Assessment Of The Tautomeric Population Of Benzimidazole Derivatives In Solution: A Simple And Versatile Theoretical-Experimental Approach

Keywords

Bezimidazole; Computational chemistry; Omeprazole; Tautomerism; TDDFT

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. Graphical abstract: 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.[Figure not available: see fulltext.]

Publication Date

1-1-2015

Publication Title

Journal of Computer-Aided Molecular Design

Volume

29

Issue

2

Number of Pages

143-154

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1007/s10822-014-9810-7

Socpus ID

84925538014 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/84925538014

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