N-(4-Bromophenyl)methoxycarbothioamide

• Main Authors: Chien Ing Yeo, Edward R.T. Tiekink
• Format: Article
• Language: English
• Published: MDPI AG 2018-08-01
• Series: Molbank
• Subjects: carbothioamide; thiocarbamate; X-ray crystallography; hydrogen bonding
• Online Access: http://www.mdpi.com/1422-8599/2018/3/M1012

The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C‒S and C‒N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N‒H atoms are syn, enabling the formation of amide-N‒H…S(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered {…HNCS}2 synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Br…π(4-bromophenyl), S…π(4-bromophenyl), and weak Br…S halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N‒H…S(thione) hydrogen bonding in the crystal conform with expectation for this class of compound.