Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions
Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija
2011
Authors
Džambaski, ZdravkoStojanović, Milovan
Baranac-Stojanović, Marija
Minić, Dragica M.
Marković, Rade
Article (Published version)
Metadata
Show full item recordAbstract
Configurational isomerization of stereo-defined 5-substituted and unsubstituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by 1H-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolecular hydrogen bonding and directional non-bonded 1,5-type S∙∙∙O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z→E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.
Konfiguraciona izomerizacija stereodefinisanih 5-supstituisanih i nesupstituisanih 2-alkiliden-4-oksotiazolidina 1 u čvrstom stanju, pri čemu se stvara Z/E smesa u različitim odnosima, proučavana je pomoću 1H-NMR spektroskopije, rendgenske kristalografije praha i diferencijalne skenirajuće kalorimetrije (DSK). Odnos Z/E izomera može se objasniti u kontekstu nekovalentnih interakcija, koje obuhvataju intermolekulsko i intramolekulsko vodonično vezivanje i usmerene nevezivne S∙∙∙O interakcije 1,5-tipa. Rendgenska kristalografija praha odabranog kristalnog (Z)-4-oksotiazolidinskog supstrata, potvrdila je transformaciju u amorfno stanje u toku ireverzibilnog Z→E procesa. Postavljena je korelacija između prethodnih rezultata koji se odnose na Z/E izomerizaciju u rastvoru, i sada, u čvrstom stanju.
Keywords:
4-thiazolidinones / solid-state isomerisation / non-covalent interactions / dynamic 1H-NMR spectroscopySource:
Journal of the Serbian Chemical Society, 2011, 76, 3, 317-328Publisher:
- Serbian Chemical Soc, Belgrade
Funding / projects:
- Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-MESTD-MPN2006-2010-142007)
DOI: 10.2298/JSC100607038D
ISSN: 0352-5139
WoS: 000289270000001
Scopus: 2-s2.0-79953153021
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IHTMTY - JOUR AU - Džambaski, Zdravko AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija AU - Minić, Dragica M. AU - Marković, Rade PY - 2011 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/910 AB - Configurational isomerization of stereo-defined 5-substituted and unsubstituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by 1H-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolecular hydrogen bonding and directional non-bonded 1,5-type S∙∙∙O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z→E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established. AB - Konfiguraciona izomerizacija stereodefinisanih 5-supstituisanih i nesupstituisanih 2-alkiliden-4-oksotiazolidina 1 u čvrstom stanju, pri čemu se stvara Z/E smesa u različitim odnosima, proučavana je pomoću 1H-NMR spektroskopije, rendgenske kristalografije praha i diferencijalne skenirajuće kalorimetrije (DSK). Odnos Z/E izomera može se objasniti u kontekstu nekovalentnih interakcija, koje obuhvataju intermolekulsko i intramolekulsko vodonično vezivanje i usmerene nevezivne S∙∙∙O interakcije 1,5-tipa. Rendgenska kristalografija praha odabranog kristalnog (Z)-4-oksotiazolidinskog supstrata, potvrdila je transformaciju u amorfno stanje u toku ireverzibilnog Z→E procesa. Postavljena je korelacija između prethodnih rezultata koji se odnose na Z/E izomerizaciju u rastvoru, i sada, u čvrstom stanju. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions T1 - Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija VL - 76 IS - 3 SP - 317 EP - 328 DO - 10.2298/JSC100607038D ER -
@article{ author = "Džambaski, Zdravko and Stojanović, Milovan and Baranac-Stojanović, Marija and Minić, Dragica M. and Marković, Rade", year = "2011", abstract = "Configurational isomerization of stereo-defined 5-substituted and unsubstituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by 1H-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolecular hydrogen bonding and directional non-bonded 1,5-type S∙∙∙O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z→E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established., Konfiguraciona izomerizacija stereodefinisanih 5-supstituisanih i nesupstituisanih 2-alkiliden-4-oksotiazolidina 1 u čvrstom stanju, pri čemu se stvara Z/E smesa u različitim odnosima, proučavana je pomoću 1H-NMR spektroskopije, rendgenske kristalografije praha i diferencijalne skenirajuće kalorimetrije (DSK). Odnos Z/E izomera može se objasniti u kontekstu nekovalentnih interakcija, koje obuhvataju intermolekulsko i intramolekulsko vodonično vezivanje i usmerene nevezivne S∙∙∙O interakcije 1,5-tipa. Rendgenska kristalografija praha odabranog kristalnog (Z)-4-oksotiazolidinskog supstrata, potvrdila je transformaciju u amorfno stanje u toku ireverzibilnog Z→E procesa. Postavljena je korelacija između prethodnih rezultata koji se odnose na Z/E izomerizaciju u rastvoru, i sada, u čvrstom stanju.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions, Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija", volume = "76", number = "3", pages = "317-328", doi = "10.2298/JSC100607038D" }
Džambaski, Z., Stojanović, M., Baranac-Stojanović, M., Minić, D. M.,& Marković, R.. (2011). Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 76(3), 317-328. https://doi.org/10.2298/JSC100607038D
Džambaski Z, Stojanović M, Baranac-Stojanović M, Minić DM, Marković R. Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions. in Journal of the Serbian Chemical Society. 2011;76(3):317-328. doi:10.2298/JSC100607038D .
Džambaski, Zdravko, Stojanović, Milovan, Baranac-Stojanović, Marija, Minić, Dragica M., Marković, Rade, "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions" in Journal of the Serbian Chemical Society, 76, no. 3 (2011):317-328, https://doi.org/10.2298/JSC100607038D . .