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Title: Crystal structures and properties of mutagenic 'N'-acyloxy-'N'-alkoxyamides - 'most pyramidal' acyclic amides
Contributor(s): Gillson, Ashley-Mae (author); Glover, Stephen  (author)orcid ; Tucker, David  (author); Turner, P (author)
Publication Date: 2003
DOI: 10.1039/b306098p
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Abstract: X-Ray data for two N-acyloxy-N-alkoxyamides, a class of direct-acting mutagens, indicate extreme pyramidalisationat the amide nitrogen in keeping with spectroscopic and theoretically determined properties of amides with bisoxosubstitutionat nitrogen. The combined electronegativity of two oxygens leads to average angles at nitrogen of 107.8and 108.1° and |χN| of 66° and 65°. The sp³ nature of nitrogen results in negligible amide resonance as evidencedby long N–C(O) bonds, high IR carbonyl stretch frequencies, carbonyl ¹³C NMR data and very low amideisomerisation barriers. In addition, conformations in the solid state support a strong n₀–σ*[NOAc] anomeric interactionas predicted by molecular orbital theory. HF/6-31G* calculations on formamide, N-methoxyformamide andN-formyloxy-N-methoxyformamide support these findings.
Publication Type: Journal Article
Source of Publication: Organic & Biomolecular Chemistry, 1(0), p. 3430-3437
Publisher: Royal Society of Chemistry
Place of Publication: United Kingdom
ISSN: 1477-0539
Fields of Research (FoR) 2008: 030505 Physical Organic Chemistry
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article

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