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Molecules 2009, 14(7), 2656-2668;

Electronic Structure of the Azide Group in 3¢-Azido-3¢-deoxythymidine (AZT) Compared to Small Azide Compounds

Centre for Molecular Simulation, Swinburne University of Technology, P. O. Box 218, Hawthorn, Melbourne, Victoria, 3122, Australia
Author to whom correspondence should be addressed.
Received: 29 June 2009 / Revised: 13 July 2009 / Accepted: 17 July 2009 / Published: 22 July 2009
(This article belongs to the Special Issue Macromolecules: Chemistry, Medicinal and Functional Materials)
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Theoretical calculations for some structural and electronic properties of the azide moiety in the nucleoside reverse transcriptase (RT) inhibitor 3¢-azido-3¢-deoxythymidine (AZT) are reported. These properties, which include geometrical properties in three dimensional space, Hirshfeld charges, electrostatic potential (MEP), vibrational frequencies, and core and valence ionization spectra, are employed to study how the azide group is affected by the presence of a larger fragment. For this purpose, two small but important organic azides, hydrazoic acid and methyl azide, are also considered. The general features of trans Cs configuration for RNNN fragments[1] is distorted in the large AZT bio-molecule. Hirshfeld charge analysis shows charges are reallocated more evenly on azide when the donor group R is not a single atom. Infrared and photoelectron spectra reveal different aspects of the compounds. In conclusion, the electronic structural properties of the compounds depend on the specific property, the local structure and chemical environment of a species. View Full-Text
Keywords: azide; azidothymidine; electronic structures; density functional theory azide; azidothymidine; electronic structures; density functional theory

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Chen, F.-F.; Wang, F. Electronic Structure of the Azide Group in 3¢-Azido-3¢-deoxythymidine (AZT) Compared to Small Azide Compounds. Molecules 2009, 14, 2656-2668.

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