Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions
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/...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2011-03-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.rs/JSCS/Vol76/No3/01_4812_4120.pdf |
| _version_ | 1818823799985930240 |
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| author | ZDRAVKO DŽAMBASKI MILOVAN STOJANOVIĆ MARIJA BARANAC-STOJANOVIĆ DRAGICA M. MINIĆ RADE MARKOVIĆ |
| author_facet | ZDRAVKO DŽAMBASKI MILOVAN STOJANOVIĆ MARIJA BARANAC-STOJANOVIĆ DRAGICA M. MINIĆ RADE MARKOVIĆ |
| author_sort | ZDRAVKO DŽAMBASKI |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-18T23:45:44Z |
| format | Article |
| id | doaj.art-2c94b11862684522997cbfcd45dfa724 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-12-18T23:45:44Z |
| publishDate | 2011-03-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-2c94b11862684522997cbfcd45dfa7242022-12-21T20:47:14ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392011-03-01763317328Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactionsZDRAVKO DŽAMBASKIMILOVAN STOJANOVIĆMARIJA BARANAC-STOJANOVIĆDRAGICA M. MINIĆRADE MARKOVIĆConfigurational 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.http://www.shd.org.rs/JSCS/Vol76/No3/01_4812_4120.pdf4-thiazolidinonessolid-state isomerisationnon-covalent interactionsdynamic 1H-NMR spectroscopy |
| spellingShingle | ZDRAVKO DŽAMBASKI MILOVAN STOJANOVIĆ MARIJA BARANAC-STOJANOVIĆ DRAGICA M. MINIĆ RADE MARKOVIĆ Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions Journal of the Serbian Chemical Society 4-thiazolidinones solid-state isomerisation non-covalent interactions dynamic 1H-NMR spectroscopy |
| title | Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions |
| title_full | Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions |
| title_fullStr | Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions |
| title_full_unstemmed | Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions |
| title_short | Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions |
| title_sort | thermal solid state z e isomerization of 2 alkylidene 4 oxothiazolidines effects of non covalent interactions |
| topic | 4-thiazolidinones solid-state isomerisation non-covalent interactions dynamic 1H-NMR spectroscopy |
| url | http://www.shd.org.rs/JSCS/Vol76/No3/01_4812_4120.pdf |
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