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

doi:10.3390/i3040407

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

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

Asit K. Chandra ¹ and Tadafumi Uchimaru ²

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.

Keywords: Substituted Phenol; Bond Dissociation Energy; Acidity; DFT

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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.

AMA 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. International Journal of Molecular Sciences. 2002; 3(4):407-422.

Chicago/Turabian Style

Chandra, Asit K.; Uchimaru, Tadafumi. 2002. "The O-H Bond Dissociation Energies of Substituted Phenols and Proton Affinities of Substituted Phenoxide Ions: A DFT Study." Int. J. Mol. Sci. 3, no. 4: 407-422.

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