavandula sp. and providing satisfactory essential oil and hydrolate.
PB  - Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)
T2  - Horticulturae
T1  - Weather Conditions Influence on Lavandin Essential Oil and Hydrolate Quality
VL  - 8
SP  - 281
DO  - 10.3390/horticulturae8040281
ER  - 

@article{
author = "Aćimović, Milica and Lončar, Biljana and Stanković Jeremić, Jovana and Cvetković, Mirjana and Pezo, Lato and Pezo, Milada and Todosijević, Marina and Tešević, Vele",
year = "2022",
abstract = "Lavandula sp. essential oil and hydrolate are commercially valuable in various industry
branches with the potential for wide-ranging applications. This study aimed to evaluate the quality
of these products obtained from L. x intermedia cv. ‘Budrovka’ for the first time cultivated on Fruška
Gora Mt. (Serbia) during three successive seasons (2019, 2020, and 2021). Essential oil extraction
was obtained by steam distillation, and the composition and influence of weather conditions were
also assessed, using flowering tops. The obtained essential oils and hydrolates were analysed by
gas chromatography with a flame ionization detector (GC-FID) and gas chromatography coupled to
mass spectrometry (GC-MS). A linear regression model was developed to predict L. x intermedia cv.
‘Budrovka’ essential oil volatile compound content and hydrolate composition during three years,
according to temperature and precipitation data, and the appropriate regression coefficients were
calculated, while the correlation analysis was employed to analyse the correlations in hydrolate
and essential oil compounds. To completely describe the structure of the research data that would
present a better insight into the similarities and differences among the diverse L. x intermedia cv.
‘Budrovka’ samples, the PCA was used. The most dominant in L. intermedia cv. ‘Budrovka’ essential
oil and hydrolate were oxygenated monoterpenes: linalool, 1,8-cineole, borneol, linalyl acetate, and
terpinene-4-ol. It is established that the temperature was positively correlated with all essential oil
and hydrolate compounds. The precipitations were positively correlated with the main compounds
(linalool, 1,8-cineole, and borneol), while the other compounds’ content negatively correlated to
precipitation. The results indicated that Fruška Gora Mt. has suitable agro-ecological requirements
for cultivating Lavandula sp. and providing satisfactory essential oil and hydrolate.",
publisher = "Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)",
journal = "Horticulturae",
title = "Weather Conditions Influence on Lavandin Essential Oil and Hydrolate Quality",
volume = "8",
pages = "281",
doi = "10.3390/horticulturae8040281"
}

Aćimović, M., Lončar, B., Stanković Jeremić, J., Cvetković, M., Pezo, L., Pezo, M., Todosijević, M.,& Tešević, V.. (2022). Weather Conditions Influence on Lavandin Essential Oil and Hydrolate Quality. in Horticulturae
Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)., 8, 281.
https://doi.org/10.3390/horticulturae8040281

Aćimović M, Lončar B, Stanković Jeremić J, Cvetković M, Pezo L, Pezo M, Todosijević M, Tešević V. Weather Conditions Influence on Lavandin Essential Oil and Hydrolate Quality. in Horticulturae. 2022;8:281.
doi:10.3390/horticulturae8040281 .

Aćimović, Milica, Lončar, Biljana, Stanković Jeremić, Jovana, Cvetković, Mirjana, Pezo, Lato, Pezo, Milada, Todosijević, Marina, Tešević, Vele, "Weather Conditions Influence on Lavandin Essential Oil and Hydrolate Quality" in Horticulturae, 8 (2022):281,
https://doi.org/10.3390/horticulturae8040281 . .

TY  - JOUR
AU  - Aćimović, Milica
AU  - Pezo, Lato
AU  - Čabarkapa, Ivana
AU  - Trudić, Anika
AU  - Stanković Jeremić, Jovana
AU  - Varga, Ana
AU  - Lončar, Biljana
AU  - Šovljanski, Olja
AU  - Tešević, Vele
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5587
AB  - This study aimed to investigate the chemical composition of steam distillate essential oil and corresponding hydrolate obtained from S. officinalis grown in Serbia, as well as the influence of weather conditions (temperature and precipitations) on their chemical profiles. Furthermore, their antimicrobial activity was investigated in vitro. The main compounds in essential oil were cis-thujone, followed by camphor, trans-thujone, and 1,8-cineole, while hydrolate was slightly different from the essential oil, with camphor, cis-thujone, and 1,8-cineole as the main compounds. Among the eight respiratory-associated microorganisms, Klebsiella oxytoca was the most sensitive to the tested EOs (minimum inhibitory concentration (MIC)/minimal bactericidal/fungicidal concentration (MBC/MFC) were 14.20 and 28.4 μL mL−1, respectively). MIC and MBC values of other tested bacteria ranged between 28.40 and 227.25 μL mL−1 while for Candida albicans MIC/MFC ranged from 28.40/56.81 to 56.81–113.63 μL mL−1. Antibiotic susceptibility patterns for the analyzed eight respiratory-associated microorganisms showed an intermediate level of resistance to commonly used antibiotics such as ampicillin, levofloxacin, and ciprofloxacin. As a preliminary approach to the antimicrobial profiling of the tested EO, the obtained results revealed that the tested samples possess remarkable antibacterial activities and could be used to develop pharmaceutical formulations as an alternative to conventional antibiotic therapy.
PB  - MDPI AG
T2  - Processes
T1  - Variation of Salvia officinalis L. Essential Oil and Hydrolate Composition and Their Antimicrobial Activity
VL  - 10
IS  - 8
SP  - 1608
DO  - 10.3390/pr10081608
ER  - 

