Computational Study of Inclusion Complex between Omeprazole Enantiomer and β-Cyclodextrin : NBO and RDG Analysis
Atthar Luqman Ivansyah1,*, Enung Siti Nurhidayah2, Citra Deliana Dewi Sundari3, Muhamad A. Martoprawiro4, Buchari2
1Master Program in Computational Science, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Jl.Ganesha No. 10, Bandung, West Java, 40132, Indonesia
2Division of Analytical Chemistry, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Jl. Ganesha No. 10, Bandung, West Java, 40132, Indonesia
3Department of Chemistry Education, UIN Sunan Gunung Djati Bandung, Jl. Cimincrang, Cimenerang, Panyileukan, Bandung, West Java, 40292, Indonesia
4Division of Physical and Inorganic Chemistry, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Jl. Ganesha No. 10, Bandung, West Java, 40132, Indonesia
*corresponding author: atthar[at]compscience.itb.ac.id
Abstract
NBO and RDG analysis of inclusion complex between R/S-omeprazole (OMZ) enantiomer and β-cyclodextrin (CYD) have been carried out to elucidate the interaction between them in order to understand the performance of β-cyclodextrin for the separation of omeprazole enantiomer. NBO analysis results showed that the inclusion complex of R-omeprazole with β-cyclodextrin is more stable than the inclusion complex of S-omeprazole with β-cyclodextrin, in which the total value of the stabilization energy (E(2)) caused by hydrogen bonding in the inclusion complex of R-omeprazole with β-cyclodextrin is 150.22 kcal/mol and in the inclusion complex of S-omeprazole with β-cyclodextrin is 115.62 kcal/mol. From RDG analysis results, beside hydrogen bonding, there are also Van der Waals interaction and steric effect on the interaction between omeprazole enantiomer and β-cyclodextrin.
Keywords: NBO, RDG, inclusion complex, enantiomer, omeprazole, β-cyclodextrin.
Topic: Chemistry