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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Crystal Structures of the Amide and Iminol Tautomers O-(3,5-dinitrobenzoyloxy)benzohydroxamate. A Case of a Disappearing Solvate?

Abigail L. Albright A , Lucy Collins A , John Li A , Benjamin Harris A and Jonathan M. White A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Bio21 Institute, The University of Melbourne, Parkville 3010, Australia.

B Corresponding author. Email: whitejm@unimelb.edu.au

Australian Journal of Chemistry 69(10) 1193-1197 https://doi.org/10.1071/CH16369
Submitted: 21 June 2016  Accepted: 15 July 2016   Published: 5 August 2016

Abstract

The O-(3,5-dinitrobenzoyl) derivative of benzohydroxamic acid 1 crystallizes in its iminol tautomeric form, hydrogen bonded to a molecule of dimethyl sulfoxide (DMSO) when crystallized from methanol in the presence of DMSO. In contrast, in the absence of DMSO, 1 crystallizes in its amide tautomeric form. Computations suggest that in the absence of DMSO, the amide tautomer of 1 is significantly more stable than the iminol form. Conversely, in the presence of DMSO, the two forms have comparable stabilities. Solution infrared spectra of 1 run in dichloromethane are consistent with the amide tautomeric form predominating; however, titration of aliquots of DMSO results in the formation of a second species with spectral characteristics consistent with the iminol tautomer.


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