@article{
author = "Aćimović, Milica and Pezo, Lato and Čabarkapa, Ivana and Trudić, Anika and Stanković Jeremić, Jovana and Varga, Ana and Lončar, Biljana and Šovljanski, Olja and Tešević, Vele",
year = "2022",
abstract = "This study aimed to investigate the chemical composition of steam distillate essential oil and corresponding hydrolate obtained from S. officinalis grown in Serbia, as well as the influence of weather conditions (temperature and precipitations) on their chemical profiles. Furthermore, their antimicrobial activity was investigated in vitro. The main compounds in essential oil were cis-thujone, followed by camphor, trans-thujone, and 1,8-cineole, while hydrolate was slightly different from the essential oil, with camphor, cis-thujone, and 1,8-cineole as the main compounds. Among the eight respiratory-associated microorganisms, Klebsiella oxytoca was the most sensitive to the tested EOs (minimum inhibitory concentration (MIC)/minimal bactericidal/fungicidal concentration (MBC/MFC) were 14.20 and 28.4 μL mL−1, respectively). MIC and MBC values of other tested bacteria ranged between 28.40 and 227.25 μL mL−1 while for Candida albicans MIC/MFC ranged from 28.40/56.81 to 56.81–113.63 μL mL−1. Antibiotic susceptibility patterns for the analyzed eight respiratory-associated microorganisms showed an intermediate level of resistance to commonly used antibiotics such as ampicillin, levofloxacin, and ciprofloxacin. As a preliminary approach to the antimicrobial profiling of the tested EO, the obtained results revealed that the tested samples possess remarkable antibacterial activities and could be used to develop pharmaceutical formulations as an alternative to conventional antibiotic therapy.",
publisher = "MDPI AG",
journal = "Processes",
title = "Variation of Salvia officinalis L. Essential Oil and Hydrolate Composition and Their Antimicrobial Activity",
volume = "10",
number = "8",
pages = "1608",
doi = "10.3390/pr10081608"
}

Aćimović, M., Pezo, L., Čabarkapa, I., Trudić, A., Stanković Jeremić, J., Varga, A., Lončar, B., Šovljanski, O.,& Tešević, V.. (2022). Variation of Salvia officinalis L. Essential Oil and Hydrolate Composition and Their Antimicrobial Activity. in Processes
MDPI AG., 10(8), 1608.
https://doi.org/10.3390/pr10081608

Aćimović M, Pezo L, Čabarkapa I, Trudić A, Stanković Jeremić J, Varga A, Lončar B, Šovljanski O, Tešević V. Variation of Salvia officinalis L. Essential Oil and Hydrolate Composition and Their Antimicrobial Activity. in Processes. 2022;10(8):1608.
doi:10.3390/pr10081608 .

Aćimović, Milica, Pezo, Lato, Čabarkapa, Ivana, Trudić, Anika, Stanković Jeremić, Jovana, Varga, Ana, Lončar, Biljana, Šovljanski, Olja, Tešević, Vele, "Variation of Salvia officinalis L. Essential Oil and Hydrolate Composition and Their Antimicrobial Activity" in Processes, 10, no. 8 (2022):1608,
https://doi.org/10.3390/pr10081608 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4483
AB  - Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically
important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and
anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the
density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity
and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization
results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity
and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches
nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to
accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to
develop local aromaticity, which, when combined with nonaromatic silacycle and weak global
antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease
with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.
PB  - Royal Society  of Chemistry
T2  - New Journal of Chemistry
T1  - Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene
VL  - 45
IS  - 11
SP  - 5060
EP  - 5074
DO  - 10.1039/d1nj00207d
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
abstract = "Aromaticity–antiaromaticity switch upon singlet–triplet transition of some biologically and synthetically
important monoheterocycles (heteroatom = N, O, Si, P, and S) derived from benzene, naphthalene and
anthracene was studied by employing energetic, magnetic and structural aromaticity criteria, at the
density functional theory (DFT) level. The relationship between spin density distribution, (anti)aromaticity
and singlet–triplet energy gaps, in the studied molecules, was found. In general, spin delocalization
results in antiaromaticity, spin density localization to one ring in bi- and tricycles localizes antiaromaticity
and spin localization on a heteroatom reduces global and local antiaromaticity. The latter reaches
nonaromaticity in the case of silicon atoms which have larger orbitals and show more tendency to
accept unpaired electrons. Spin density localization in bi- and tricycles allows benzene subunit(s) to
develop local aromaticity, which, when combined with nonaromatic silacycle and weak global
antiaromaticity, results in overall triplet state weak aromaticity. The singlet–triplet energy gaps decrease
with a decrease in the triplet state antiaromaticity and are the lowest for silicon-containing compounds.",
publisher = "Royal Society  of Chemistry",
journal = "New Journal of Chemistry",
title = "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene",
volume = "45",
number = "11",
pages = "5060-5074",
doi = "10.1039/d1nj00207d"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2021). Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene. in New Journal of Chemistry
Royal Society  of Chemistry., 45(11), 5060-5074.
https://doi.org/10.1039/d1nj00207d

