Structural and Spectroscopic Characterization of 1-(5-Bromothiophen-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one: An Analysis of Electronic and NLO Properties

• Authors: Ö. Tamer , D. Avcı , Y. Atalay
• Languages of publication: EN

Abstracts

EN

The molecular structure of 1-(5-bromothiophen-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one with C_{13}H_8BrNO_3S empirical formula was simulated using B3LYP and CAM-B3LYP levels of density functional theory. After BTNP was optimized on the ground state, its characterization was enhanced via IR, NMR and UV-vis spectroscopies. Conformational analysis was performed based on B3LYP level so as to find the stable conformers of BTNP. Electronic transitions were calculated, and the important contributions from the molecular orbitals to the electronic transitions were investigated. HOMO and LUMO energies were calculated, and obtained energies displayed that charge transfer occurs in BTNP. It was displayed that BTNP is an efficient NLO material due to the coplanar of phenyl-nitro group and carbonyl group. NBO analysis also proved that charge transfer, conjugative interactions and intramolecular hydrogen bonding interactions occur through BTNP.

Keywords

EN

31.15.E-; 33.20.Ea; 33.20.Lg; 42.65.-k; 67.80.Jd

Discipline

• 33.20.Lg: Ultraviolet spectra
• 31.15.E-: Density-functional theory
• 33.20.Ea: Infrared spectra
• 42.65.-k: Nonlinear optics

• Journal: Acta Physica Polonica A
• Year: 2014
• Volume: 126
• Issue: 3
• Pages: 679-688

Dates

published

2014-08

received

2013-07-22

(unknown)

2014-03-09

Contributors

author

Ö. Tamer

• Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey

author

D. Avcı

• Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey

author

Y. Atalay

• Sakarya University, Faculty of Arts and Sciences, Department of Physics, 54187, Sakarya, Turkey

