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E-Journal of Chemistry
Volume 9, Issue 4, Pages 2191-2204
http://dx.doi.org/10.1155/2012/895240

Structural and Theoretical Studies of 2-amino-3-nitropyridine

1Chemistry Department, Faculty of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia
2Chemistry Department, Faculty of Science, Assiut Uniersity, Assiut 71516, Egypt
3Natural Sciences Department, Riyadh Community College, King Saud University, PO Box 28095, Riyadh 11437, Saudi Arabia
4Laboratoire de Chimie des Matériaux,, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia

Received 2 November 2011; Accepted 7 January 2012

Copyright © 2012 Hindawi Publishing Corporation. 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

Geometrical optimization, spectroscopic analysis, electronic structure and nuclear magnetic resonance of 2-amino-3-nitropyridine (ANP) were investigated by utilizing ab-initio (MP2) and DFT(B3LYP) using 6-311++G(d,p) basis set. Geometrical parameters (bond lengths, bond angles and torsion angles) were computed and compared with the experimental values obtained using X-ray single crystal measurements of the title compound. IR spectra were obtained and assigned by vibrational analysis. Comparing the theoretically calculated values (bond lengths, bond and dihedral angles) using both B3LYP/6-311++G(d,p) and MP2/6-311++G(d,p) methods of calculations with the experimentally determined data by X-ray single crystal measurements, all the data obtained in this investigation were considered to be reliable. The theoretical infrared spectra have been successfully simulated by means of DFT and MP2 levels of calculations. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of 2-amino-3-nitropyridine were calculated using the GIAO method in DMSO solution using IEF-PCM model and compared with the experimental data. Intramolecular hydrogen bonding interaction in this compound was investigated by means of the NBO analysis. The calculated HOMO and LUMO energies show that charge transfer occurs within the molecule.