Baranac-Stojanović M, Stojanović M, Aleksić J. Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene. in New Journal of Chemistry. 2021;45(11):5060-5074.
doi:10.1039/d1nj00207d .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene" in New Journal of Chemistry, 45, no. 11 (2021):5060-5074,
https://doi.org/10.1039/d1nj00207d . .

TY  - DATA
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4484
AB  - Figure S1. Correlation of B3LYP and PBE0, CAM-B3LYP, M062X and MP2 bond lengths for all monocycles studied. Figure S2. Correlations between aromaticity indices calculated for monocycles. Tables S1-S4. Comparison of aromaticity indices calculated with different methods. Figures S3-S28. ACID plots of studied compounds. S4 Absolute energies and x, y, z coordinates of optimized structures. S18
PB  - Royal Society  of Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4484
ER  - 

@misc{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2021",
abstract = "Figure S1. Correlation of B3LYP and PBE0, CAM-B3LYP, M062X and MP2 bond lengths for all monocycles studied. Figure S2. Correlations between aromaticity indices calculated for monocycles. Tables S1-S4. Comparison of aromaticity indices calculated with different methods. Figures S3-S28. ACID plots of studied compounds. S4 Absolute energies and x, y, z coordinates of optimized structures. S18",
publisher = "Royal Society  of Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4484"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2021). Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene". in New Journal of Chemistry
Royal Society  of Chemistry..
https://hdl.handle.net/21.15107/rcub_cer_4484

Baranac-Stojanović M, Stojanović M, Aleksić J. Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene". in New Journal of Chemistry. 2021;.
https://hdl.handle.net/21.15107/rcub_cer_4484 .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Supplementary information for: "Triplet state (anti)aromaticity of some monoheterocyclic analogues of benzene, naphthalene and anthracene"" in New Journal of Chemistry (2021),
https://hdl.handle.net/21.15107/rcub_cer_4484 .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2451
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry-An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3135
AB  - We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistry-An Asian Journal
T1  - Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
VL  - 13
IS  - 14
SP  - 1811
EP  - 1835
DO  - 10.1002/asia.201800645
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2018",
abstract = "We present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistry-An Asian Journal",
title = "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes",
volume = "13",
number = "14",
pages = "1811-1835",
doi = "10.1002/asia.201800645"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2018). Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal
Wiley-V C H Verlag Gmbh, Weinheim., 13(14), 1811-1835.
https://doi.org/10.1002/asia.201800645

Aleksić J, Stojanović M, Baranac-Stojanović M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. in Chemistry-An Asian Journal. 2018;13(14):1811-1835.
doi:10.1002/asia.201800645 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes" in Chemistry-An Asian Journal, 13, no. 14 (2018):1811-1835,
https://doi.org/10.1002/asia.201800645 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2264
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2969
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}

Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b

Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .

Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1628
AB  - The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - The effect of steric repulsion on the torsional potential of n-butane: a theoretical study
VL  - 71
IS  - 32
SP  - 5119
EP  - 5123
DO  - 10.1016/j.tet.2015.06.002
ER  - 

@article{
author = "Stojanović, Milovan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2015",
abstract = "The origin of the rotational barriers in n-butane and gauche conformational energy, the prototypes of steric repulsion, has been re-examined by using energy decomposition analysis. The Pauli repulsion was found to be an important factor, but not the source of the barriers and gauche/anti energy difference. Rather, it should be considered as a driving force for structural changes accompanying the rotation. The repulsion (steric) energy partly transfers into the deformation energy of ethyl fragments and also affects a decrease in electrostatic, orbital and dispersion interactions by inducing the structural changes, particularly the central CC bond lengthening, while it becomes less destabilizing during the anti-butane rotation.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study",
volume = "71",
number = "32",
pages = "5119-5123",
doi = "10.1016/j.tet.2015.06.002"
}

Stojanović, M., Aleksić, J.,& Baranac-Stojanović, M.. (2015). The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 71(32), 5119-5123.
https://doi.org/10.1016/j.tet.2015.06.002

Stojanović M, Aleksić J, Baranac-Stojanović M. The effect of steric repulsion on the torsional potential of n-butane: a theoretical study. in Tetrahedron. 2015;71(32):5119-5123.
doi:10.1016/j.tet.2015.06.002 .

