Role of secondary interactions in the conformational equilibrium of 2,6-diisopropylphenol

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Abstract

The experimental infrared spectrum of 2,6-diisopropylphenol in dilute CCl4 solution displaying absorptions at 3619 (intense) and 3641 cm-1 (shoulder) in the O-H stretching region cannot be satisfactorily reproduced by two symmetric band components. Ab initio quantum chemical calculations have identified five stable conformers differing in the relative orientations of the two ortho substituents, whereas DFT calculations yielded four different νOH frequencies for these conformers in agreement with the deconvolution and least-squares curve analysis of the experimental spectrum. The observed spectrum could be successfully simulated by the calculated frequencies and band intensities assigned to the five conformers on the basis of their relative stabilities.

Original languageEnglish
Pages (from-to)3471-3474
Number of pages4
JournalJournal of Physical Chemistry A
Volume105
Issue number14
Publication statusPublished - Apr 12 2001

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Propofol
Deconvolution
shoulders
Discrete Fourier transforms
Stretching
infrared spectra
interactions
Infrared radiation
curves

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

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title = "Role of secondary interactions in the conformational equilibrium of 2,6-diisopropylphenol",
abstract = "The experimental infrared spectrum of 2,6-diisopropylphenol in dilute CCl4 solution displaying absorptions at 3619 (intense) and 3641 cm-1 (shoulder) in the O-H stretching region cannot be satisfactorily reproduced by two symmetric band components. Ab initio quantum chemical calculations have identified five stable conformers differing in the relative orientations of the two ortho substituents, whereas DFT calculations yielded four different νOH frequencies for these conformers in agreement with the deconvolution and least-squares curve analysis of the experimental spectrum. The observed spectrum could be successfully simulated by the calculated frequencies and band intensities assigned to the five conformers on the basis of their relative stabilities.",
author = "Zsolt Bik{\'a}di and G. Keresztury and S. Holly and O. Egyed and I. Mayer and M. Simonyi",
year = "2001",
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T1 - Role of secondary interactions in the conformational equilibrium of 2,6-diisopropylphenol

AU - Bikádi, Zsolt

AU - Keresztury, G.

AU - Holly, S.

AU - Egyed, O.

AU - Mayer, I.

AU - Simonyi, M.

PY - 2001/4/12

Y1 - 2001/4/12

N2 - The experimental infrared spectrum of 2,6-diisopropylphenol in dilute CCl4 solution displaying absorptions at 3619 (intense) and 3641 cm-1 (shoulder) in the O-H stretching region cannot be satisfactorily reproduced by two symmetric band components. Ab initio quantum chemical calculations have identified five stable conformers differing in the relative orientations of the two ortho substituents, whereas DFT calculations yielded four different νOH frequencies for these conformers in agreement with the deconvolution and least-squares curve analysis of the experimental spectrum. The observed spectrum could be successfully simulated by the calculated frequencies and band intensities assigned to the five conformers on the basis of their relative stabilities.

AB - The experimental infrared spectrum of 2,6-diisopropylphenol in dilute CCl4 solution displaying absorptions at 3619 (intense) and 3641 cm-1 (shoulder) in the O-H stretching region cannot be satisfactorily reproduced by two symmetric band components. Ab initio quantum chemical calculations have identified five stable conformers differing in the relative orientations of the two ortho substituents, whereas DFT calculations yielded four different νOH frequencies for these conformers in agreement with the deconvolution and least-squares curve analysis of the experimental spectrum. The observed spectrum could be successfully simulated by the calculated frequencies and band intensities assigned to the five conformers on the basis of their relative stabilities.

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