Assessment of the tautomeric population of benzimidazole derivatives in solution: a simple and versatile theoretical-experimental approach

    Authors

    C. Diaz; L. Llovera; L. Echevarria;F. E. Hernandez

    Comments

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    Abbreviated Journal Title

    J. Comput.-Aided Mol. Des.

    Keywords

    Computational chemistry; TDDFT; Tautomerism; Bezimidazole; Omeprazole; EXACT EXCHANGE; DENSITY; OMEPRAZOLE; THERMOCHEMISTRY; MOLECULES; MODELS; STATES; C-13; DNA; Biochemistry & Molecular Biology; Biophysics; Computer Science, ; Interdisciplinary Applications

    Abstract

    Herein, we present a simple and versatile theoretical-experimental approach to assess the tautomeric distribution on 5(6)-aminobenzimidazole (5(6)-ABZ) derivatives in solution via one-photon absorption. The method is based on the optimized weighted sum of the theoretical spectra of the corresponding tautomers. In this article we show how the choice of exchange-correlation functional (XCF) employed in the calculations becomes crucial for the success of the approach. After the systematic analysis of XCFs with different amounts of exact-exchange we found a better performance for B3LYP and PBE0. The direct test of the proposed method on omeprazole, a well-known 5(6)-benzimidazole based pharmacotherapeutic, demonstrate its broader applicability. The proposed approach is expected to find direct applications on the tautomeric analysis of other molecular systems exhibiting similar tautomeric equilibria. Using a weighted sum of the corresponding individual tautomer theoretical spectra, the tautomeric population of benzimidazole derivatives in solution and at room temperature is directly determined through the theoretical-experimental fitting of the UV-Vis spectra of the tautomeric mixture at equilibrium. The reliability of the proposed method is based on the existent spectral difference between the two species.

    Journal Title

    Journal of Computer-Aided Molecular Design

    Volume

    29

    Issue/Number

    2

    Publication Date

    1-1-2015

    Document Type

    Article

    Language

    English

    First Page

    143

    Last Page

    154

    WOS Identifier

    WOS:000348190700004

    ISSN

    0920-654X

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