Acidity of the chlorinated phenols: DFT study and experiential affirmation
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A quantum mechanical density functional theory (DFT) was successfully developed for the estimation of pKa values of chlorinated phenols in aqueous solution with a precision of 0.9 pKa units. The MP2/6-311++G(d,p)//B3LYP/6-31+G(d) level of theory was used for the gas phase calculation. For computation in the solution phase and to calculate the energy difference of the acid–base, the polarized continuum model (PCM) at the HF/6-31G(d,p) level was used. The pKa value was computed for each involved species using pentachlorophenol (PCP) as a reference molecule. Natural bond orbital (NBO) analysis considering the natural resonance theory (NRT) was carried out on an optimized geometry of studied compounds to give information about the nature of bonds.
KeywordsChlorinated phenols DFT calculation Acidity
Support from University of Mohaghegh Ardabili is gratefully acknowledged.
- 2.Shields GC, Seybold PG (2014) Computational approaches for the prediction of pKa values. Taylor & Francis, AbingdonGoogle Scholar
- 17.Bolton PD, Ellis J, Hall FM (1970) Additive substituent effects on the thermodynamic functions of proton ionization processes. Part 111. Phenols with adjacent methyl and chloro-substituents. J Chem Soc B. https://doi.org/10.1039/J29700001252
- 18.Fischer A, Leary GJ, Topsom RD, Vaughan J (1967) Ionic dissociation of 4-substituted 2,6-dichlorophenols. J Chem Soc B. https://doi.org/10.1039/J29670000686
- 19.Fischer A, Leary GJ, Topsom RD, Vaughan J (1966) Ionic dissociation of 4-substituted 2.6-dimethylphenols. J Chem Soc B. https://doi.org/10.1039/J29660000782
- 27.Wavefunction, Inc. (2019) Spartan ‘06V102’. Wavefunction, Inc., IrvineGoogle Scholar