Conversion mechanism and isomeric preferences of the cis and trans isomers of anti-cancer medicine carmustine; A double hybrid DFT calculation
| Autor: | Mohammadsaleh Norouzibazaz, Saba Hadidi, Farshad Shiri |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Carmustine
010304 chemical physics Hydrogen bond Chemistry General Physics and Astronomy 010402 general chemistry 01 natural sciences 0104 chemical sciences Solvent Computational chemistry 0103 physical sciences medicine Molecule Density functional theory Physical and Theoretical Chemistry Dispersion (chemistry) Cis–trans isomerism Basis set medicine.drug |
| Zdroj: | Chemical Physics. 522:39-43 |
| ISSN: | 0301-0104 |
| DOI: | 10.1016/j.chemphys.2019.02.013 |
| Popis: | The conversion mechanism of cis and trans isomeric forms of anti-cancer medicine carmustine have been investigated. The density functional theory calculations were carried out utilizing the double-hybrid method of Grimme’s B2PLYP combined with Grimme’s D3BJ dispersion and with the basis set of def2-QZVP. According to the obtained results, the trans carmustine in the gas phase by acquiring 21.00 kcal mol−1 can overcome the nitrosyl rotation activation barrier and convert to the cis isomer. The resulting cis form by releases 2.77 kcal mol−1 of energy for gas phase is more stable than the trans carmustine. Moreover, by applying water as a solvent field, it is clear that water molecules by forming hydrogen bonds with the drug would stabilize the trans form by about 1.30 kcal mol−1. In this situation, the conversion activation barrier reaches to 17.22 kcal mol−1 which is 3.77 kcal mol−1 lower than this value for the gaseous state. |
| Databáze: | OpenAIRE |
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