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Accurate pKa Calculation of the Conjugate Acids of Alkanolamines, Alkaloids and Nucleotide Bases by Quantum Chemical Methods

Authors

  • Satesh Gangarapu,

    1. Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen (The Netherlands)
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  • Dr. Antonius T. M. Marcelis,

    1. Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen (The Netherlands)
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  • Prof. Han Zuilhof

    Corresponding author
    1. Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen (The Netherlands)
    2. Department of Chemical and Materials Engineering, King Abdulaziz University, Jeddah (Saudi Arabia)
    • Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen (The Netherlands)
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Abstract

The pKa of the conjugate acids of alkanolamines, neurotransmitters, alkaloid drugs and nucleotide bases are calculated with density functional methods (B3LYP, M08-HX and M11-L) and ab initio methods (SCS-MP2, G3). Implicit solvent effects are included with a conductor-like polarizable continuum model (CPCM) and universal solvation models (SMD, SM8). G3, SCS-MP2 and M11-L methods coupled with SMD and SM8 solvation models perform well for alkanolamines with mean unsigned errors below 0.20 pKa units, in all cases. Extending this method to the pKa calculation of 35 nitrogen-containing compounds spanning 12 pKa units showed an excellent correlation between experimental and computational pKa values of these 35 amines with the computationally low-cost SM8/M11-L density functional approach.

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