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

doi:10.1016/S0040-4020(98)00814-X

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

School of Chemistry

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

197 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 language	English
Pages (from-to)	13277-13294
Number of pages	18
Journal	Tetrahedron
Volume	54
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4020(98)00814-X
Publication status	Published - 22 Oct 1998

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Organic & Biological

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title = "Barriers to rotation about the chiral axis of tertiary aromatic amides",

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.",

author = "Anjum Ahmed and Bragg, \{Ryan A.\} and Jonathan Clayden and Lai, \{Lai Wah\} and Catherine McCarthy and Pink, \{Jennifer H.\} and Neil Westlund and Yasin, \{Samreen A.\}",

year = "1998",

month = oct,

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doi = "10.1016/S0040-4020(98)00814-X",

language = "English",

volume = "54",

pages = "13277--13294",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Barriers to rotation about the chiral axis of tertiary aromatic amides

AU - Ahmed, Anjum

AU - Bragg, Ryan A.

AU - Clayden, Jonathan

AU - Lai, Lai Wah

AU - McCarthy, Catherine

AU - Pink, Jennifer H.

AU - Westlund, Neil

AU - Yasin, Samreen A.

PY - 1998/10/22

Y1 - 1998/10/22

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0032558599

U2 - 10.1016/S0040-4020(98)00814-X

DO - 10.1016/S0040-4020(98)00814-X

M3 - Article (Academic Journal)

AN - SCOPUS:0032558599

SN - 0040-4020

VL - 54

SP - 13277

EP - 13294

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

Barriers to rotation about the chiral axis of tertiary aromatic amides

Abstract

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