The AIBLHiCoS Method: Predicting Aqueous pKa Values from Gas-Phase Equilibrium Bond Lengths

Journal of Chemical Information and Modeling
Cate AnstöterP L A Popelier

Abstract

The proposed AIBLHiCoS method predicts a given compound's pKa in aqueous solution from a single ab initio bond length only, after geometry optimization in the gas phase. Here we provide simple and predictive equations for naphthols and chemically similar biomolecules. Each linear equation corresponds to a High-Correlation Subset (HiCoS) that expresses the novel type of linear free energy relationship discovered here. The naphthol family exhibits a clear and strong relationship with the phenol family, with the "active" C-O bond always producing the highest correlations. The proposed method can isolate erroneous experiments and operate in non-aqueous solution and at different temperatures. Moreover, the existence of "active fragments" is demonstrated in a variety of sizable biomolecules for which the pKa is successfully predicted.

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Citations

Jun 27, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·M Merced Montero-CampilloJosé Elguero
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jeffrey PlantePaul L A Popelier
Jan 23, 2018·Journal of Chemical Information and Modeling·Haoyu S YuArt D Bochevarov

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