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Blue shifted intramolecular C-H dot operator dot operator dot operator improper hydrogen bonds in conformers of zidovudine
List of Titles
Blue shifted intramolecular C-H dot operator dot operator dot operator improper hydrogen bonds in conformers of zidovudine
Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.3/88219
- Title
- Blue shifted intramolecular C-H dot operator dot operator dot operator improper hydrogen bonds in conformers of zidovudine
- Author(s)
- Chen, Fangfang; Selvam, Lalitha; Wang, Feng
- Abstract
- Blue shifted C–H stretch vibrations caused by C–H···O intramolecular improper hydrogen bonds in zidovudine (or AZT) conformers are employed to differentiate its conformers. Two sugar–sugar C–H···O(5′) improper hydrogen bonds, existing in conformers of AZT with apparent drug potency, are related to their unique sugar puckering, showing C(3′)-exo or -endo orientations. Aqueous solution causes a global red shift in IR spectra, but remains reduced blue shifted C–H stretch frequencies. Molecular electrostatic potentials (MEPs) of the conformers and orbitals such as 40a of AZT-B and 37a of AZT-C, which are found to be responsible for the intramolecular improper hydrogen bonds, are also given in this study.
- Publication type
- Journal article
- Research centre
- Swinburne University of Technology. Faculty of Information and Communication Technologies. Centre for Molecular Simulation
- Source
- Chemical Physics Letters, Vol. 493, no. 4-6 (Jun 2010), pp. 358-363
- Publication year
- 2010
- FOR Code(s)
- 0202 Atomic, Molecular, Nuclear, Particle and Plasma Physics; 0306 Physical Chemistry (Incl. Structural); 1007 Nanotechnology
- Keyword(s)
- Blue shifted C-H stretch vibrations; Hydrogen bonds; Zidovudine
- Publisher
- Elsevier
- ISSN
- 0009-2614
- Publisher URL
- http://dx.doi.org/10.1016/j.cplett.2010.05.057
- Copyright
- Copyright © 2010.
- Additional information
- The authors acknowledge support from the Postgraduate Research Award from the Faculty of ICT in Swinburne University of Technology, the Swinburne University Postgraduate Research Award (SUPRA), an award under the Merit Allocation Scheme at the National Computational Infrastructure (NCI) at the Australian National University and Swinburne University Supercomputing Facilities.
- Peer reviewed