References

• [1] P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York 1991
• [2] H.R. Nalwa, S. Miyata, Nonlinear Optics of Organic Molecules and Polymers, CRC Press, Boca Raton, FL 1997
• [3] S.R. Marder, J.E. Sohn, G.D. Stucky, in: ACS Symp. Series 455, American Chemical Society, Washington 1991
• [4] O. Keller, Nonlinear Optics in Solids, in: Proc. Int. Summer School, Springer, Berlin 1990
• [5] H. Pir, N. Gunay, D. Avcı, Y. Atalay, Spectrochim. Acta A 96, 916 (2012), doi: 10.1016/j.saa.2012.07.044
• [6] H. Pir, N. Gunay, Ö. Tamer, D. Avcı, Y. Atalay, Spectrochim. Acta A 112, 331 (2013), doi: 10.1016/j.saa.2013.04.063
• [7] A. Abbotto, L. Beverina, N. Manfredi, G.A. Pagani, G. Archetti, H.G. Kuball, C. Wittenburg, J. Heck, J. Holtmann, Chem. Eur. J. 15, 6175 (2009), doi: 10.1002/chem.200900287
• [8] J.A. Davies, A. Elangovan, P.A. Sullivan, B.C. Olbricht, D.H. Bale, T.R. Ewy, C.M. Isborn, B.E. Eichinger, B.H. Robinson, P.J. Reid, X. Li, L.R. Dalton, J. Am. Chem. Soc. 130, 10565 (2008), doi: 10.1021/ja8007424
• [9] E.M. Breitung, C.-F. Shu, R.J. McMahon, J. Am. Chem. Soc. 122, 1154 (2000), doi: 10.1021/ja9930364
• [10] I.D.L. Albert, T.J. Marks, M.A. Ratner, J. Am. Chem. Soc. 119, 6575 (1997), doi: 10.1021/ja962968u
• [11] A.N. Prabhu, A. Jayarama, K. Subrahmanya Bhat, V. Upadhyaya, J. Mol. Struct. 1031, 79 (2013), doi: 10.1016/j.molstruc.2012.06.057
• [12] 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.I. Shida, 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, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. 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, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford CT, 2009
• [13] R. Dennington, T. Keith, J. Millam, Semichem Inc., Shawnee Mission KS, GaussView, Version 5 (2009)
• [14] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988), doi: 10.1103/PhysRevB.37.785
• [15] A.D. Becke, J. Chem. Phys. 98, 5648 (1993), doi: 10.1063/1.464913
• [16] T. Yanai, D. Tew, N. Handy, Chem. Phys. Lett. 393, 51 (2004), doi: 10.1016/j.cplett.2004.06.011
• [17] M.J. Frisch, J.A. Pople, J.S. Binkley, J. Chem. Phys. 80, 3265 (1984), doi: 10.1063/1.447079
• [18] S.I. Gorelsky, A.B.P. Lever, J. Organomet. Chem. 635, 187 (2001), doi: 10.1016/S0022-328X(01)01079-8
• [19] K. Wolinski, J.F. Hinton, P. Pulay, J. Am. Chem. Soc. 112, 8251 (1990), doi: 10.1021/ja00179a005
• [20] W.P. Oziminski, J.C. Dobrowolski, J. Phys. Org. Chem. 22, 769 (2009), doi: 10.1002/poc.1530
• [21] J.P. Merrick, D. Moran, L. Radom, J. Phys. Chem. A 111, 11683 (2007), doi: 10.1021/jp073974n
• [22] T. Arora, H. Ali, W.A. Burns, E. Koizumi, H. Koizumi, Chem. Phys. Lett. 502, 253 (2011), doi: 10.1016/j.cplett.2010.12.035
• [23] M. Silverstein, G.C. Basseler, C. Morill, Spectrometric Identification of Organic Compounds, Wiley, New York 1981
• [24] G. Keresztury, in: Handbook of Vibrational Spectroscopy, Eds. J.M. Chalmers, P.R. Griffiths, Vol. 1, Wiley, New York 2002
• [25] G. Varsanyi, Assignments of Vibrational Spectra of 700 Benzene Derivatives, Wiley, New York 1974
• [26] C. Sridevi, G. Velraj, Spectrochim. Acta A 107, 334 (2013), doi: 10.1016/j.saa.2013.01.044
• [27] H.O. Kalinowski, S. Berger, S. Braun, Carbon-13 NMR Spectroscopy, Wiley, Chichester 1988
• [28] F.L. Tobiason, J.H. Goldstein, Spectrochim. Acta A 23, 1385 (1967), doi: 10.1016/0584-8539(67)80360-X
• [29] K. Fukui, Science 218, 747 (1982), doi: 10.1126/science.218.4574.747
• [30] D. Avcı, Y. Atalay, Struct. Chem. 20, 185 (2009), doi: 10.1007/s11224-008-9400-1
• [31] M. Dinçer, D. Avcı, M. Şekerci, Y. Atalay, J. Mol. Mod. 14, 823 (2008), doi: 10.1007/s00894-008-0324-x
• [32] D. Avcı, Spectrochim. Acta A 82, 37 (2011), doi: 10.1016/j.saa.2011.06.037
• [33] F. Weinhold, C. Landis, Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge University Press, Cambridge 2005
• [34] A.E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88, 899 (1988), doi: 10.1021/cr00088a005
• [35] H. Ratajczak, S. Debrus, M. May, J. Barycki, J. Baran, Bull. Polish Acad. Sci. 48, 189 (2000)
• [36] J.L. Quadar, R. Hierle, J. Appl. Phys. 48, 2699 (1977), doi: 10.1063/1.324120
• [37] P. Kaatz, E.A. Donley, D.P. Shelton, J. Chem. Phys. 108, 849 (1998), doi: 10.1063/1.475448
• [38] L.T. Cheng, W. Tam, S.H. Stevenson, G.R. Meredith, G. Rikken, S.R. Marder, J. Phys. Chem. 95, 10631 (1991), doi: 10.1021/j100179a026
• [39] R.S. Mulliken, J. Chem. Phys. 23, 1833 (1955), doi: 10.1063/1.1740588
• [40] V. Mukherjee, N.P. Singh, R.A. Yadav, Spectrochim. Acta A 73, 249 (2009), doi: 10.1016/j.saa.2009.02.014

Identifiers

DOI

10.12693/APhysPolA.126.679