The structural properties and vibrational frequencies of 2-phenyl-2-imidazoline have been investigated using theoretical and techniques by which a good correlation was observed. The assignments of the vibrational modes were performed with the help of normal co-ordinate analysis following the Scaled Quantum Mechanical Force Field methodology. Natural bond orbital analysis and the highest occupied molecular orbital-lowest unoccupied molecular orbital gap analysis have been carried out. UV-visible spectrum of the compound was recorded and compared with the theoretical UV-visible spectrum of the title molecule using Symmetry Adapted Cluster-Configuration Interaction method which yielded good agreement. Our results reflect that the title compound can be used as good source of UV light.
References
[1]
Vizi, E.S. (1986) Medicinal Research Reviews, 6, 431-449. https://doi.org/10.1002/med.2610060403
[2]
Le Bihan, G., Rondu, F., Pele-Tounian, A., Wang, X., Lidy, S., Touboul, E., Lamouri, A., Dive, G., Huet, J., Pfeiffer, B., Renard, P., Guardiola-Lemaitre, B., Manechez, D., Penicaud, L., Ktorza, A. and Godfroid, J.-J. (1999) Journal of Medicinal Chemistry, 42, 1587-1603. https://doi.org/10.1021/jm981099b
[3]
Li, H.Y., Drummond, S., De Lucca, I. and Boswell, G.A. (1996) Tetrahedron, 52, 11153-11162. https://doi.org/10.1016/0040-4020(96)00578-9
[4]
Ueno, M., Imaizumi, K., Sugita, T., Takata, I. and Takeshita, M. (1995) International Journal of Immunopharmacology, 17, 597-603. https://doi.org/10.1016/0192-0561(95)00057-9
[5]
Schorderet, M. (1992) Pharmacologie: Des Concepts Fondamentaux aux Applications the Rapeutiques. Frison-Roche, Paris, 130-153.
[6]
Rodríguez-Valdez, L.M., Villamisar, W., Casales, M., González-Rodriguez, J.G., Martínez-Villafañe, A., Martinez, L. and Glossman-mitnik, D. (2006) Corrosion Science, 48, 4053-4064. https://doi.org/10.1016/j.corsci.2006.05.036
[7]
González-Rodríguez, C.A., Rodríguez-Gómez, F.J. and Genescá-Llongueras, J. (2008) Electrochimica Acta, 54, 86-90. https://doi.org/10.1016/j.electacta.2008.02.119
[8]
Contreras, C.D., Montejo, M., Lopez Gonzalez, J.J., Zinczuk, J. and Brandan, S.A. (2011) Journal of Raman Spectroscopy, 42, 108-116.
[9]
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J. and Fox, D.J. (2009) Gaussian. Wallingford.
[10]
Dennington, R., Keith, T. and Millam, J. (2009) Gauss View. Version 5, Semichem Inc., Shawnee Mission.
[11]
Rauhut, G. and Pulay, P. (1995) The Journal of Physical Chemistry, 99, 3093-3100. https://doi.org/10.1021/j100010a019
[12]
Pulay, P., et al. (1983) Journal of the American Chemical Society, 105, 7037-7047. https://doi.org/10.1021/ja00362a005
[13]
Fogarasi, G., Pulay, P. and Durig, J.R. (1985) Chapter 3, Vibrational Spectra and Structure. Elsevier, Amsterdam, Vol. 14, 125.
[14]
Sundius, T. (1990) Journal of Molecular Structure, 218, 321-326. https://doi.org/10.1016/0022-2860(90)80287-T
[15]
Sundius, T. (2002) Vibrational Spectroscopy, 29, 89-95. https://doi.org/10.1016/S0924-2031(01)00189-8
[16]
Glendering, E.D., Reed, A.E., Carpenter, J.E. and Weinhold, F. (1998) NBO Version 3.1. TCI, University of Wisconsin, Madison.
[17]
Polavarapu, P.L. (1990) The Journal of Physical Chemistry, 94, 8106-8112. https://doi.org/10.1021/j100384a024
[18]
Keresztury, G., Holly, S., Varga, J., Besenyei, G., Wang, A.Y. and Durig, J.R. (1993) Spectrochimica Acta Part A, 49, 2007-2017. https://doi.org/10.1016/S0584-8539(09)91012-1
[19]
Becke, A.D. (1993) The Journal of Chemical Physics, 98, 5648-5652. https://doi.org/10.1063/1.464913
[20]
Jing, L.-L., Ma, H.-P., He, L., Fan, P.-C. and Jia, Z.-P. (2011) Acta Crystallographica Section E, 67, o3503.
