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Theoretical Study on the Inclusion Interaction of β-Cyclodextrin with Gabapentin and Its Stability.
- Source :
-
Journal of Structural Chemistry . Apr2019, Vol. 60 Issue 4, p564-574. 11p. - Publication Year :
- 2019
-
Abstract
- In this paper, dispersion corrected density functional theory (DFT-D3) with the B3LYP method and the 6–31G(d) basis set is used to study the inclusion processes of gabapentin with β-cyclodextrin and the effect of inclusion on the dehydration condensation reaction of gabapentin. The calculation results show that β-cyclodextrin and gabapentin can form stable inclusion complexes in both vacuum and water. B-β-CDs is the most stable one of four inclusion complexes. After inclusion, the dehydration condensation potential barrier of gabapentin in the β-cyclodextrin cavity is significantly increased. Notably, the reaction barrier of gabapentin in the B-β-CDs complex (a protonated active group of gabapentin with a small mouth of β-cyclodextrin and its hexatomic ring in the cavity of cyclodextrin) even reaches 331.353 kJ/mol in vacuum and 283.538 kJ/mol in water, respectively. There are two obvious increases of 223.574 kJ/mol in vacuum and 193.932 kJ/mol in water after inclusion. Thus, the inclusion complex of β-cyclodextrin with gabapentin, especially B-β-CDs, inhibits the dehydration condensation side-reaction of gabapentin most effectively. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00224766
- Volume :
- 60
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Journal of Structural Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 136256332
- Full Text :
- https://doi.org/10.1134/S0022476619040073