Stojanović, Milovan, Aleksić, Jovana, Baranac-Stojanović, Marija, "The effect of steric repulsion on the torsional potential of n-butane: a theoretical study" in Tetrahedron, 71, no. 32 (2015):5119-5123,
https://doi.org/10.1016/j.tet.2015.06.002 . .

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1775
AB  - 2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair -> O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane
VL  - 5
IS  - 29
SP  - 22980
EP  - 22995
DO  - 10.1039/c5ra01164g
ER  - 

@article{
author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan",
year = "2015",
abstract = "2-Haloethanol and 2-haloethylamine (halogen = F, Cl) prefer gauche conformation. This preference is significantly increased upon protonation. Commonly used explanations are based on intramolecular hydrogen bonding and hyperconjugation. 1,2-Difluoroethane prefers gauche conformation, too, while gaseous 1-chloro-2-fluoroethane is more stable as the anti conformer. The origin of these conformational preferences has been investigated by a quantitative partitioning of the gauche/anti energy difference into contributions from electrostatic, orbital, dispersion and Pauli interactions, and structural changes accompanying the rotation. The results show that, with two exceptions, the most important contributor to the gauche preference is electrostatic attraction, which is larger in gauche forms relative to the anti ones. Next come orbital interactions, while dispersion forces provide the smallest stabilizing energy. These energy components override destabilizing Pauli interactions and energetically costly structural changes. All gauche preferences also benefit from stereoelectronic effects, except in protonated 2-chloroethanol which, instead, shows a significant Cl lone pair -> O-H antibond mixing, associated with hydrogen bonding. The increase in the Pauli repulsion upon anti to gauche isomerization is more pronounced for fluorine than for chlorine derivatives. Thus, the smaller gauche effect in chloro-compounds and the anti preference in 1-chloro-2-fluoroethane have their origin in the decrease in electrostatic and orbital stabilizing interactions, a drop in the former being more pronounced.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane",
volume = "5",
number = "29",
pages = "22980-22995",
doi = "10.1039/c5ra01164g"
}

Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M.. (2015). Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(29), 22980-22995.
https://doi.org/10.1039/c5ra01164g

Baranac-Stojanović M, Aleksić J, Stojanović M. Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane. in RSC Advances. 2015;5(29):22980-22995.
doi:10.1039/c5ra01164g .

Baranac-Stojanović, Marija, Aleksić, Jovana, Stojanović, Milovan, "Energy decomposition analysis of gauche preference in 2-haloethanol, 2-haloethylamine (halogen = F, Cl), their protonated forms and anti preference in 1-chloro-2-fluoroethane" in RSC Advances, 5, no. 29 (2015):22980-22995,
https://doi.org/10.1039/c5ra01164g . .

TY  - JOUR
AU  - Aleksić, Jovana
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1814
AB  - The well-known gauche preference in FCCX systems, where X is an electronegative element from Period 2, is widely exploited in synthetic, medicinal, and material chemistry. It is rationalized on the basis of sigma(C-H)->sigma*(C-F) hyperconjugation and electrostatic interactions. The recent report (Thiehoff, C.; et al. Chem. Sci. 2015, 6, 3565) showed that the fluorine gauche effect can extend to Period 3 elements, such as sulfur. The aim of the present work is to disclose factors governing conformational behavior of FCCS containing systems. We examine conformational preferences in seven classes of compounds by ab initio and DFT calculations and rationalize the results by quantitatively decomposing the anti/gauche isomerization energy into contributions from electrostatic, orbital, dispersion, and Pauli interactions, and energy spent on structural changes. The results show that the fluorine/sulfur gauche effect is primarily electrostatic (63-75%), while all orbital interactions contribute 22-41% to stabilizing interactions. Stereoelectronic effects, involved in orbital interactions, also play a role in gauche conformer stabilization.
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion
VL  - 80
IS  - 20
SP  - 10197
EP  - 10207
DO  - 10.1021/acs.joc.5b01779
ER  - 

@article{
author = "Aleksić, Jovana and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2015",
abstract = "The well-known gauche preference in FCCX systems, where X is an electronegative element from Period 2, is widely exploited in synthetic, medicinal, and material chemistry. It is rationalized on the basis of sigma(C-H)->sigma*(C-F) hyperconjugation and electrostatic interactions. The recent report (Thiehoff, C.; et al. Chem. Sci. 2015, 6, 3565) showed that the fluorine gauche effect can extend to Period 3 elements, such as sulfur. The aim of the present work is to disclose factors governing conformational behavior of FCCS containing systems. We examine conformational preferences in seven classes of compounds by ab initio and DFT calculations and rationalize the results by quantitatively decomposing the anti/gauche isomerization energy into contributions from electrostatic, orbital, dispersion, and Pauli interactions, and energy spent on structural changes. The results show that the fluorine/sulfur gauche effect is primarily electrostatic (63-75%), while all orbital interactions contribute 22-41% to stabilizing interactions. Stereoelectronic effects, involved in orbital interactions, also play a role in gauche conformer stabilization.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion",
volume = "80",
number = "20",
pages = "10197-10207",
doi = "10.1021/acs.joc.5b01779"
}

