Stereochemistry of dimesityl-9-anthrylmethane and bis(2,6-xylyl)-1-(2-methylnaphthyl)methane. Evidence for the two-ring flip mechanism in triarylmethanes

Paolo Finocchiaro, John Devens Gust, Kurt Mislow

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34 Citations (Scopus)

Abstract

The temperature-dependent 1H-nmr spectra of the title compounds indicate that these molecules adopt a propeller conformation in the ground state, and that a variety of interconversions of stereoisomeric molecules on the nmr time scale occurs at elevated temperatures. These interconversions are all shown to proceed by the tworing flip mechanism. The associated free energies of activation are reported. Comparison of the present results with the results of earlier studies on triarylmethanes, triarylboranes, and cognates brings to light that the two-ring flip mechanism is the favored stereoisomerization pathway for all of these systems.

Original languageEnglish
Pages (from-to)2176-2182
Number of pages7
JournalJournal of the American Chemical Society
Volume96
Issue number7
Publication statusPublished - 1974

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Stereochemistry
Methane
Molecules
Temperature
Propellers
Ground state
Free energy
Conformations
Chemical activation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "The temperature-dependent 1H-nmr spectra of the title compounds indicate that these molecules adopt a propeller conformation in the ground state, and that a variety of interconversions of stereoisomeric molecules on the nmr time scale occurs at elevated temperatures. These interconversions are all shown to proceed by the tworing flip mechanism. The associated free energies of activation are reported. Comparison of the present results with the results of earlier studies on triarylmethanes, triarylboranes, and cognates brings to light that the two-ring flip mechanism is the favored stereoisomerization pathway for all of these systems.",
author = "Paolo Finocchiaro and Gust, {John Devens} and Kurt Mislow",
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T1 - Stereochemistry of dimesityl-9-anthrylmethane and bis(2,6-xylyl)-1-(2-methylnaphthyl)methane. Evidence for the two-ring flip mechanism in triarylmethanes

AU - Finocchiaro, Paolo

AU - Gust, John Devens

AU - Mislow, Kurt

PY - 1974

Y1 - 1974

N2 - The temperature-dependent 1H-nmr spectra of the title compounds indicate that these molecules adopt a propeller conformation in the ground state, and that a variety of interconversions of stereoisomeric molecules on the nmr time scale occurs at elevated temperatures. These interconversions are all shown to proceed by the tworing flip mechanism. The associated free energies of activation are reported. Comparison of the present results with the results of earlier studies on triarylmethanes, triarylboranes, and cognates brings to light that the two-ring flip mechanism is the favored stereoisomerization pathway for all of these systems.

AB - The temperature-dependent 1H-nmr spectra of the title compounds indicate that these molecules adopt a propeller conformation in the ground state, and that a variety of interconversions of stereoisomeric molecules on the nmr time scale occurs at elevated temperatures. These interconversions are all shown to proceed by the tworing flip mechanism. The associated free energies of activation are reported. Comparison of the present results with the results of earlier studies on triarylmethanes, triarylboranes, and cognates brings to light that the two-ring flip mechanism is the favored stereoisomerization pathway for all of these systems.

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