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Int. J. Mol. Sci. 2002, 3(4), 407-422; doi:10.3390/i3040407

The O-H Bond Dissociation Energies of Substituted Phenols and Proton Affinities of Substituted Phenoxide Ions: A DFT Study

1
Research Institute of Innovative Technology for the Earth (RITE), National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central 5, Tsukuba 305-8565, Japan
2
National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central 5, Tsukuba 305-8565, Japan
*
Author to whom correspondence should be addressed.
Received: 25 September 2001 / Accepted: 7 January 2002 / Published: 25 April 2002
(This article belongs to the Special Issue Application of Density Functional Theory)
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Abstract

The accurate O-H bond dissociation enthalpies for a series of meta and para substituted phenols (X-C6H4-OH, X=H, F, Cl, CH3, OCH3, OH, NH2, CF3, CN, and NO2) have been calculated by using the (RO)B3LYP procedure with 6-311G(d,p) and 6-311++G(2df,2p) basis sets. The proton affinities of the corresponding phenoxide ions (XC6H4-O-) have also been computed at the same level of theory. The effect of change of substituent position on the energetics of substituted phenols has been analyzed. The correlations of Hammett’s substituent constants with the bond dissociation enthalpies of the O-H bonds of phenols and proton affinities of phenoxide ions have been explored. View Full-Text
Keywords: Substituted Phenol; Bond Dissociation Energy; Acidity; DFT Substituted Phenol; Bond Dissociation Energy; Acidity; DFT
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Chandra, A.K.; Uchimaru, T. The O-H Bond Dissociation Energies of Substituted Phenols and Proton Affinities of Substituted Phenoxide Ions: A DFT Study. Int. J. Mol. Sci. 2002, 3, 407-422.

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