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Ab Initio Study of 4(5)-Methylimidazole in Aqueous Solution

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. A 1997, 101, 42, 7885-7892
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    Ab Initio Study of 4(5)-Methylimidazole in Aqueous Solution
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    Laboratoire de Chimie théorique, URA CNRS 510, Institut Nancéien de Chimie Moléculaire, Université Henri Poincaré-Nancy I, BP 239, 54506 Vandoeuvre-lès-Nancy Cedex, France
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 1997, 101, 42, 7885–7892
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    https://doi.org/10.1021/jp971390n
    Published October 16, 1997
    Copyright © 1997 American Chemical Society
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    Abstract

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    The properties of the two tautomers of 4(5)-methylimidazole in aqueous solution have been studied through theoretical calculations using ab initio methods and various solvent models. We focus this study on the environmental effects due to cooperative solute−solvent interactions. The modifications of the tautomeric equilibrium and pKa value through hydrogen-bond formation and electrostatic solvation effects are discussed. The computations show that the polarizable continuum model of the solvent is able to give reasonable results for these properties. The prediction of absolute values of pKa is difficult, but relative values are reproduced quite well. We also consider a discrete-continuum model for the solution, but we show that this model leads to slightly stable (or unstable) complexes. Our results stress the importance of nonadditive energy contributions, which are presumably fundamental in order to explain the mechanism of several biological processes involving histidine residues.

    Copyright © 1997 American Chemical Society

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    †

     On leave from:  Department of Chemical Physics, University of Science and Technology of China, 230026 Hefei, P. R. China.

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    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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     Abstract published in Advance ACS Abstracts, September 1, 1997.

    Cited By

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    This article is cited by 34 publications.

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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 1997, 101, 42, 7885–7892
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jp971390n
    Published October 16, 1997
    Copyright © 1997 American Chemical Society
    Request reuse permissions

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