Proton tautomerism and stereoisomerism in 5-[(dimethylamino)methylidene]-4-[3/4-(trifluoromethylphenyl)amino]-1,3-thiazol-2(5H)-ones: synthesis, crystal structure and spectroscopic studies,Acta Crystallographica Section C

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Proton tautomerism and stereoisomerism in 5-[(dimethylamino)methylidene]-4-[3/4-(trifluoromethylphenyl)amino]-1,3-thiazol-2(5H)-ones: synthesis, crystal structure and spectroscopic studies
Acta Crystallographica Section C ( IF 0.7 ) Pub Date : 2023-10-24 , DOI: 10.1107/s2053229623009087
Andrii Pyrih ₁ , Andrzej Łapiński ₂ , Sylwia Zięba ₂ , Adam Mizera ₂ , Roman Lesyk ₃ , Andrzej K Gzella ₄ , Mariusz Jaskolski ₁

Affiliation

5-[(Dimethylamino)methylidene]-4-{[3-(trifluoromethyl)phenyl]amino}-1,3-thiazol-2(5H)-one and the [4-(trifluoromethyl)phenyl]amino derivative, both C₁₃H₁₂F₃N₃OS, with the trifluoromethyl group substituted at the arene ring at the meta and para positions, were synthesized to study the structural changes associated with proton tautomerism of the amidine system. The studied compounds were found to be in the amine tautomeric form in both the solid and the liquid (dimethyl sulfoxide solutions) phase. In both isomers, the [(trifluoromethyl)phenyl]amino residue assumes a synperiplanar conformation with respect to the thiazolone system, while the 5-[(dimethylamino)methylidene] residue adopts the Z configuration. Density functional theory (DFT) calculations correctly predicted that the synperiplanar arrangement is favoured in both isomers. In the crystal, the whole independent molecule of the para compound is disordered over two alternative positions, with occupancy factors of 0.926 (3) and 0.074 (3).

中文翻译：

5-[(二甲基氨基)亚甲基]-4-[3/4-(三氟甲基苯基)氨基]-1,3-噻唑-2(5H)-酮中的质子互变异构和立体异构：合成、晶体结构和光谱研究

5-[(二甲氨基)亚甲基]-4-{[3-(三氟甲基)苯基]氨基}-1,3-噻唑-2(5H ) -酮和[4-(三氟甲基)苯基]氨基衍生物合成了在间位和对位芳烃环上被三氟甲基取代的C ₁₃ H ₁₂ F ₃ N ₃ OS ，以研究与脒系统质子互变异构相关的结构变化。发现所研究的化合物在固相和液相（二甲基亚砜溶液）中均呈胺互变异构形式。在两种异构体中，[(三氟甲基)苯基]氨基残基相对于噻唑酮系统呈现同平面构象，而5-[(二甲基氨基)亚甲基]残基则采用Z构型。密度泛函理论（DFT）计算正确预测了两种异构体都倾向于共平面排列。在晶体中，对位化合物的整个独立分子在两个替代位置上无序，占据因子为 0.926 (3) 和 0.074 (3)。

更新日期：2023-10-24

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