Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: effects of non-covalent interactions
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 un-substituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by H-1-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 intramolccular hydrogen bonding and directional non-bonded 1,5-type S center dot center dot center dot O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z - gt E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.
Keywords:
4-thiazolidinones / solid-state isomerisation / non-covalent interactions / dynamic H-1-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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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Džambaski, Zdravko AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija AU - Minić, Dragica M. AU - Marković, Rade PY - 2011 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1331 AB - Configurational isomerization of stereo-defined 5-substituted and un-substituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by H-1-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 intramolccular hydrogen bonding and directional non-bonded 1,5-type S center dot center dot center dot O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z - gt E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established. 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 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 un-substituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by H-1-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 intramolccular hydrogen bonding and directional non-bonded 1,5-type S center dot center dot center dot O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z - gt E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.", 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", 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 . .