Conversion of thiol to homodisulfide-Schiff base derivative: Synthesis, molecular structure, crystal structure and DFT studies

Abstract

Facile conversion of a thiol-Schiff base (obtained from the condensation of 2-hydroxynaphthaldehyde and 2-aminothiophenol) to the corresponding homodisulfide derivative is described. The molecular structure and stoichiometry of the thiol (1) and disulfide (2) compounds were characterized by analytical and spectroscopic techniques. The structure of the disulfide derivative was also confirmed by single crystal X-ray analysis. Theoretical calculations based on density functional theory (DFT) were established to verify the structures of the thiol in both solid and solution forms as well the structure of the disulfide. The global chemical reactivity descriptors were estimated from the energy of the HOMO and LUMO orbitals.