A refined model for prediction of hydrogen bond acidity and basicity parameters from quantum chemical molecular descriptors

Literature Information

Publication Date 2009-01-19
DOI 10.1039/B816321A
Impact Factor 3.676
Authors

Mike Devereux, Paul L. A. Popelier, Iain M. McLay


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Abstract

Abraham’s H-bonding parameters αH2 and βH2 have been described in terms of a minimal set of readily obtainable molecular descriptors. These parameters are basically equilibrium constants for complexation of acids with a reference base (αH2) or bases with a reference acid (βH2) measured in a non-hydrogen bonding solvent such as tetrachloromethane. The models were developed using partial least squares with a diverse dataset recently compiled by Platts et al., encompassing a wide range of hydrogen bond acids and bases in order to give a robust model. Although less accurate than the model of Platts et al. the descriptors used in this work avoid expensive supermolecule calculations, and allow prediction of hydrogen bonding characteristics from the isolated molecular wave function. These descriptors can then be generated for a large number of compounds, making them ideal for storage in a quantum isostere database (QID), the construction of which we initiated. The QID is a web-based tool developed to predict bioisosteric replacements in lead optimisation projects. The current descriptors provide hydrogen bonding characteristics of molecules of interest.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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