J.B. Bhagyasree et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 102 (2013) 99–113
113
for n2(O27) ? rꢀ (NAO) and n2(O30) ? rꢀ (NAO) interaction in the
molecule. Overall, the TD-DFT calculations on the molecule pro-
vided deep insight into their electronic structures and properties.
In addition, the calculated 1H NMR and UV–Vis results are all in
good agreement with the experimental data .The lowering of
HOMO–LUMO band gap supports bioactive property of the mole-
cule. MEP predicts the most reactive part in the molecule. The cal-
culated first hyperpolarizability is comparable with the reported
values of similar derivatives and is an attractive object for future
studies of nonlinear optics.
[28] Roy Dennington, Todd Keith, John Millam, GaussView, Version 5, Semichem
Inc., Shawnee Mission KS, 2009.
[29] J.M.L. Martin, C. Van Alsenoy, GAR2PED, A Program to Obtain a Potential
Energy Distribution from a Gaussian Archive Record, University of Antwerp,
Belgium, 2007.
[30] N.P.G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of
Organic Structures, Wiley, New York, 1994.
[31] R.M. Silverstein, F.X. Webster, Spectrometric Identification of Organic
Compounds, sixth ed., John Wiley, Asia, 2003.
[32] A. Perjessy, D. Rasala, P. Tomasik, R. Gawinecki, Collect. Czech. Chem.
Commun. 50 (1985) 2443–2452.
[33] J.F. Brown Jr., J. Am. Chem. Soc. 77 (1955) 6341–6351.
[34] J.H.S. Green, W. Kynanston, A.S. Lindsey, Spectrochim. Acta 17 (1961) 486–
502.
[35] O. Exner, S. Kovac, E. Solcaniova, Collect. Czech. Chem. Commun. 37 (1972)
2156–2168.
Acknowledgment
[36] G. Varsanyi, E. Molner-Pall, K. Kosa, G. Keresztury, Acta Chim. Acad. Sci. Hung.
106 (1979) 481–498.
[37] V. Suryanarayana, A.P. Kumar, G.R. Rao, G.C. Panday, Spectrochim. Acta 48A
(1992) 1481–1489.
The authors are thankful to University of Antwerp for access to
University’s CalcUA supercomputer cluster.
[38] R. Saxena, L.D. Kaudpal, G.N. Mathur, J. Polym. Sci. Part A: Polym. Chem. 40
(2002) 3959–3966.
Appendix A. Supplementary material
[39] R.M. Silverstein, G.C. Bassler, T.C. Morril, Spectrometric Identification of
Organic Compounds, 5th ed., John Wiley and Sons Inc., Singapore, 1991.
[40] K. Nakamoto, Infrared and Raman Spectrum of Inorganic and coordination
Compounds, 5th ed., John Wiley and Sons, Inc., New York, 1997.
[41] T.D. Klots, W.B. Collier, Spectrochim. Acta 51A (1995) 1291–1316.
[42] N.B. Colthup, L.H. Daly, S.E. Wiberly, Introduction to Infrared and Raman
Spectroscopy, 3rd ed., Academic Press, Boston, 1990.
[43] A. Bigotto, B. Pergolese, J. Raman Spectrosc. 32 (2001) 953–959.
[44] N. Sandhyarani, G. Skanth, S. Berchmanns, V. Yegnaraman, T. Pradeep, J. Colloid
Interface Sci. 209 (1999) 154–161.
[45] J. Coates, in: R.A. Meyers (Ed.), Encyclopedia of Analytical Chemistry;
Interpretation of Infrared Spectra. A Practical Approach, John Wiley and Sons
Ltd., Chichester, 2000.
[46] P. Sett, N. Paul, S. Chattopadhyay, P.K. Mallick, J. Raman Spectrosc. 30 (1999)
277–287.
Supplementary data associated with this article can be found, in
References
[1] A.D. Rodrıguez, C. Ramırez, I.I. Rodrıguez, E. Gonzalez, Org. Lett. 1 (1999) 527–
530.
[2] M. Prudhomme, J. Guyot, G. Jeminet, J. Antibiot. 39 (1986) 934–937.
[3] S.M. Rida, F.A. Ashour, S.A.M. El-Hawash, M.M. ElSemary, M.H. Badr, M.A.
Shalaby, Eur. J. Med. Chem. 40 (2005) 949–959.
[4] I. Yildiz-Oren, I. Yalcin, E. Aki-Sener, N. Ucarturk, Eur. J. Med. Chem. 39 (2004)
291–298.