[21]
Pulay, P., Fogarasi, G., Pang, F. and Boggs, J.E. (1979) Journal of the American Chemical Society, 101, 2550.
[22]
Fogarasi, G., Zhou, X., Taylor, P.W. and Pulay, P. (1992) Journal of the American Chemical Society, 114, 8191-8201. https://doi.org/10.1021/ja00047a032
Silverstein, R.M., Basseler, G.C. and Morill, C. (1981) Spectrometric Identification of Organic Compounds. John Wiley and Sons, New York.
[25]
Veeraiah, A. (2015) Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 147, 212-224. https://doi.org/10.1016/j.saa.2015.03.053
[26]
Chandra, S., Saleem, H., Sebastian, S. and Sundaraganesan, N. (2011) Spectrochimica Acta Part A, 78, 1515-1524. https://doi.org/10.1016/j.saa.2011.01.043
[27]
Furic, K., Mohack, V., Bonifacic, M. and Stefanic, I. (1992) Journal of Molecular Structure, 267, 39-44. https://doi.org/10.1016/0022-2860(92)87006-H
[28]
Colthup, N.B., Daly, L.H. and Wiberley, S.E. (1990) Introduction to Infrared and Raman Spectroscopy. Academic Press, New York.
Socrates, G. (2001) Infrared and Raman Characteristic Group Frequencies—Tables and Charts. 3rd Edition, Wiley & Sons, Chichester.
[31]
Nagabalasubramanian, P.B., Periandy, S., Mohan, S. and Govindarajan, M. (2009) Spectrochimica Acta Part A, 73, 277-280. https://doi.org/10.1016/j.saa.2009.02.044
[32]
Silverstein, M., Clayton Bassler, G. and Morril, C. (1981) Spectroscopic Identification of Organic Compounds. John Wiley, New York.
[33]
James, C., AmalRaj, A., Reghunathan, R., Hubert Joe, I. and JayaKumar, V.S. (2006) Journal of Raman Spectroscopy, 37, 1381-1392. https://doi.org/10.1002/jrs.1554
[34]
Na, L.J., Rang, C.Z. and Fang, Y.S. (2005) Journal of Zhejiang University Science B, 6, 584-589.
[35]
Gunasekaran, S., Balaji, R.A., Kumaresan, S., Anand, G. and Srinivasan, S. (2008) Canadian Journal of Analytical Sciences and Spectroscopy, 53, 149-162.
[36]
Murray, J.S. and Sen, K. (1996) Molecular Electrostatic Potentials, Concepts and Applications. Elsevier, Amsterdam.
[37]
Alkorta, I. and Perez, J.J. (1996) International Journal of Quantum Chemistry, 57, 123-135. https://doi.org/10.1002/(SICI)1097-461X(1996)57:1<123::AID-QUA14>3.0.CO;2-9
[38]
Lowdin, P. (1978) Advances in Quantum Chemistry. Academic Press, New York.
[39]
Luque, F.J., Orozco, M., Bhadane, P.K. and Gadre, S.R. (1993) The Journal of Physical Chemistry, 97, 9380-9384. https://doi.org/10.1021/j100139a021
[40]
Sponer, J. and Hobza, P. (1996) International Journal of Quantum Chemistry, 57, 959-970. https://doi.org/10.1002/(SICI)1097-461X(1996)57:5<959::AID-QUA16>3.0.CO;2-S
[41]
Anbarasana, P.M., Subramanian, M.K., Senthilkumar, P., Mohanasundaram, C., Ilangovan, V. and Sundaraganesan, N. (2011) Journal of Chemical and Pharmaceutical Research, 3, 597-612.
[42]
Murray, J.S. and Sen, K. (1996) Molecular Electrostatic Potentials, Concepts and Applications. Elsevier, Amsterdam.
[43]
Scrocco, E. and Tomasi, J. (1978) Electronic Molecular Structure, Reactivity and Intermolecular Forces: An Heuristic Interpretation by Means of Electrostatic Molecular Potentials. In: Lowdin, P.O., Ed., Advances in Quantum Chemistry, Academic Press, New York, p. 115.
[44]
Ignatov, S.K. (2004) Program for Molecular Visualization and Thermodynamic Calculations. University of Nizhny Novgorod, Nizhnij Novgorod. http://ichem.unn.ru/Moltran
