Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR

Ryan A. Bragg; Jonathan Clayden

doi:10.1021/ol0064462

Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR

Ryan A. Bragg, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

27 Citations (Scopus)

Abstract

(matrix presented) Dynamic NMR proves that the fastest interconversion between conformers of simple tertiary aromatic amide 3 is racemization via a geared (correlated) rotation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that correlated and noncorrelated rotations are easily distinguishable, even without assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.

Original language	English
Pages (from-to)	3351-3354
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	21
Early online date	14 Sep 2000
DOIs	https://doi.org/10.1021/ol0064462
Publication status	Published - 19 Oct 2000

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title = "Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR",

abstract = "(matrix presented) Dynamic NMR proves that the fastest interconversion between conformers of simple tertiary aromatic amide 3 is racemization via a geared (correlated) rotation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that correlated and noncorrelated rotations are easily distinguishable, even without assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.",

author = "Bragg, {Ryan A.} and Jonathan Clayden",

year = "2000",

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doi = "10.1021/ol0064462",

language = "English",

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T1 - Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR

AU - Bragg, Ryan A.

AU - Clayden, Jonathan

PY - 2000/10/19

Y1 - 2000/10/19

N2 - (matrix presented) Dynamic NMR proves that the fastest interconversion between conformers of simple tertiary aromatic amide 3 is racemization via a geared (correlated) rotation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that correlated and noncorrelated rotations are easily distinguishable, even without assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.

AB - (matrix presented) Dynamic NMR proves that the fastest interconversion between conformers of simple tertiary aromatic amide 3 is racemization via a geared (correlated) rotation of both the Ar-CO and N-CO bonds. The symmetry of 3 is such that correlated and noncorrelated rotations are easily distinguishable, even without assignment of the NMR spectrum, simply by observing the number of peaks taking part in the exchange.

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U2 - 10.1021/ol0064462

DO - 10.1021/ol0064462

M3 - Article (Academic Journal)

AN - SCOPUS:0000870887

VL - 2

SP - 3351

EP - 3354

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -

Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR

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