[47] P. Sett, S. Chattopadhyay, P.K. Mallick, Spectrochim. Acta 56A (2000) 855–875.
[48] P. Sett, S. Chattopadhyay, P.K. Mallick, J. Raman Spectrosc. 31 (2000) 177–184.
[49] V. Volvosek, G. Baranovic, L. Colombo, J.R. Durig, J Raman Spectrosc. 22 (1991)
35–41.
[50] M. Muniz-Miranda, E. Castelluci, N. Neto, G. Sbrena, Spectrochim. Acta 39A
(1983) 107–113.
[51] J.H.S. Green, Spectrochim. Acta 24 (1968) 1627–1637.
[52] G. Varsanyi, Assignments of Vibrational Spectra of Seven Hundred Benzene
Derivatives, Wiley, New York, 1974.
[53] V.S. Madhavan, H.T. Varghese, S. Mathew, J. Vinsova, C.Y. Panicker,
Spectrochim. Acta 72A (2009) 547–553.
[54] C.Y. Panicker, H.T. Varghese, K.R. Ambujakshan, S. Mathew, S. Ganguli, A.K.
Nanda, C. Van Alsenoy, Y.S. Mary, J. Mol. Struct. 963 (2010) 137–144.
[55] G. Socrates, Infrared Characteristic Group Frequencies, Wiley-Interscience,
New York, 1980.
[56] W. KunYi, C.W. Park, M.S. Kim, K. Kim, Bull. Korean Chem. Soc. 8 (1987) 291–
296.
[57] W.B. Collier, T.D. Klots, Spectrochim. Acta 51A (1995) 1255–1272.
[58] G. Smith, D.E. Lynch, K.A. Byriel, C.H.L. Kennard, Aust. J. Chem. 48 (1995) 1133–
1149.
[59] R.D. Chambers, M.A. Fox, G. Sandford, J. Trmcic, A. Goeta, J. Fluorine Chem. 128
(2007) 29–33.
[60] N. Okabe, T. Nakamura, H. Pukuda, Acta Crystallogr. C49 (1993) 1678–1680.
[61] N. Sundaraganesan, S. Ayyappan, H. Umamaheswari, B.D. Joshua, Spectrochim.
Acta 66A (2007) 17–27.
[62] P. Purkayastha, N. Chattopadhyay, Phys. Chem. Chem. Phys. 2 (2003) 203–210.
[63] A. Lifshitz, C. Tamburu, A. Suslensky, F. Dubnikova, J. Phys. Chem. A 110 (2006)
4607–4613.
[64] Y.S. Mary, H.T. Varghese, C.Y. Panicker, T. Ertan, I. Yildiz, O. Temiz-Arpaci,
Spectrochim. Acta 71A (2008) 566–571.
[65] A. Saeed, S. Hussain, U. Florke, Turk. J. Chem. 32 (2008) 481–486.
[66] Y.R. Shen, The Principles of Nonlinear Optics, Wiley, New York, 1984.
[67] P.V. Kolinsky, Opt. Eng. 31 (1992) 11676–11684.
[5] I. Yildiz-Oren, B. Tekiner-Gulbas, I. Yalcin, O. Temiz-Arpaci, E. Aki- Sener, N.
Altanlar, Arch. Pharm. 337 (2004) 402–410.
[6] O. Temiz-Arpaci, A. Ozdemir, I. Yalcin, I. Yildiz, E. Aki-Sener, N. Altanlar, Arch.
Pharm. 338 (2005) 105–111.
[7] A. Akbay, I. Oren, O. Temiz-Arpaci, E. Aki-Sener, I. Yalcin, Arzneim. Forsch. 53
(2003) 266–272.
[8] R.K. Plemper, K.J. Erlandson, A.S. Lakdawala, A. Sun, A. Prussia, J. Boonsombat,
E. Aki-Sener, I. Yalcin, I. Yildiz, O. Temiz-Arpaci, B.P. Tekiner, D. Liotta, J.P.
Snyder, Proc. Natl. Acad. Sci. USA 101 (2004) 5628–5634.
[9] H. Lage, E. Aki-Sener, I. Yalcin, Int. J. Cancer 119 (2006) 213–220.
[10] A. Pınar, P. Yurdakul, I. Yildiz, O. Temiz-Arpaci, N.L. Acan, E. Aki-Sener, I. Yalcin,
Biochem. Biophys. Res. Commun. 317 (2004) 670–674.
