Acidity of the chlorinated phenols: DFT study and experiential affirmation

  • Somayyeh KheirjouEmail author
  • Gholamhassan Imanzadeh
  • Havva Rezaei
  • Nasimeh Safari
Original Paper


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.

Graphical abstract

Chlorinated phenols.


Chlorinated phenols DFT calculation Acidity 



Support from University of Mohaghegh Ardabili is gratefully acknowledged.


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Somayyeh Kheirjou
    • 1
    Email author
  • Gholamhassan Imanzadeh
    • 1
  • Havva Rezaei
    • 1
  • Nasimeh Safari
    • 1
  1. 1.Department of ScienceUniversity of Mohaghegh ArdabiliArdabilIran

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