Molecules 2009, 14(7), 2656-2668; doi:10.3390/molecules14072656
Article

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

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Received: 29 June 2009; in revised form: 13 July 2009 / Accepted: 17 July 2009 / Published: 22 July 2009
(This article belongs to the Special Issue Macromolecules: Chemistry, Medicinal and Functional Materials)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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[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.
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.

AMA 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(7):2656-2668.

Chicago/Turabian Style

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.

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