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Computational and Spectral Studies of Nimesulide Impurity D: 4-Nitro-2-phenoxy Aniline
Corresponding Author(s) : B.L. Bhaskar
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
The present work describes the structural and spectral characterization studies of 4-nitro-2-phenoxy aniline, which is an intermediate product during the synthesis of nimesulide, by both computational and experimental methods. Characteristic IR absorption frequencies were computed by Gaussian 03 using density function methods at B3LYP/6-311G, B3LYP/6-31G basis sets and Hartree Fock methods at HF 3-21G basis set. Theoretical XRD data was generated by Gaussian 03 at different basis sets and data consolidated to show concordance with experimental data available in the literature and also corroborate the presence of intra-molecular hydrogen bonding. The HOMO and LUMO energy gap value has been computed to be around 4 eV indicating relatively high reactivity of the compound. In general, computational and experimental data showed satisfactory concurrence with each other.
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References
G.G.L. Moore and J.K. Harrington, US Patent No. 3840597 (1974).
A. Prasad, M.L. Sharma, S. Kanwar, R. Rathee, S.D. Sharma, J. Sci. Ind. Res., 64,756 (2005).
H.R. Manjunath, M.T. Shreenivasa, M. Mahendra, T.M. Mohan Kumar, B.E. Kumaraswamy and M.A. Sridhar, Acta Crystallogr., 66E, 1255 (2010); doi:10.1107/S1600536810012237.
M.T. Shreenivasa, B.P. Chetan and A.R. Bhat, J. Pharm. Sci. Technol., 1, 88 (2009).
E.C. Nicolas and T.H. Scholz, J. Pharm. Biomed. Anal., 16, 813 (1998); doi:10.1016/S0731-7085(97)00131-3.
C.K. Zacharis and P.D. Tzanavaras, Chromatographia, 73, 347 (2011); doi:10.1007/s10337-010-1876-3.
B. Tubic, B. Ivkovic, M. Zecevic and S. Vladimirov, Acta Chim. Slov., 54, 583 (2007).
M. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.R.Montgomery Jr, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian Inc., Wallingford, CT (2009).
M.M. El-Nahass, M.A. Kamel, A.A. El-Barbary, M.A.M. El-Mansy and M. Ibrahim, Spectrochim. Acta A, 111, 37 (2013); doi:10.1016/j.saa.2013.03.072.
A.D. Becke, Phys. Rev. A, 38, 3098 (1988); doi:10.1103/PhysRevA.38.3098.
A.D. Becke, J. Chem. Phys., 98, 5648 (1993); doi:10.1063/1.464913.
B.G. Johnson and M.J. Frisch, Chem. Phys. Lett., 216, 133 (1993); doi:10.1016/0009-2614(93)E1238-C.
C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988); doi:10.1103/PhysRevB.37.785.
V. Arjunan, P.S. Balamourougane, C.V. Mythili and S. Mohan, J. Mol. Struct., 1003, 92 (2011); doi:10.1016/j.molstruc.2011.07.043.
T. Prabhu, S. Periandy and S. Mohan, Spectrochim. Acta A, 78, 566 (2011); doi:10.1016/j.saa.2010.11.024.
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.
S. Qiu, L. Liu, X. Jin, A. Zhang, K. Wu and L. Wang, Spectrochim. Acta A, 77, 572 (2010); doi:10.1016/j.saa.2010.05.012.
V. Arjunan, P. Ravindran, T. Rani and S. Mohan, J. Mol. Struct., 988, 91 (2011); doi:10.1016/j.molstruc.2010.12.032.