Mehmet AKKURT, Muhammad Nawaz TAHİR, Ahmet Oral SARIOĞLU, Tuğba TAŞKIN TOK, Mehmet SÖNMEZ

Synthesis and structural properties ofN-3,4-(dichlorophenyl)-3-oxo-3-phenyl-2-(phenylcarbonyl)propanamide and its Cu(II) complex

A new N-carboxamide compound (3) was synthesized by the reaction of dibenzoylaceticacid-N-carboxyethyla-mide (1) and 3,4-dichloroaniline (2). TheN-(3,4-dichlorophenyl)-3-oxo-3-phenyl-2-(phenylcarbonyl) propanamide (3)subsequently reacted with Cu salt to produce its Cu(II) complex compound (4). The compounds were characterized byanalytical and spectral methods. In addition, X-ray diffraction was performed to characterize and obtain detailed infor-mation about the structure of3. The fully optimized geometries of compounds3and4were calculated at different basissets by using the Gaussian09 (G09) software to investigate their 3D geometries and electronic structures. Comparisonsbetween the calculated and experimental data including molecular structures, fundamental vibrational modes, and elec-tronic properties were made. The comparisons showed that the theoretical data were compatible with the correspondingexperimental values of compounds3and4.

PDF

___

1.Hranjec, M.; Sovic, I.; Ratkaj, I.; Pavlovic, G.; Ilic, N.; Valjalo, L.; Pavelic, K.; Pavelic, S. K.; Zamola, G. K.Eur.J. Med. Chem.2013,59, 111-119.
2.Strupi, M.; Roata , G.; Stables, J. P.; Pruszewski, R.Acta Pol. Pharm.2009,66, 155-159.
3.Sonmez, M.Turk. J. Chem.2001,25, 181-185.
4.Panda, C.; Ghosh, M.; Panda, T.; Banerjee, R.; Gupta, S .S.Chem. Commun.2011,47, 8016-8018.
5.Singh, A. K.; Balamurugan, V.; Mukherjee, R.Inorg. Chem.2003,42, 6497-6502.
6.Noveron,J. C.; Olmstead, M. M.; Mascharak, P. K.Inorg. Chem.1998,37, 1138-1139.
7.Raymond, K. N.; Carrano, C. J.Acc. Chem. Res.1979,12, 183-190.
8.Bhowan, M. G.; Lanlloo, S. J.; Ramnial, T.Trans. Met. Chem.2001,26, 329-332.
9.Millhauser, G. L.Acc. Chem. Res.2004,37, 79-85.
10.Fabian, W. F.; Kollenz, G.; Akcamur, Y.; Kok, T. R.; Tezcan, M.; Akkurt, M.; Hiller, W.Monath. Chem.1992,123, 265-275.
11.Bhaskare, C.; Hankare, P. P.;J. Indian Chem. Soc.1995,72, 585-587.
12.Nishat, N.; Rahis ud-din, Haq, M. M.;Pol. J. Chem.2003,77, 1731{ 1740.
13.Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R.J. Chem Soc. Perkin Trans II:1987,S1-19.
14.Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang N. L.Angew Chem Int Ed Engl1995,34, 1555{1573.
15.Mulliken, R. S.J. Chem. Phys.1955,23, 1833{1840.
16.Becke, A. D.J.Chem. Phys.1993,98, 5648-5652.
17.Lee, C.; Yang, W.; Parr, R. G.Phys. Rev. B.1988,37, 785-789.
18.Hohenberg, P.; Kohn, W.Phys. Rev. B.1964,136, 864-871.
19.Foresman, J. B. in: E. Frisch (Ed.), ExploringChemistry with Electronic Structure Methods:A Guide to UsingGaussian, Gaussian, Inc., Pittsburg, PA,1996.
20.Murray, J. S.; Sen, K.Molecular Electrostatic Potentials, Concepts and Applications,Elsevier, Amsterdam,1996.
21.Alcorta, I.; Perez, J. J.Int. J. Quant. Chem.1996,57, 123-135.
22.Scrocco, E.; Tomasi, J.Advances in Quantum Chemistry, ed. P. Lowdin, Academic Press, New York,1978,115-143.
23.Luque, F. J.; Orozco, M.; Bhadane, P. K.; Gadre, S. R.J. Phys. Chem.1993,97, 9380-9384.
24.Sponer, J.; Hobza, P.Int. J. Quant. Chem.1996,57, 959-970.25.Pathak, R. K.; Gadre, S. R.J. Chem. Phys.1990,93, 1770-1773.
26.Gadre, S. R.; Shrivastava, I. H.J. Chem. Phys.1991,94, 4384-4390.
27.Scrocco, E.; Tomasi, J.Adv. Quantum. Chem.1978,11, 115{193.
28.Luque, F. J.; Lopez, J. M.; Orozco, M.Theor. Chem. Acc.2000,103, 343{345.
29.Fleming, I.Frontier Orbitals and Organic Chemical Reactions,John Wiley and Sons, New York,1976.
30.Parr, R. G.; Szentpaly, L. V.; Liu, S.J. Am. Chem. Soc.1999,121, 1922-1924.
31.Maynard, A. T.; Huang, M.; Rice, W. G.; Covell, D. G.Proc. Natl. Acad. Sci. USA,1998,95, 11578-11583.
32.Chattaraj, P. K.; Giri, S.; Duley, S.Chem. Rev.2011,111, 43-75.
33.Taskin, T.; Sevin, F.J. of Mol. Struc.: Theochem2007,803, 61{66.
34.Parthasarathi, R.; Subramanian, V.; Royb, D. R.; Chattaraj, P. K.Bioorg. and Med. Chem.2004,12, 5533{5543.
35.Taskin, T.; Sevin, F.Turk. J. Chem.2011,35, 481-498.
36.Sheldrick, G. M.Acta. Cryst.2008,A64, 112{122.
37.Farrugia, L. J.J. Appl .Cryst.1997,30, 565-566.
38.Spek, A. L.Acta Cryst.2009,D65, 148{155.
39.Gaussian 09, Revision C.01, 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.; et. al. Gaussian, Inc., Wallingford CT,2011.
40.Hay, P. J.; Wadt, W. R.J. Chem. Phys.1985,82, 270{283.
41.Zhao, J. Y.; Zhang, Y.; Zhu, L. G.J. Mol. Struct. Theochem.2004,671, 179{187.
42.Stewart, J. J. P.J. Mol. Model.2007, 13, 1173-213.