Barriers to rotation about the chiral axis of tertiary aromatic amides

Anjum Ahmed*, Ryan A. Bragg, Jonathan Clayden, Lai Wah Lai, Catherine McCarthy, Jennifer H. Pink, Neil Westlund, Samreen A. Yasin

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

173 Citations (Scopus)

Abstract

The barrier to rotation about the aryl-carbonyl bond in 40 tertiary aromatic amides was determined by variable temperature NMR spectroscopy (for rapid rotations) or by following the interconversion of atropisomers (for slower rotations). Empirical guidelines to the rate of Ar-CO bond rotation in hindered tertiary aromatic amides, and hence the stability of the atropisomeric stereoisomers of axially chiral amides, are presented.

Original languageEnglish
Pages (from-to)13277-13294
Number of pages18
JournalTetrahedron
Volume54
Issue number43
DOIs
Publication statusPublished - 22 Oct 1998

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