Synthesis and spectral characterization of naphthyldihydrazones derived from some 1,3- dicarbonyl compounds and their Ni(II), Cu(II) and Zn(II) complexes

Authors

1 Department of Chemistry, KAHM Unity Women’s College, Manjeri, Kerala-676122, India

2 Department of Chemistry, University of Calicut, Kerala-673635, India

Abstract

The coupling of tetrazotised 1,8-diaminonaphthalene with 1,3-dicarbonyl compounds [acetylacetone,
methylacetoacetate and acetoacetanilide] yielded a new series of tetradentate ligand systems. Analytical, IR,
1H NMR and mass spectral data indicate that the compounds exist in the intramolecularly hydrogen bonded
dihydrazone form. Dibasic tetradentate N2O2 coordination of these compounds in their [ML] complexes [M
= Ni(II), Cu(II) and Zn(II)] has been established on the basis of analytical and spectral data. The Ni(II) and
Zn(II) chelates are diamagnetic while Cu(II) complexes showed normal paramagnetic moment.

Keywords


[1] P.F. Gorden, P. Gregory, Organic Chemistry in Colour, Springer-Verlag, New York, 1983.
[2] K. Krishnankutty, M.B. Ummathur, D.K. Babu, P.M. Philip, J. Iran. Chem. Res. 2 (2009) 111-119.
[3] H.C. Yao, J. Org. Chem. 29 (1964) 2959-2963.
M.B. Ummathur et al., J. Iranian Chem. Res. 5 (1) (2012) 23-29
29
[4]M.S. Masoud, G.B. Mohamed, Y.H. Abdul-Razek, A.E. Ali, F.N. Khairy, J. Korean Chem. Soc. 46
(2002) 99-116.
[5] M.I. Toral, P. Richter, N. Lara, M.T. Escudero, C. Soto, Anal. Lett. 33 (2000) 93-109.
[6] J.J. Arias, F. Jiménez, A.I. Jiménez, F.G. Montelongo, Anales de Química 79 (1983) 248-253.
[7] S. Patai, The Chemistry of Diazonium and Diazo Groups, John Wiley, Chichester, 1978.
[8] A. Lycka, D. Lustinee, J. Holecek, M. Nadvornik, M. Holcapek, Dyes and pigments 50 (2001) 203-209.
[9] S.R. Gadzhieva, T.M. Mursalov, K.T. Makmudov, F.M. Chyragov, J. Anal. Chem. 61 (2006) 550-555.
[10] M.B. Ummathur, A. Krishnan, P. Ummer, Inorg. Chem. - An Indian J. 6 (2011) 104-107.
[11] K. Krishnankutty, M.B. Ummathur, P. Ummer, J. Indian Chem. Soc. 87 (2010) 667-672.
[12] K. Krishnankutty, M.B. Ummathur, D.K. Babu, J. Serb. Chem. Soc. 75 (2010) 639-648.
[13] K. Krishnankutty, M.B. Ummathur, P. Ummer, J. Serb. Chem. Soc. 74 (2009) 1273-1282.
[14] K. Krishnankutty, M.B. Ummathur, D.K. Babu, Inorg. Chem. - An Indian J. 4 (2009) 83-87.
[15] M.B. Ummathur, Polish J. Chem. 89 (2009) 1717-1728.
[16] K. Krishnankutty, P. Sayudevi, M.B. Ummathur, J. Indian Chem. Soc. 84 (2007) 518-523.
[17] K. Krishnankutty, P. Sayudevi, M.B. Ummathur, J. Indian Chem. Soc. 84 (2007) 337-340.
[18] K.H. Saunders, R.L.M. Allen, Aromatic Diazo compounds, 3rd Edn., Edward Arnold, London, 1985.
[19] N.H. Al-Shaalan, Molecules 16 (2011) 8629-8645.
[20] E. König, Magnetic Properties of Coordination and Organometallic Transition Metal Compounds,
Springer-Verlag, Berlin, 1966.
[21] L.J. Bellamy, The Infrared spectra of Complex Molecules, Chapman and Hall, London, 1980.
[22] C.N.R. Rao, Chemical Applications of Infrared Spectroscopy, Academic Press, London, 1963.
[23] N. Nakamoto, Infrared Spectra and Raman Spectra of Inorganic and Coordination Compounds, John
Wiley & Sons, New York, 1997.
[24] K. Krishnankutty, J. Michael, J. Coord. Chem. 28 (1993) 259-263.
[25] A. Lycka, J. Jirman, A. Cee, Mag. Reson. Chem. 28 (1990) 408-413.
[26] A.G. Evans, J.C. Evans, B.A. El-Shetary, C.C. Rowlands, P.H. Morgan, J. Cord. Chem. 9 (1979) 19-29.
[27] N. Raman, V. Muthuraj, S. Ravichandran, A. Kulandaisamy, Proc. Indian Acad. Sci. 115 (2003) 161-
167.
[28] H. Budzikiewicz, C. Djerassi, D.H. Williams, Mass spectrometry of organic compounds, Holden Day,
San Francisco, 1967.
[29] K. Kobayashi, K. Kurishara, K. Hirose, Bull. Chem. Soc. Jpn. 45 (1972) 3551-3555.
[30] K. Ray, T. Weyhermüller, F. Neese, K. Wieghardt, Inorg. Chem. 44 (2005) 5345-5360.