Assessment of the tautomeric population of benzimidazole derivatives in solution: a simple and versatile theoretical-experimental approach
Abbreviated Journal Title
J. Comput.-Aided Mol. Des.
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
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 of Computer-Aided Molecular Design
"Assessment of the tautomeric population of benzimidazole derivatives in solution: a simple and versatile theoretical-experimental approach" (2015). Faculty Bibliography 2010s. 6506.