SciELO - Scientific Electronic Library Online

 
vol.75Evaluation of Bitter Kola Leaf Extract as an Anticorrosion Additive for Mild Steel in 1.2 M H2SO4 ElectrolyteStudy of 'Fingerprints' for Green Tea from Different Planting Areas in Eastern China author indexsubject indexarticles search
Home Pagealphabetic serial listing  

Services on Demand

Article

Indicators

Related links

  • On index processCited by Google
  • On index processSimilars in Google

Share


South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

Abstract

AMARA, Safa Ben; KOSLOWSKI, Thorsten  and  ZAIDI, Ali. Quantum Chemistry of Cocaine and its Isomers I: Energetics, Reactivity and Solvation. S.Afr.j.chem. (Online) [online]. 2021, vol.75, pp.18-27. ISSN 1996-840X.  http://dx.doi.org/10.17159/0379-4350/2021/v75a3.

We investigate the rich stereochemistry of cocaine and its diastereoisomers from a theoretical perspective using density functional theory. The relative stability of the eight considered isomers is discussed, and a comparison of the corresponding internal coordinates is given. Our results reveal that the S-pseudococaine isomer is the most stable conformation, whereas the natural occurring isomer (R-cocaine) lies higher in energy. The different isomers' chemical reactivity is discussed based on the calculation of the hardness, softness, electrophilicity and dipole moment. It was found that the dipole moment varies over a broad range from 0.65 to 4.60 D, whereas the other properties are slightly modified. The solvent effect on the energy stability of the cocaine isomers was studied by considering chloroform, dimethyl-sulfoxide (DMSO) and water as implicit solvents. Our calculations show that the different isomers' energy order and their energy gaps are slightly modified due to solvent effects. However, in all cases, the S-pseudococaine remains the most stable isomer. However, the dipole moment and the chemical reactivity of the cocaine isomers increase with the solvent polarity.

Keywords : Cocaine isomers; DFT; stability; solvent effect; chemical reactivity.

        · text in English     · English ( pdf )

 

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License