On the Electronic Structure of Cocaine and its Metabolites

• Type: Article in International Scientific Journal
• Date: 2009

Authors

David A Rincon (Author) Other; Maria Natalia D S Dias Soeiro Cordeiro (Author) FCUP; Ricardo A Mosquera (Author) Other

Journal

Title: Journal of Physical Chemistry A

Vol. 113

Pages: 13937-13942

ISSN: 1089-5639

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 9 Citations

Scopus - 9 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-DJN

DOI: 10.1021/jp9056048

Abstract (EN): This work aims at describing the electronic features of cocaine and how they are modified by the different substituents present in its metabolites. The QTAIM analysis of B3LYP and MP2 electron densities obtained with the 6-311++G** 6d basis set for cocaine and its principal metabolites indicates: (i) its positive charge is shared among the amino hydrogen. those of the methylamino group, and all of the hydrogens attached to the bicycle structure, (ii) the zwitterionic structure of benzoylecgonine can be described as two partial Charges of 0.63 au, the negative one shared by the oxygens of the carboxylate group, whereas the positive charge is distributed among, all the hydrogens that bear the positive charge in cocaine; (iii) its hydrogen bond is strengthened in the derivatives without benzoyloxy group and is also slightly strengthened as the size of the alkyl ester group at position 2 increases.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 6