Proton tautomerism and stereoisomerism in isomeric 4-(metoxyphenyl)amino-1,3-thiazol-2(5H)-one derivatives: Synthesis, crystal structure and spectroscopic studies

Pyrih, Andrii; Łapiński, Andrzej; Zięba, Sylwia; Mizera, Adam; Lesyk, Roman; Gzella, Andrzej K.; Jaskolski, Mariusz

doi:10.1016/j.molstruc.2023.136748

Journal of Molecular Structure

2024

DOI: 10.1016/j.molstruc.2023.136748

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Proton tautomerism and stereoisomerism in isomeric 4-(metoxyphenyl)amino-1,3-thiazol-2(5H)-one derivatives: Synthesis, crystal structure and spectroscopic studies

Andrii Pyrih,

Andrzej Łapiński,

Sylwia Zięba

et al.

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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

Pyrih,

Łapiński,

Zięba

et al. 2023

Acta Crystallogr C

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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).

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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

Pyrih,

Łapiński,

Zięba

et al. 2023

Acta Crystallogr C

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Proton tautomerism and stereoisomerism in isomeric 4-(metoxyphenyl)amino-1,3-thiazol-2(5H)-one derivatives: Synthesis, crystal structure and spectroscopic studies

Cited by 1 publication

References 38 publications

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

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

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