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
Copyright Status
Unknown
Socpus ID
84925538014 (Scopus)
Source API URL
https://api.elsevier.com/content/abstract/scopus_id/84925538014
STARS Citation
Diaz, Carlos; Llovera, Ligia; Echevarria, Lorenzo; and Hernández, Florencio E., "Assessment Of The Tautomeric Population Of Benzimidazole Derivatives In Solution: A Simple And Versatile Theoretical-Experimental Approach" (2015). Scopus Export 2015-2019. 343.
https://stars.library.ucf.edu/scopus2015/343