Competitive N–H⋯OC and N–H⋯SC hydrogen bonding in alanine dithiocarbamates

Abstract

The crystal structures of a homologous family of alanine-based dithiocarbamates reveal structural patterns influenced by intermolecular O–H⋯O, N–H⋯O and N–H⋯S interactions. These chemical systems differ by the steric properties of the pendent alkyl groups (i.e., methyl, ethyl, isopropyl and benzyl). Although a carboxylic acid head-to-head dimer provides a common theme for these structures, variations in molecular alignment arise from the use of the dithiocarbamate N–H donor group in either N–H⋯OC or N–H⋯SC interactions. The molecular features and crystal structure patterns responsible for the competitive self-assembly provide the basis of discussion.