Aleksić, J., Stojanović, M.,& Baranac-Stojanović, M.. (2015). Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. in Journal of Organic Chemistry
American Chemical Society (ACS)., 80(20), 10197-10207.
https://doi.org/10.1021/acs.joc.5b01779

Aleksić J, Stojanović M, Baranac-Stojanović M. Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion. in Journal of Organic Chemistry. 2015;80(20):10197-10207.
doi:10.1021/acs.joc.5b01779 .

Aleksić, Jovana, Stojanović, Milovan, Baranac-Stojanović, Marija, "Origin of Fluorine/Sulfur Gauche Effect of beta-Fluorinated Thiol, Sulfoxide, Sulfone, and Thionium Ion" in Journal of Organic Chemistry, 80, no. 20 (2015):10197-10207,
https://doi.org/10.1021/acs.joc.5b01779 . .

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
AU  - Aleksić, Jovana
AU  - Baranac-Stojanović, Marija
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1565
AB  - 4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Current Organic Chemistry
T1  - 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity
VL  - 18
IS  - 9
SP  - 1108
EP  - 1148
DO  - 10.2174/138527281809140624120436
ER  - 

@article{
author = "Stojanović, Milovan and Džambaski, Zdravko and Bondžić, Bojan and Aleksić, Jovana and Baranac-Stojanović, Marija",
year = "2014",
abstract = "4-Oxothiazolidine core, owing to the wide range of pharmacological activities exhibited by its derivatives, has been recognized as an important structural motif in biologically active compounds. A subclass constitutes 4-oxothiazolidines with an exocyclic C=C double bond at the C(2)-position. Some of these derivatives are registered as active substances for the treatment of various diseases, such as Ralitoline, an antiepileptic, Etozolin, a diuretic, and Piprozolin, a choleretic. The exocyclic C=C double bond in these compounds contains one or two electron-accepting groups at its other end, so that they also belong to the class of the so-called push-pull alkenes. In the case of the nitrogen-unsubstituted molecules, the enamino tautomeric form with the exocyclic double bond is stabilized by the extended electron delocalization arising from the push-pull effect. In the absence of push-pull effect, the imino form would dominate. Therefore, these compounds exhibit properties characteristic for both 4-oxothiazolidine ring and push-pull alkenes. They are also proved to be useful synthetic interamediates for the formation of various mono- and polyheterocycles. The importance of 4-oxothiazolidine derivatives is witnessed by several review articles, the latest published in 2012, mainly dealing with the chemistry and biological activity of various 2-imino, 2-oxo, 2-thioxo and 2-alkyl(aryl)-substituted compounds. The lack of a comprehensive review on 2-alkylidene-4-oxothiazolidines has prompted us to collect the literature covering their synthesis, structure, reactivity and biological activity. Derivatives with two exocyclic C=C double bonds are included, too.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Current Organic Chemistry",
title = "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity",
volume = "18",
number = "9",
pages = "1108-1148",
doi = "10.2174/138527281809140624120436"
}

Stojanović, M., Džambaski, Z., Bondžić, B., Aleksić, J.,& Baranac-Stojanović, M.. (2014). 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity. in Current Organic Chemistry
Bentham Science Publ Ltd, Sharjah., 18(9), 1108-1148.
https://doi.org/10.2174/138527281809140624120436

Stojanović M, Džambaski Z, Bondžić B, Aleksić J, Baranac-Stojanović M. 4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity. in Current Organic Chemistry. 2014;18(9):1108-1148.
doi:10.2174/138527281809140624120436 .

Stojanović, Milovan, Džambaski, Zdravko, Bondžić, Bojan, Aleksić, Jovana, Baranac-Stojanović, Marija, "4-Oxothiazolidines with Exocyclic C=C Double Bond(s): Synthesis, Structure, Reactions and Biological Activity" in Current Organic Chemistry, 18, no. 9 (2014):1108-1148,
https://doi.org/10.2174/138527281809140624120436 . .

