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

    Authors: contact us about adding a copy of your work at [email protected]

    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

    Share

    COinS
     

    Accessibility Statement

    This item was created or digitized prior to April 24, 2027, or is a reproduction of legacy media created before that date. It is preserved in its original, unmodified state specifically for research, reference, or historical recordkeeping. In accordance with the ADA Title II Final Rule, the University Libraries provides accessible versions of archival materials upon request. To request an accommodation for this item, please submit an accessibility request form.