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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; in revised form: 13 July 2009 / Accepted: 17 July 2009 / Published: 22 July 2009
Abstract: 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 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.
Keywords: azide; azidothymidine; electronic structures; density functional theory
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MDPI and ACS Style
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.
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(7):2656-2668.
Chen, Fang-Fang; Wang, Feng. 2009. "Electronic Structure of the Azide Group in 3¢-Azido-3¢-deoxythymidine (AZT) Compared to Small Azide Compounds." Molecules 14, no. 7: 2656-2668.