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in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues

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2017
vujovic2017accepted.pdf (1.630Mb)
Authors
Vujovic, Milena
Zlatar, Matija
Milčić, Miloš
Gruden, Maja
Article (Accepted Version)
,
Royal Society of Chemistry
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Abstract
A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects.
Source:
Physical Chemistry Chemical Physics, 2017, 19, 14, 9500-9508
Publisher:
  • Royal Soc Chemistry, Cambridge
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
Note:
  • This is the peer-reviewed version of the article: Vujovic, M.; Zlatar, M.; Milčić, M. K.; Gruden-Pavlović, M. In/out Isomerism of Cyclophanes: A Theoretical Account of 2,6,15-Trithia-(3(4,10))(7)Metacyclophane and (3(4,10))(7)Metacyclophane as Well as Their Halogen Substituted Analogues. Physical Chemistry Chemical Physics 2017, 19 (14), 9500–9508. https://doi.org/10.1039/c7cp00557a
  • http://cer.ihtm.bg.ac.rs/handle/123456789/2202

DOI: 10.1039/c7cp00557a

ISSN: 1463-9076

PubMed: 28338132

WoS: 000399164400018

Scopus: 2-s2.0-85019573956
[ Google Scholar ]
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2
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2903
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Vujovic, Milena
AU  - Zlatar, Matija
AU  - Milčić, Miloš
AU  - Gruden, Maja
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2903
AB  - A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects.
PB  - Royal Soc Chemistry, Cambridge
T2  - Physical Chemistry Chemical Physics
T1  - in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues
VL  - 19
IS  - 14
SP  - 9500
EP  - 9508
DO  - 10.1039/c7cp00557a
ER  - 
@article{
author = "Vujovic, Milena and Zlatar, Matija and Milčić, Miloš and Gruden, Maja",
year = "2017",
abstract = "A detailed theoretical investigation of cyclophanes with a divergent set of methods ranging from molecular mechanics through semiempirical to ab initio is presented. Cyclophanes have attracted interest over the years due to their unusual chemistry and increasing applications. There has been previous debate over the effects contributing to the greater stability of more-crowded in isomers of certain cyclophanes, and a higher strain in the out isomer was the prevailing explanation. Application of EDA-NOCV and SAPT analysis has enabled us to distinguish between different effects controlling isomer stability and determine the significance of all effects involved. Our results show that, although strain has a large significance, orbital stabilization within the molecule from the aromatic electron density is crucial. Furthermore, we analysed halogen-substituted cyclophanes in order to further understand these subtle effects.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Physical Chemistry Chemical Physics",
title = "in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues",
volume = "19",
number = "14",
pages = "9500-9508",
doi = "10.1039/c7cp00557a"
}
Vujovic, M., Zlatar, M., Milčić, M.,& Gruden, M.. (2017). in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues. in Physical Chemistry Chemical Physics
Royal Soc Chemistry, Cambridge., 19(14), 9500-9508.
https://doi.org/10.1039/c7cp00557a
Vujovic M, Zlatar M, Milčić M, Gruden M. in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues. in Physical Chemistry Chemical Physics. 2017;19(14):9500-9508.
doi:10.1039/c7cp00557a .
Vujovic, Milena, Zlatar, Matija, Milčić, Miloš, Gruden, Maja, "in/out Isomerism of cyclophanes: a theoretical account of 2,6,15-trithia-[3(4,10)][7]metacyclophane and [3(4,10)][7]metacyclophane as well as their halogen substituted analogues" in Physical Chemistry Chemical Physics, 19, no. 14 (2017):9500-9508,
https://doi.org/10.1039/c7cp00557a . .

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