TY  - THES
AU  - Aleksić, Jovana
PY  - 2013
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=1207
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:8119/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=45194511
UR  - http://nardus.mpn.gov.rs/123456789/3501
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2515
AB  - Halofilne reakcije predstavljaju vrstu nukleofilnih supstitucionih reakcija dokojih dolazi kada nukleofil reaguje sa atomom halogena, nakon ega se oslobaakarbanjon kao odlazea grupa. To su relativno rijetke reakcije koje se dešavaju ukolikoje klasina nukleofilna supstitucija (karbofilna reakcija) iz nekog razloga otežana i/ilikada je karbanjon stabilizovan prisustvom elektron-privlanih supstituenata.Cilj ovog rada je bio da se ispitaju halofilne reakcije i njihova sintetikaprimena na dva sistema: 2-alkiliden-4-oksotiazolidin vinil-bromidima i ,-dibrom-2-metoksiacetofenonu. Znaaj ovih reakcija u sluaju ispitivanih N-nesupstituisanihtiazolidinskih jedinjenja je u dobijanju novih, potencijalno biološki aktivnih C-5funkcionalizovanih derivata. Ovakvi derivati se ne mogu dobiti direktno reakcionomsekvencom C-5 bromovanje/nukleofilna supstitucija, jer je bromovanje Nnesupstituisanih2-alkiliden-4-oksotiazolidina visoko regioselektivno i kao proizvodi sedobijaju iskljuivo vinil-bromidi. Znaaj prouavanja ovakvih reakcija u sluaju a,a-dibrom-2-metoksiacetofenona proistie iz injenice da se selektivno a-monobromovanje metil-ketona esto teško postiže, a praeno je stvaranjem a,a-dibromderivatakao sporednih, a ponekad i kao glavnih proizvoda. Mogua kaskadnahalofilna/karbofilna reakcija bi omoguila korišenje dibrom-derivata kao sintetikihekvivalenta monobromida, ime bi se izbegla dodatna faza selektivnog debromovanjaradi dobijanja monobrom-derivata, kao znaajnih sintetikih intermedijera. Razliitineutralni i anjonski nukleofili su uestvovali u halofilnoj reakciji sa tiazolidinskim vinilbromidimadajui tri vrste proizvoda: i) proizvod reduktivnog debromovanja, ii)proizvod supstitucije broma i iii) C-5 funkcionalizovan proizvod. Takoe je pokazanoda se ,-dibrom-2-metoksiacetofenon može upotrebiti kao sintetiki ekvivalent a-monobromacetofenona.Pored navedenih halofilnih reakcija, u ovom radu ispitivana je i mogunostizvoenja Suzuki-Miyaura reakcije na vinil-bromidima, kao i mogua regioselektivnostove reakcije na N-supstituisanom tribrompirazolu, a u cilju dobijanja novih,potencijalno biološki aktivnih jedinjenja. Suzuki-Miyaura reakcija sa derivatimaarilbornih kiselina izvedena na vinil-bromidima nije dala oekivani rezultat, ali jeuspešno izvedena sa N-supstituisanim tribrompirazolima uz visoku regioselektivnost,pri emu su sintetisani 5-supstituisani 3,4-dibrompirazoli sa 1,1 ekvivalentom arilbornihkiselina, 3,5-disupstituisani 4-brompirazoli sa 2,2 ekvivalenta arilbornih kiselina i 3,4,5-trisupstituisani derivati sa 3,5 ekvivalenata arilbornih kiselina.S obzirom da ispitivani tiazolidini spadaju u grupu push-pull alkena, kod kojihelektronska delokalizacija izmeu donorskih i akceptorskih grupa na dvostrukoj veziima znaajan uticaj na njihove osobine i hemijsku reaktivnost, uraena je ikvantifikacija push-pull efekta dvostruke veze.
AB  - Halophilic reactions are nucleophilic substitution reactions in whichnucleophile attacks halogen atom with the carbanion acting as a leaving group. They arerelatively rare and usually take place if the classic nucleophilic substitution (carbophilicreaction) is made difficult, and/or if the resulting carbanion is stabilized by electronwithdrawingsubstituents.The aim of the present work was to study halophilic reactions and theirsynthetic application on two systems: 2-alkylidene-4-oxothiazolidines vinyl bromidesand ,-dibromo-2-methoxyacetophenone. The significance of the studied reactions inthe case of N-unsubstituited thiazolidine compounds would be the synthesis of novel,potentially biologically active C-5 substituted derivatives. These derivatives areimpossible to obtain directly by the C-5 bromination/SNC substitution reactionsequence, since bromination of N-unsubstituited 2-alkylidene-4-oxothiazolidines ishighly regioselective, resulting in the formation of vinyl bromides as sole products.Significance of the studied reactions in the case of ,-dibromo-2-methoxyacetophenone arises from the fact that selective a-monobromination of methylketones of often difficult to achieve. ,-Dibromo derivatives can be formed as sideproducts, or even as major ones. A possible cascade halophilic/carbophilic reactionwould allow the use of dibromo derivatives as synthetic equivalents of monobromocompounds, thus avoiding the additional step, selective debromination, necessary toobtain synthetically useful monobromo derivatives. Various neutral and anionicnucleophiles underwent a halophilic reaction with thiazolidine vinyl bromides yieldingthree types of products: i) products of reductive debromination, ii) bromine susbtitutionproducts and iii) C-5 functionalized products. It has also been shown that ,-dibromo-2-methoxyacetophenone can be used as synthetic equivalent of a-monobromoacetophenone.Apart from the mentioned halophilic reactions, a possibility of Suzuki-Miyaurareaction to take place with the vinyl bromides was investigated, along with the possibleregioselectivity of the same reaction applied to N-substituted tribromopyrazoles, all withthe aim to obtaine new, potentially biologically active compounds. Suzuki-Miyaurareaction of vinyl bromides with aryl boronic acid did not give the expectedtetrasubstituted alkenes. On the contrary, Suzuki-Miyaura reaction performed with theN-substituted tribromopyrazoles showed high regioselectivity yielding 5-substituted3,4-dibromopyrazoles with 1.1 equivalent of aryl boronic acids, 3,5-disubstituted 4-bromo derivatives with 2.2 equivalents of aryl boronic acids and 3,4,5-trisubstitutedderivatives with 3.5 equivalents of aryl boronic acids.Studied thiazolidine derivatives belong to the class of the so-called push-pullalkenes in which electronic delocalization beween donor and acceptor groups attachedat the C=C double bond highly influences their properties and chemical reactivity. Forthis reason, one aim of the present work was also to quantify this push-pull effect of thestudied compounds.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - 4-oksotiazolidin-2-alkiliden vinil-bromidi i α, α-dibrom-2-metoksiacetofenon : prekursori u sintetički korisnim transformacijama iniciranim retkim halofilnim napadom nukleofila
T1  - 4-oxothiazolidine-2-alkylidene vinyl bromides and a,a-dibromo-2-methoxyacetophenone: precursors in synthetically useful transformations initiated by the rare halophilic attack of nucleophiles
UR  - https://hdl.handle.net/21.15107/rcub_nardus_3501
ER  - 

