Protonation-induced conformational changes of 2-(N,N-dimethylamino)ethanethiol. Importance of strong N-H+ center dot center dot center dot S and N-H+ center dot center dot center dot S-hydrogen bonding

Ohno K; Matsumoto S; Aida M; Matsuura H

Chemistry Letters, Vol.32, No.9, 828-829, 2003

DOI10.1246/cl.2003.828 Export Citation

Protonation-induced conformational changes of 2-(N,N-dimethylamino)ethanethiol. Importance of strong N-H+ center dot center dot center dot S and N-H+ center dot center dot center dot S-hydrogen bonding

Ohno K, Matsumoto S, Aida M, Matsuura H

2-(N,N-Dimethylamino)ethanethiol exists in aqueous solution as a cation, zwitterion, or anion in different pH regions. Me2NH+EtSH and Me2NH+EtS- assume the gauche conformation around the NC-CS bond, as stabilized by strong intramolecular 1,4-N-H+...S and 1,4-N-H+...S-hydrogen bondings, respectively, while Me2NEtS- assumes the trans conformation around the same bond.