Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols

James H. Clark; David G. Cork; Julie A. Tinsdale

doi:10.1016/0584-8539(86)80110-6

Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols

James H. Clark^*, David G. Cork, Julie A. Tinsdale

^*Corresponding author for this work

Chemistry

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

Abstract

Infrared spectra of tetrabutylammonium fluoride complexes of both 4-cyanophenol and methyl-4-hydroxybenzoate but not 3-cyanophenol reveal the presence of two distinct types of hydrogen bond corresponding to charge localized and partially charge delocalized forms. The latter only occur in polar aprotic protophilic solvents at low temperatures. The activation energies for the interconversion of the two forms reflect the relative abilities of the two groups to delocalize charge through resonance. The chemical shifts of the aromatic protons of the complexes are also medium dependent although the precise nature of this medium dependence is less easily understood.

Original language	English
Pages (from-to)	815-819
Number of pages	5
Journal	Spectrochimica Acta Part A: Molecular Spectroscopy
Volume	42
Issue number	7
DOIs	https://doi.org/10.1016/0584-8539(86)80110-6
Publication status	Published - 1 Jan 1986

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10.1016/0584-8539(86)80110-6

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title = "Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols",

abstract = "Infrared spectra of tetrabutylammonium fluoride complexes of both 4-cyanophenol and methyl-4-hydroxybenzoate but not 3-cyanophenol reveal the presence of two distinct types of hydrogen bond corresponding to charge localized and partially charge delocalized forms. The latter only occur in polar aprotic protophilic solvents at low temperatures. The activation energies for the interconversion of the two forms reflect the relative abilities of the two groups to delocalize charge through resonance. The chemical shifts of the aromatic protons of the complexes are also medium dependent although the precise nature of this medium dependence is less easily understood.",

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Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols. / Clark, James H.; Cork, David G.; Tinsdale, Julie A.
In: Spectrochimica Acta Part A: Molecular Spectroscopy, Vol. 42, No. 7, 01.01.1986, p. 815-819.

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

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T1 - Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols

AU - Clark, James H.

AU - Cork, David G.

AU - Tinsdale, Julie A.

PY - 1986/1/1

Y1 - 1986/1/1

N2 - Infrared spectra of tetrabutylammonium fluoride complexes of both 4-cyanophenol and methyl-4-hydroxybenzoate but not 3-cyanophenol reveal the presence of two distinct types of hydrogen bond corresponding to charge localized and partially charge delocalized forms. The latter only occur in polar aprotic protophilic solvents at low temperatures. The activation energies for the interconversion of the two forms reflect the relative abilities of the two groups to delocalize charge through resonance. The chemical shifts of the aromatic protons of the complexes are also medium dependent although the precise nature of this medium dependence is less easily understood.

AB - Infrared spectra of tetrabutylammonium fluoride complexes of both 4-cyanophenol and methyl-4-hydroxybenzoate but not 3-cyanophenol reveal the presence of two distinct types of hydrogen bond corresponding to charge localized and partially charge delocalized forms. The latter only occur in polar aprotic protophilic solvents at low temperatures. The activation energies for the interconversion of the two forms reflect the relative abilities of the two groups to delocalize charge through resonance. The chemical shifts of the aromatic protons of the complexes are also medium dependent although the precise nature of this medium dependence is less easily understood.

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JF - Spectrochimica Acta Part A: Molecular Spectroscopy

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Spectroscopic evidence for medium controlled hydrogen bond inhibition of resonance delocalization of charge in complexes of tetrabutylammonium fluoride with phenols

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