Structural and IR-spectroscopic evidence of S–H···Ph hydrogen bonding in the solid state

Abstract

Structural and IR spetroscopic evidence is given for S–H···Ph hydrogen bonding in the solid state, an effect previously only known in solution. In the crystalline thiol N-(o-hydroxyphenyl)-3-sulfanylmethylpyrrolidin-2-one, hydrogen bond energies based on red shifts of the infrared S–H stretching marks are estimated as slightly below 0.5 (in benzene) and 1.0 (solid state) kcal mol^-1.