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Understanding the Solid-State Assembly of Pharmaceutically-Relevant N,N-Dimethyl-O-Thiocarbamates in the Absence of Labile Hydrogen Bonds

preprint
submitted on 13.09.2020, 09:08 and posted on 14.09.2020, 10:53 by Davin Tan, Zi xuan Ng, Rakesh Ganguly, yongxin Li, Han Sen Soo, Felipe Garcia
There are many pharmaceutical compounds that do not contain N-H, O-H, and S-H hydrogen-bond donor functional groups. Some of these compounds are N,N-disubstituted O-thiocarbamates which exhibit desirable medicinal properties, yet the study of these important molecules in the solid-state has been relatively unexplored. Herein, we report the synthesis and analysis of a series of N,N-dimethyl-O-thiocarbamates, and use X-ray diffraction techniques to gain insight into how these molecules self-assemble in the solid-state and discern certain packing patterns. It was observed that the aryl-thiocarbamate C-O bonds are twisted such that the planar aryl and carbamate moieties are orthogonal. Such a non-planar molecular geometry affects the way the molecules pack and crystal structure analyses revealed four general modes in which the molecules can associate in the solid-state, with some members of the series displaying isostructural relationships. The crystal structure of a well-known yet unreported O-thiocarbamate drug, Tolnaftate, is also reported. Additionally, Hirshfeld surface analysis was also performed on these compounds as well as several related O-thiocarbamates in the literature.

Funding

A*STAR AME IRG (A1783c0003)

NTU start-up grant (M4080552)

MOE Tier 1 grant RG 111/18

MOE Tier 1 grant RT 05/19.

AME IRG grant A1783c0003

AME IRG grant A1783c0002

AME IRG grant A1783c0007

History

Email Address of Submitting Author

fgarcia@ntu.edu.sg

Institution

Nanyang Technological University

Country

Signapore

ORCID For Submitting Author

0000-0002-9605-3611

Declaration of Conflict of Interest

The authors declare no conflict of interest

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