[11] O. Temiz-Arpaci, B. Tekiner-Gulbas, I. Yildiz, E. Aki-Sener, I. Yalcin, Bioorg.
Med. Chem. 13 (2005) 6354–6359.
[12] B. Tekiner-Gulbas, O. Temiz-Arpaci, I. Yildiz, E. Aki-Sener, I. Yalcin, SAR QSAR
Environ. Res. 17 (2006) 121–132.
[13] W.D. Dunwell, D. Evans, J. Med. Chem. 20 (1977) 797–801.
[14] Farbenfabriken, A.G. Bayer, Netherlands Patent 6505511, 1965.
[15] I. Yalcin, E. Sener, S. Ozden, A. Akin, S. Yildiz, J. Pharm. Sci. 11 (1986) 257–269.
[16] E. Sener, S. Ozden, I. Yalcin, T. Ozden, A. Akin, S. Yildiz, J. Pharm. Sci. 11 (1986)
190–202.
[17] S. Ozden, T. Ozden, E. Sener, A. Akin, S. Yildiz, J. Pharm. Sci. 12 (1987) 39–47.
[18] E. Sener, I. Yalcin, S. Ozden, T. Ozden, A. Akin, S. Yildiz, J. Med. Pharm. 11 (1987)
391–396.
[19] P.L. Anto, C.Y. Panicker, H.T. Varghese, D. Philip, O. Temiz-Arpaci, B. Tekiner-
Gulbas, I. Yildiz, Spectrochim. Acta 67A (2007) 744–749.
[20] K.R. Ambujakshan, V.S. Madhavan, H.T. Varghese, C.Y. Panicker, O. Temiz-
Arpaci, B. Tekiner-Gulbas, I. Yildiz, Spectrochim. Acta 69A (2008) 782–788.
[21] N. Noyanalpan, E. Sener, FABAD J. Pharm. Sci. 11 (1986) 111–119.
[22] E. Sener, I. Yalcin, A. Akin, N. Noyanalpan, J. Fac. Pharm. Gazi. 4 (1987) 1–9.
[23] I. Yalcin, E. Sener, T. Ozden, S. Ozden, A. Akin, Eur. J. Med. Chem. 25 (1990)
705–708.
[24] M.J. 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.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro,
M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, 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, D.J. Fox, Gaussian 09, Revision B.01,
Gaussian, Inc., Wallingford CT, 2010.
[68] D.F. Eaton, Science 25 (1991) 281–287.
[69] D.A. Kleinman, Phys. Rev. 126 (1962) 1977–1979.
[70] L.N. Kuleshova, M.Y. Antipin, V.N. Khrustalev, D.V. Gusev, E.S. Bobrikova,
Kristallografiya 48 (2003) 594–601.
[71] M. Adant, L. Dupuis, L. Bredas, Int. J. Quantum. Chem. 56 (2004) 497–507.
[72] E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, NBO Version 3.1,
Gaussian Inc., Pittsburgh, PA.
[73] J. Choo, S. Kim, H. Joo, Y. Kwon, J. Mol. Struct. (Theochem.) 587 (2002) 1–8.
[74] R.S. Mulliken, J. Chem. Phys. 23 (1955) 1833–1840.
[75] K. Wolinski, J.F. Hinton, P. Pulay, J. Am. Chem. Soc. 112 (1990) 8251–8260.
[76] E. Scrocco, J. Tomasi, Adv. Quantum. Chem. 11 (1978) 115–193.
[77] F.J. Luque, J.M. Lopez, M. Orozco, Theor. Chem. Acc. 103 (2000) 343–345.
[78] P. Politzer, J.S. Murray, in: D.L. Beveridge, R. Lavery (Eds.), Theoretical
Biochemistry and Molecular Biophysics: A Comprehensive Survey. Protein,
vol. 2, Adenine Press, Schenectady, NY, 1991 (Chapter 13).
[79] E. Scrocco, J. Tomasi, Curr. Chem. 7 (1973) 95–170.
[25] J.B. Foresman, in: E. Frisch (Ed.), Exploring Chemistry with Electronic Structure
Methods: A Guide to Using Gaussian, Gaussian, Inc., Pittsburg, PA, 1996.
[26] P.J. Hay, W.R. Wadt, J. Chem. Phys. 82 (1985) 270–283.
[27] J.Y. Zhao, Y. Zhang, L.G. Zhu, J. Mol. Struct. Theochem. 671 (2004) 179–187.