Please use this identifier to cite or link to this item: https://une.intersearch.com.au/unejspui/handle/1959.11/1347
Title: Crystal structures and properties of mutagenic 'N'-acyloxy-'N'-alkoxyamides - 'most pyramidal' acyclic amides
Contributor(s): Gillson, Ashley-Mae (author); Glover, Stephen  (author); Tucker, David  (author); Turner, P (author)
Publication Date: 2003
DOI: 10.1039/b306098p
Handle Link: https://hdl.handle.net/1959.11/1347
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: Cambridge, England
ISSN: 1477-0520
Field of Research (FOR): 030505 Physical Organic Chemistry
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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