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.
TY - JOUR
AU - Džambaski, Zdravko
AU - Stojanović, Milovan
AU - Baranac-Stojanović, Marija
AU - Minić, Dragica M.
AU - Marković, Rade
PY - 2011
UR - http://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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/910",
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 DM, Marković R. Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija. Journal of the Serbian Chemical Society. 2011;76(3):317-328
Džambaski, Z., Stojanović, M., Baranac-Stojanović, M., Minić, D. M.,& Marković, R. (2011). Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija.
Journal of the Serbian Chemical SocietySerbian Chemical Soc, Belgrade., 76(3), 317-328.
https://doi.org/10.2298/JSC100607038D
Džambaski Zdravko, Stojanović Milovan, Baranac-Stojanović Marija, Minić Dragica M., Marković Rade, "Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija" 76, no. 3 (2011):317-328,
https://doi.org/10.2298/JSC100607038D .
