Conformational dynamics of polyarylbenzenes. Buttressing effects

Alan Patton, Jennie Wang Dirks, John Devens Gust

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The free energies of activation for rotational stereoisomerization of a series of pentaarylbenzenes have been measured. The results reveal that substantial steric effects are transmitted around the circumference of the central aryl ring from sites remote from the rotating rings. The free energies of activation for compounds bearing various substituents on the central ring range from 15.5 to 18.7 kcal/mol and obey a linear relationship with respect to -ΔG° for the same substituents in the axial-equatorial cyclohexane equilibrium. This relationship permits the estimation of -ΔG° for additional substituents. The value for the 1-hydroxyethyl group was found to be 1.8 kcal/mol, whereas a lower limit of 5.6 kcal/mol was determined for the tert-butyl group.

Original languageEnglish
Pages (from-to)4749-4752
Number of pages4
JournalJournal of Organic Chemistry
Volume44
Issue number26
Publication statusPublished - 1979

Fingerprint

Free energy
Bearings (structural)
Chemical activation
Cyclohexane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Conformational dynamics of polyarylbenzenes. Buttressing effects. / Patton, Alan; Dirks, Jennie Wang; Gust, John Devens.

In: Journal of Organic Chemistry, Vol. 44, No. 26, 1979, p. 4749-4752.

Research output: Contribution to journalArticle

Patton, Alan ; Dirks, Jennie Wang ; Gust, John Devens. / Conformational dynamics of polyarylbenzenes. Buttressing effects. In: Journal of Organic Chemistry. 1979 ; Vol. 44, No. 26. pp. 4749-4752.
@article{20e8eb03caff427eb8f164b1729d7d63,
title = "Conformational dynamics of polyarylbenzenes. Buttressing effects",
abstract = "The free energies of activation for rotational stereoisomerization of a series of pentaarylbenzenes have been measured. The results reveal that substantial steric effects are transmitted around the circumference of the central aryl ring from sites remote from the rotating rings. The free energies of activation for compounds bearing various substituents on the central ring range from 15.5 to 18.7 kcal/mol and obey a linear relationship with respect to -ΔG° for the same substituents in the axial-equatorial cyclohexane equilibrium. This relationship permits the estimation of -ΔG° for additional substituents. The value for the 1-hydroxyethyl group was found to be 1.8 kcal/mol, whereas a lower limit of 5.6 kcal/mol was determined for the tert-butyl group.",
author = "Alan Patton and Dirks, {Jennie Wang} and Gust, {John Devens}",
year = "1979",
language = "English",
volume = "44",
pages = "4749--4752",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "26",

}

TY - JOUR

T1 - Conformational dynamics of polyarylbenzenes. Buttressing effects

AU - Patton, Alan

AU - Dirks, Jennie Wang

AU - Gust, John Devens

PY - 1979

Y1 - 1979

N2 - The free energies of activation for rotational stereoisomerization of a series of pentaarylbenzenes have been measured. The results reveal that substantial steric effects are transmitted around the circumference of the central aryl ring from sites remote from the rotating rings. The free energies of activation for compounds bearing various substituents on the central ring range from 15.5 to 18.7 kcal/mol and obey a linear relationship with respect to -ΔG° for the same substituents in the axial-equatorial cyclohexane equilibrium. This relationship permits the estimation of -ΔG° for additional substituents. The value for the 1-hydroxyethyl group was found to be 1.8 kcal/mol, whereas a lower limit of 5.6 kcal/mol was determined for the tert-butyl group.

AB - The free energies of activation for rotational stereoisomerization of a series of pentaarylbenzenes have been measured. The results reveal that substantial steric effects are transmitted around the circumference of the central aryl ring from sites remote from the rotating rings. The free energies of activation for compounds bearing various substituents on the central ring range from 15.5 to 18.7 kcal/mol and obey a linear relationship with respect to -ΔG° for the same substituents in the axial-equatorial cyclohexane equilibrium. This relationship permits the estimation of -ΔG° for additional substituents. The value for the 1-hydroxyethyl group was found to be 1.8 kcal/mol, whereas a lower limit of 5.6 kcal/mol was determined for the tert-butyl group.

UR - http://www.scopus.com/inward/record.url?scp=0000345920&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000345920&partnerID=8YFLogxK

M3 - Article

VL - 44

SP - 4749

EP - 4752

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 26

ER -