Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions-Reference-Cited by-同舟云学术

Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions

Published:2011 Issue:3 Volume:76 Page:317-328
ISSN:0352-5139
Container-title:Journal of the Serbian Chemical Society
language:en
Short-container-title:JSCS

Author:

Dzambaski Zdravko¹,Stojanovic Milovan¹,Baranac-Stojanovic Marija²^ORCID,Minic Dragica³^ORCID,Markovic Rade²

Affiliation:

1. Centre for Chemistry, ICTM, Belgrade

2. Centre for Chemistry, ICTM, Belgrade + Faculty of Chemistry, Belgrade

3. Centre for Chemistry, ICTM, Belgrade + Faculty of Physical Chemistry, Belgrade

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 substrates, 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.

Publisher

National Library of Serbia

Subject

General Chemistry

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