The effect of substituents on the deprotonation energy of selected primary, secondary and tertiary alcohols

J. Mestres; M. Duran; J. Bertrán; I. G. Csizmadia

doi:10.1016/0166-1280(95)04353-5

The effect of substituents on the deprotonation energy of selected primary, secondary and tertiary alcohols

J. Mestres, M. Duran, J. Bertrán, I. G. Csizmadia

Department of Chemistry

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

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Abstract

Ab initio computations were carried out at the Hartree-Fock level of theory on primary, secondary and tertiary alcohols and also on their deprotonated conjugate bases containing methyl and phenyl substituents using a variety of basis sets (3-21G, 6-31G and triple-zeta) in combination with diffuse and polarization functions. The computed gas phase acidity as measured by the proton affinity of the conjugate bases (alkoxide ions) increased with increasing degree of substitution, in agreement with experimental gas phase acidity but in disagreement with experimental solution acidity trends. The molecular conformations, fundamental vibrational frequencies and charge distributions of selected alcohols and their conjugate bases were also studied. © 1995.

Original language	English
Pages (from-to)	229-249
Journal	Journal of Molecular Structure: THEOCHEM
Volume	358
Issue number	1-3 C
DOIs	https://doi.org/10.1016/0166-1280(95)04353-5
Publication status	Published - 14 Dec 1995

Keywords

Ab initio HF computation
Aliphatic and aromatic alcohols and their alkoxide ions
Gas phase acidity
Vibrational spectral data

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title = "The effect of substituents on the deprotonation energy of selected primary, secondary and tertiary alcohols",

abstract = "Ab initio computations were carried out at the Hartree-Fock level of theory on primary, secondary and tertiary alcohols and also on their deprotonated conjugate bases containing methyl and phenyl substituents using a variety of basis sets (3-21G, 6-31G and triple-zeta) in combination with diffuse and polarization functions. The computed gas phase acidity as measured by the proton affinity of the conjugate bases (alkoxide ions) increased with increasing degree of substitution, in agreement with experimental gas phase acidity but in disagreement with experimental solution acidity trends. The molecular conformations, fundamental vibrational frequencies and charge distributions of selected alcohols and their conjugate bases were also studied. {\textcopyright} 1995.",

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T1 - The effect of substituents on the deprotonation energy of selected primary, secondary and tertiary alcohols

AU - Mestres, J.

AU - Duran, M.

AU - Bertrán, J.

AU - Csizmadia, I. G.

PY - 1995/12/14

Y1 - 1995/12/14

N2 - Ab initio computations were carried out at the Hartree-Fock level of theory on primary, secondary and tertiary alcohols and also on their deprotonated conjugate bases containing methyl and phenyl substituents using a variety of basis sets (3-21G, 6-31G and triple-zeta) in combination with diffuse and polarization functions. The computed gas phase acidity as measured by the proton affinity of the conjugate bases (alkoxide ions) increased with increasing degree of substitution, in agreement with experimental gas phase acidity but in disagreement with experimental solution acidity trends. The molecular conformations, fundamental vibrational frequencies and charge distributions of selected alcohols and their conjugate bases were also studied. © 1995.

AB - Ab initio computations were carried out at the Hartree-Fock level of theory on primary, secondary and tertiary alcohols and also on their deprotonated conjugate bases containing methyl and phenyl substituents using a variety of basis sets (3-21G, 6-31G and triple-zeta) in combination with diffuse and polarization functions. The computed gas phase acidity as measured by the proton affinity of the conjugate bases (alkoxide ions) increased with increasing degree of substitution, in agreement with experimental gas phase acidity but in disagreement with experimental solution acidity trends. The molecular conformations, fundamental vibrational frequencies and charge distributions of selected alcohols and their conjugate bases were also studied. © 1995.

KW - Ab initio HF computation

KW - Aliphatic and aromatic alcohols and their alkoxide ions

KW - Gas phase acidity

KW - Vibrational spectral data

U2 - 10.1016/0166-1280(95)04353-5

DO - 10.1016/0166-1280(95)04353-5

M3 - Article

VL - 358

SP - 229

EP - 249

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

IS - 1-3 C

ER -