@phdthesis{
author = "Aleksić, Jovana",
year = "2013",
abstract = "Halofilne reakcije predstavljaju vrstu nukleofilnih supstitucionih reakcija dokojih dolazi kada nukleofil reaguje sa atomom halogena, nakon ega se oslobaakarbanjon kao odlazea grupa. To su relativno rijetke reakcije koje se dešavaju ukolikoje klasina nukleofilna supstitucija (karbofilna reakcija) iz nekog razloga otežana i/ilikada je karbanjon stabilizovan prisustvom elektron-privlanih supstituenata.Cilj ovog rada je bio da se ispitaju halofilne reakcije i njihova sintetikaprimena na dva sistema: 2-alkiliden-4-oksotiazolidin vinil-bromidima i ,-dibrom-2-metoksiacetofenonu. Znaaj ovih reakcija u sluaju ispitivanih N-nesupstituisanihtiazolidinskih jedinjenja je u dobijanju novih, potencijalno biološki aktivnih C-5funkcionalizovanih derivata. Ovakvi derivati se ne mogu dobiti direktno reakcionomsekvencom C-5 bromovanje/nukleofilna supstitucija, jer je bromovanje Nnesupstituisanih2-alkiliden-4-oksotiazolidina visoko regioselektivno i kao proizvodi sedobijaju iskljuivo vinil-bromidi. Znaaj prouavanja ovakvih reakcija u sluaju a,a-dibrom-2-metoksiacetofenona proistie iz injenice da se selektivno a-monobromovanje metil-ketona esto teško postiže, a praeno je stvaranjem a,a-dibromderivatakao sporednih, a ponekad i kao glavnih proizvoda. Mogua kaskadnahalofilna/karbofilna reakcija bi omoguila korišenje dibrom-derivata kao sintetikihekvivalenta monobromida, ime bi se izbegla dodatna faza selektivnog debromovanjaradi dobijanja monobrom-derivata, kao znaajnih sintetikih intermedijera. Razliitineutralni i anjonski nukleofili su uestvovali u halofilnoj reakciji sa tiazolidinskim vinilbromidimadajui tri vrste proizvoda: i) proizvod reduktivnog debromovanja, ii)proizvod supstitucije broma i iii) C-5 funkcionalizovan proizvod. Takoe je pokazanoda se ,-dibrom-2-metoksiacetofenon može upotrebiti kao sintetiki ekvivalent a-monobromacetofenona.Pored navedenih halofilnih reakcija, u ovom radu ispitivana je i mogunostizvoenja Suzuki-Miyaura reakcije na vinil-bromidima, kao i mogua regioselektivnostove reakcije na N-supstituisanom tribrompirazolu, a u cilju dobijanja novih,potencijalno biološki aktivnih jedinjenja. Suzuki-Miyaura reakcija sa derivatimaarilbornih kiselina izvedena na vinil-bromidima nije dala oekivani rezultat, ali jeuspešno izvedena sa N-supstituisanim tribrompirazolima uz visoku regioselektivnost,pri emu su sintetisani 5-supstituisani 3,4-dibrompirazoli sa 1,1 ekvivalentom arilbornihkiselina, 3,5-disupstituisani 4-brompirazoli sa 2,2 ekvivalenta arilbornih kiselina i 3,4,5-trisupstituisani derivati sa 3,5 ekvivalenata arilbornih kiselina.S obzirom da ispitivani tiazolidini spadaju u grupu push-pull alkena, kod kojihelektronska delokalizacija izmeu donorskih i akceptorskih grupa na dvostrukoj veziima znaajan uticaj na njihove osobine i hemijsku reaktivnost, uraena je ikvantifikacija push-pull efekta dvostruke veze., Halophilic reactions are nucleophilic substitution reactions in whichnucleophile attacks halogen atom with the carbanion acting as a leaving group. They arerelatively rare and usually take place if the classic nucleophilic substitution (carbophilicreaction) is made difficult, and/or if the resulting carbanion is stabilized by electronwithdrawingsubstituents.The aim of the present work was to study halophilic reactions and theirsynthetic application on two systems: 2-alkylidene-4-oxothiazolidines vinyl bromidesand ,-dibromo-2-methoxyacetophenone. The significance of the studied reactions inthe case of N-unsubstituited thiazolidine compounds would be the synthesis of novel,potentially biologically active C-5 