Quantum chemistry of cocaine and its isomers I: energetics, reactivity and solvation

Abstract: We investigate the rich stereochemistry of cocaine and its diastereoisomers from a theoretical perspective using density func-
tional 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 calcula-
tion 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

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch
• Notes: South African journal of chemistry. - 75 (2021) , 18-27, ISSN: 1996-840X

Contributors, Places and Time

• Event: Veröffentlichung
• (where): Freiburg
• (who): Universität
• (when): 2024
• Creator: Ben Amara, Safa ; Koslowski, Thorsten ; Zaidi, Ali

Further information

• DOI: 10.17159/0379-4350/2021/v75a3
• URN: urn:nbn:de:bsz:25-freidok-2483321
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 2025-08-14T10:54:46+0200