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Issue 19, 2003
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Crystal structures and properties of mutagenic N-acyloxy-N-alkoxyamides — “most pyramidal” acyclic amides

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Abstract

X-Ray data for two N-acyloxy-N-alkoxyamides, a class of direct-acting mutagens, indicate extreme pyramidalisation at the amide nitrogen in keeping with spectroscopic and theoretically determined properties of amides with bisoxo-substitution at nitrogen. The combined electronegativity of two oxygens leads to average angles at nitrogen of 107.8 and 108.1° and |χN| of 66° and 65°. The sp3 nature of nitrogen results in negligible amide resonance as evidenced by long N–C(O) bonds, high IR carbonyl stretch frequencies, carbonyl 13C NMR data and very low amide isomerisation barriers. In addition, conformations in the solid state support a strong nO–σ*NOAc anomeric interaction as predicted by molecular orbital theory. HF/6-31G* calculations on formamide, N-methoxyformamide and N-formyloxy-N-methoxyformamide support these findings.

Graphical abstract: Crystal structures and properties of mutagenic N-acyloxy-N-alkoxyamides — “most pyramidal” acyclic amides

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Article information


Submitted
29 May 2003
Accepted
31 Jul 2003
First published
27 Aug 2003

Org. Biomol. Chem., 2003,1, 3430-3437
Article type
Paper

Crystal structures and properties of mutagenic N-acyloxy-N-alkoxyamides — “most pyramidal” acyclic amides

A. E. Gillson, S. A. Glover, D. J. Tucker and P. Turner, Org. Biomol. Chem., 2003, 1, 3430
DOI: 10.1039/B306098P

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