Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides

Jonathan Clayden; Catherine McCarthy; Madeleine Helliwell

doi:10.1039/A906398F

Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides

Jonathan Clayden^*, Catherine McCarthy, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

54 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	2059-2060
Number of pages	2
Journal	Chemical Communications
Issue number	20
DOIs	https://doi.org/10.1039/A906398F
Publication status	Published - 21 Oct 1999

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title = "Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides",

abstract = "8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds at room temperature, and the rate at which they racemise (by rotation about the Ar-CO bond) depends principally on the extent to which the 8-substituent undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.",

author = "Jonathan Clayden and Catherine McCarthy and Madeleine Helliwell",

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AU - Clayden, Jonathan

AU - McCarthy, Catherine

AU - Helliwell, Madeleine

PY - 1999/10/21

Y1 - 1999/10/21

N2 - 8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds at room temperature, and the rate at which they racemise (by rotation about the Ar-CO bond) depends principally on the extent to which the 8-substituent undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.

AB - 8-Substituted tertiary 1-naphthamides are chiral, atropisomeric compounds at room temperature, and the rate at which they racemise (by rotation about the Ar-CO bond) depends principally on the extent to which the 8-substituent undergoes incipient nucleophilic addition to the amide carbonyl group, as indicated by X-ray crystallography.

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U2 - 10.1039/A906398F

DO - 10.1039/A906398F

M3 - Article (Academic Journal)

AN - SCOPUS:0033592658

SP - 2059

EP - 2060

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 20

ER -

Bonded peri-interactions govern the rate of racemisation of atropisomeric 8-substituted 1-naphthamides

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