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Estimating hydrogen bond energies: comparison of methods

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Abstract

Hydrogen bonds are among the most important non-bonded interactions found in molecules. Different methods of estimating the strength of hydrogen bonds have been proposed to date. In this work, we present a comparison between methods of estimating hydrogen bond energies that are based on several electron density descriptors based on the quantum theory of atoms in molecules, the natural bond orbital theory, and Mulliken population analysis. The results indicate that the most powerful approach is based on the quantum theory of atoms in molecules, followed by the one employing the natural bond orbital theory. The Mulliken population analysis performed very poorly. The effect of including dispersion correction was also studied. Parameters for predicting hydrogen bond energies are presented.

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Acknowledgments

M.K. thanks the Natural Sciences and Engineering Research Council (NSERC) for continuing support. J.T. appreciates the support of the Allard Foundation, NSERC, and the Canadian Breast Cancer Foundation. This research has been enabled by the use of computing resources provided by WestGrid and Compute/Calcul Canada as well as the PharmaMatrix Cluster.

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Authors and Affiliations

  1. Department of Chemistry, University of Alberta, Edmonton, AB, Canada

    Ahmed T. Ayoub & Mariusz Klobukowski

  2. Department of Physics, University of Alberta, Edmonton, AB, Canada

    Jack Tuszynski

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  1. Ahmed T. Ayoub
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  2. Jack Tuszynski
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  3. Mariusz Klobukowski
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Corresponding author

Correspondence to Mariusz Klobukowski.

Electronic supplementary material

Below is the link to the electronic supplementary material.

214_2014_1520_MOESM1_ESM.pdf

Tables showing the hydrogen bond energies as well as the values of the different descriptors for all hydrogen-bonded systems are shown in Supplementary Material. The coordinates of all the minimized structures are shown as well. (pdf 93 KB)

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Ayoub, A.T., Tuszynski, J. & Klobukowski, M. Estimating hydrogen bond energies: comparison of methods. Theor Chem Acc 133, 1520 (2014). https://doi.org/10.1007/s00214-014-1520-7

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  • DOI: https://doi.org/10.1007/s00214-014-1520-7

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