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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

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2011
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Authors
Džambaski, Zdravko
Stojanović, Milovan
Baranac-Stojanović, Marija
Minić, Dragica M.
Marković, Rade
Article (Published version)
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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.
Keywords:
4-thiazolidinones / solid-state isomerisation / non-covalent interactions / dynamic 1H-NMR spectroscopy
Source:
Journal of the Serbian Chemical Society, 2011, 76, 3, 317-328
Publisher:
  • Serbian Chemical Soc, Belgrade
Projects:
  • Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-142007)

DOI: 10.2298/JSC100607038D

ISSN: 0352-5139

WoS: 000289270000001

Scopus: 2-s2.0-79953153021
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/910
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