substituted derivatives. These derivatives areimpossible to obtain directly by the C-5 bromination/SNC substitution reactionsequence, since bromination of N-unsubstituited 2-alkylidene-4-oxothiazolidines ishighly regioselective, resulting in the formation of vinyl bromides as sole products.Significance of the studied reactions in the case of ,-dibromo-2-methoxyacetophenone arises from the fact that selective a-monobromination of methylketones of often difficult to achieve. ,-Dibromo derivatives can be formed as sideproducts, or even as major ones. A possible cascade halophilic/carbophilic reactionwould allow the use of dibromo derivatives as synthetic equivalents of monobromocompounds, thus avoiding the additional step, selective debromination, necessary toobtain synthetically useful monobromo derivatives. Various neutral and anionicnucleophiles underwent a halophilic reaction with thiazolidine vinyl bromides yieldingthree types of products: i) products of reductive debromination, ii) bromine susbtitutionproducts and iii) C-5 functionalized products. It has also been shown that ,-dibromo-2-methoxyacetophenone can be used as synthetic equivalent of a-monobromoacetophenone.Apart from the mentioned halophilic reactions, a possibility of Suzuki-Miyaurareaction to take place with the vinyl bromides was investigated, along with the possibleregioselectivity of the same reaction applied to N-substituted tribromopyrazoles, all withthe aim to obtaine new, potentially biologically active compounds. Suzuki-Miyaurareaction of vinyl bromides with aryl boronic acid did not give the expectedtetrasubstituted alkenes. On the contrary, Suzuki-Miyaura reaction performed with theN-substituted tribromopyrazoles showed high regioselectivity yielding 5-substituted3,4-dibromopyrazoles with 1.1 equivalent of aryl boronic acids, 3,5-disubstituted 4-bromo derivatives with 2.2 equivalents of aryl boronic acids and 3,4,5-trisubstitutedderivatives with 3.5 equivalents of aryl boronic acids.Studied thiazolidine derivatives belong to the class of the so-called push-pullalkenes in which electronic delocalization beween donor and acceptor groups attachedat the C=C double bond highly influences their properties and chemical reactivity. Forthis reason, one aim of the present work was also to quantify this push-pull effect of thestudied compounds.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "4-oksotiazolidin-2-alkiliden vinil-bromidi i α, α-dibrom-2-metoksiacetofenon : prekursori u sintetički korisnim transformacijama iniciranim retkim halofilnim napadom nukleofila, 4-oxothiazolidine-2-alkylidene vinyl bromides and a,a-dibromo-2-methoxyacetophenone: precursors in synthetically useful transformations initiated by the rare halophilic attack of nucleophiles",
url = "https://hdl.handle.net/21.15107/rcub_nardus_3501"
}

Aleksić, J.. (2013). 4-oksotiazolidin-2-alkiliden vinil-bromidi i α, α-dibrom-2-metoksiacetofenon : prekursori u sintetički korisnim transformacijama iniciranim retkim halofilnim napadom nukleofila. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_3501

Aleksić J. 4-oksotiazolidin-2-alkiliden vinil-bromidi i α, α-dibrom-2-metoksiacetofenon : prekursori u sintetički korisnim transformacijama iniciranim retkim halofilnim napadom nukleofila. in Универзитет у Београду. 2013;.
https://hdl.handle.net/21.15107/rcub_nardus_3501 .

Aleksić, Jovana, "4-oksotiazolidin-2-alkiliden vinil-bromidi i α, α-dibrom-2-metoksiacetofenon : prekursori u sintetički korisnim transformacijama iniciranim retkim halofilnim napadom nukleofila" in Универзитет у Београду (2013),
https://hdl.handle.net/21.15107/rcub_nardus_3501 .