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Intramolecular Hydrogen Bonds. XVII. Intramolecular Hydrogen Bonding Involving the Mercapto Group as a Hydrogen Donor

1971; Oxford University Press; Volume: 44; Issue: 7 Linguagem: Inglês

10.1246/bcsj.44.1858

1348-0634

Nobuo Mōri, Shinichi Kaido, Koichi Suzuki, Mikio Nakamura, Yojiro Tsuzuki,

Analytical Chemistry and Chromatography

Abstract The SH stretching absorption spectra of some mercapto compounds in dilute carbon tetrachloride solutions and also in acetonitrile solutions have been measured at 20°C. Alkyl mercaptans show absorption bands which are suggestive of the rotational isomerism around the C–S bond. The spectral data indicate that benzyl mercaptan, ω-ethoxyalkyl mercaptans, and ethyl α- and β-mercaptoalkanoates form practically no intramolecular hydrogen bond between the SH group and the hydrogen-acceptor group. In thiosalicylic acid and its ethyl ester, the hydrogen-bonding to the carbonyl group is partially possible even in acetonitrile. On the other hand, the corresponding free carboxylic acids are not hydrogen-bonded between the S atom and the carboxyl group.