Volume 31, Issue 5
Isocyclic Compounds
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ChemInform Abstract: Bonded peri-Interactions Govern the Rate of Racemization of Atropisomeric 8-Substituted 1-Naphthamides.

Jonathan Clayden

Jonathan Clayden

Dep. Chem., Victoria Univ., Manchester M13 9PL, UK

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Catherine McCarthy

Catherine McCarthy

Dep. Chem., Victoria Univ., Manchester M13 9PL, UK

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Madeleine Helliwell

Madeleine Helliwell

Dep. Chem., Victoria Univ., Manchester M13 9PL, UK

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First published: 11 June 2010

Abstract

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ChemInform Abstract

8-Substituted tertiary 1-naphthamides (I), (II) are chiral, atropisomeric compounds at room temperature, and the rate at which they racemize depends on the extent to which the 8-substituent undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.

chemical structure image

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