Synthesis, crystal structure and Hirshfeld surface analysis of tert-butyl N-acetylcarbamate

Abstract

This article reports a practical synthesis of tert-butyl acetylcarbamate, C7H13NO3, from N-Boc-thioacetamide and the study of its crystal structure. The reaction proceeds in the presence of natural phosphate as a catalyst, with excellent yield, simple workup and benign environment. The crystal structure was refined using a transferred multipolar atom model. In the crystal, symmetrical pairs of strong N—H...O hydrogen bonds connect the molecules into dimers with an R22(8) ring motif. The interactions between neighbouring dimers are mostly van der Waals, between hydrophobic methyl groups. Hirshfeld surface analysis shows the major contributions to the crystal packing are from H...H (42.6%) and O...H (26.7%) contacts.

Keywords

• x-ray crystal structure
• tert-butyl acetylcarbamate
• natural phosphate
• mauritanian phosphate deposit