Crystal Structure of 4-Methylbenzenecarbothioic Acid and Computational Investigations of Benzenecarbochalcogenoic Acids (C<sub>6</sub>H<sub>5</sub>COEH and C<sub>6</sub>H<sub>5</sub>CEOH, E = S, Se, Te)

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  • Kato Shinzi
    Department of Applied Chemistry, School of Engineering, Chubu University Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University
  • Niyomura Osamu
    Department of Applied Chemistry, School of Engineering, Chubu University Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University
  • Ebihara Masahiro
    Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University
  • Guo Jing-Dong
    Fukui Institute for Fundamental Chemistry, Kyoto University
  • Nagase Shigeru
    Fukui Institute for Fundamental Chemistry, Kyoto University

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  • Crystal Structure of 4-Methylbenzenecarbothioic Acid and Computational Investigations of Benzenecarbochalcogenoic Acids (C₆H₅COEH and C₆H₅CEOH, E = S, Se, Te)

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The X-ray structure analysis of arenecarbochalcogenoic acids (ArCOEH and ArCEOH, E = S, Se, Te) is successful for 4-MeC6H4COSH for the first time, which reveals that the syn-conformer forms a planar cyclic dimer with two S–H···O=C hydrogen bonds in the solid state. Density functional theory calculations are performed for benzenecarbochalcogenoic acids (C6H5COEH and C6H5CEOH), the tetrahydrofuran (THF)-solvated acids, and the cyclic dimers of the acids. It is suggested that arenechalcogenol acids (ArCOEH) form cyclic dimers in the solid state, although Della Védova and co-workers reported that catemeric hydrogen-bonding chains are observed for the crystal structures of selenoacetic acid (MeCOSeH). Calculations demonstrate that arenecarbochalcogenoic acids exist predominantly as chalcogenoxo tautomers (ArCEOH) in polar solvents such as THF especially at low temperatures, unlike the solid-state cases, which are consistent with several experimental results.

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