Side-chain rotational processes in pentaethylated benzenes

Hugo E. Gottlieb; Caroline Ben-Ari; Alfred Hassner; Vered Marks

doi:10.1016/s0040-4020(99)00088-5

Side-chain rotational processes in pentaethylated benzenes

Hugo E. Gottlieb
, Caroline Ben-Ari
, Alfred Hassner
, Vered Marks

Department of Chemistry

Weizmann Institute of Science
Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The barriers for conformational exchange processes in pentaethylbenzenes C₆Et₅R (R = H, Br, COCH₃, OCOCH₃ and OCOPh) were determined by NMR lineshape analysis; for the latter three substances these processes include both the stepwise rotation of the ethyl groups and the 180°reorientation of the side-chain R. The experimental barriers were compared to those calculated by molecular mechanics (MM3). These results have implications in the long- standing argument about the barrier of ethyl group rotation in hexaethylbenzene (R = Et) and some of its metal complexes.

Original language	English
Pages (from-to)	4003-4014
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	13
DOIs	https://doi.org/10.1016/s0040-4020(99)00088-5
State	Published - 26 Mar 1999

Keywords

Benzenes
Conformation
Molecular mechanics
NMR

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10.1016/s0040-4020(99)00088-5

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title = "Side-chain rotational processes in pentaethylated benzenes",

abstract = "The barriers for conformational exchange processes in pentaethylbenzenes C6Et5R (R = H, Br, COCH3, OCOCH3 and OCOPh) were determined by NMR lineshape analysis; for the latter three substances these processes include both the stepwise rotation of the ethyl groups and the 180°reorientation of the side-chain R. The experimental barriers were compared to those calculated by molecular mechanics (MM3). These results have implications in the long- standing argument about the barrier of ethyl group rotation in hexaethylbenzene (R = Et) and some of its metal complexes.",

keywords = "Benzenes, Conformation, Molecular mechanics, NMR",

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T1 - Side-chain rotational processes in pentaethylated benzenes

AU - Gottlieb, Hugo E.

AU - Ben-Ari, Caroline

AU - Hassner, Alfred

AU - Marks, Vered

PY - 1999/3/26

Y1 - 1999/3/26

N2 - The barriers for conformational exchange processes in pentaethylbenzenes C6Et5R (R = H, Br, COCH3, OCOCH3 and OCOPh) were determined by NMR lineshape analysis; for the latter three substances these processes include both the stepwise rotation of the ethyl groups and the 180°reorientation of the side-chain R. The experimental barriers were compared to those calculated by molecular mechanics (MM3). These results have implications in the long- standing argument about the barrier of ethyl group rotation in hexaethylbenzene (R = Et) and some of its metal complexes.

AB - The barriers for conformational exchange processes in pentaethylbenzenes C6Et5R (R = H, Br, COCH3, OCOCH3 and OCOPh) were determined by NMR lineshape analysis; for the latter three substances these processes include both the stepwise rotation of the ethyl groups and the 180°reorientation of the side-chain R. The experimental barriers were compared to those calculated by molecular mechanics (MM3). These results have implications in the long- standing argument about the barrier of ethyl group rotation in hexaethylbenzene (R = Et) and some of its metal complexes.

KW - Benzenes

KW - Conformation

KW - Molecular mechanics

KW - NMR

UR - https://www.scopus.com/pages/publications/0033605829

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EP - 4014

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

Side-chain rotational processes in pentaethylated benzenes

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Keywords

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