Synthesis, Characterization, and Structural Assessment of Ni(II) Complexes Derived from Bis(2-hydroxy-1-naphthaldehyde)succinoyldihydrazone
This article is part of Special Issue:
Mithun Chakrabarty,
Aziz Ahmed,
R. A. Lal,
Corresponding Author
Mithun Chakrabarty
Department of Chemistry, University of Technology and Management, Shillong, Meghalaya 793003, India
Search for more papers by this authorAziz Ahmed
Department of Chemistry, Indian Institute of Technology Patna, Bihar 801103, India iitp.ac.in
Search for more papers by this authorR. A. Lal
Department of Chemistry, North-Eastern Hill University, Shillong, Meghalaya 793022, India nehu.ac.in
Search for more papers by this authorMithun Chakrabarty,
Aziz Ahmed,
R. A. Lal,
Corresponding Author
Mithun Chakrabarty
Department of Chemistry, University of Technology and Management, Shillong, Meghalaya 793003, India
Search for more papers by this authorAziz Ahmed
Department of Chemistry, Indian Institute of Technology Patna, Bihar 801103, India iitp.ac.in
Search for more papers by this authorR. A. Lal
Department of Chemistry, North-Eastern Hill University, Shillong, Meghalaya 793022, India nehu.ac.in
Search for more papers by this authorAcademic Editor: Alfonso Castiñeiras
Abstract
The monometallic nickel(II) complexes [Ni(H2nsh)(A)2]·nH2O (where A = water (H2O), n = 0 (1); pyridine (py), n = 2 (2); 2-picoline(2-pic), n = 0 (3); 3-picoline(3-pic), n = 2 (4); and 4-picoline(4-pic), n = 0 (5)) and homobimetallic nickel(II) complexes [Ni2(nsh)(A)4]·nH2O (where A = water (H2O), n = 1 (6); pyridine (py), n = 4 (7); 2-picoline(2-pic), n = 4 (8); 3-picoline(3-pic), n = 4 (9); and 4-picoline(4-pic), n = 4 (10), resp.) have been synthesized in methanol from bis(2-hydroxy-1-naphthaldehyde)succinoyldihydrazone (H4nsh). The complexes have been characterized by elemental analyses, molar conductance, magnetic moment, and electronic and IR and TGA/DTA spectroscopic studies. The monometallic complexes (1) to (5) are found to have octahedral stereochemistry while complexes (6) to (10) are found to have distorted octahedral stereochemistry in which one of the Ni(II) centres is present in N2O2 coordination sphere and another Ni(II) centre is bonded to it through phenolate oxygen atoms via oxo-bridging.
Supporting Information
Fig.S1: Infrared spectrum of bis(2-hydroxy-1-naphthaldehyde)succinoyldihydrazone (H4nsh) in KBr.
Fig.S2: Infrared spectrum of [Ni(H2nsh)(py)2]. H2O (2) in KBr.
Fig.S3: Infrared spectrum of [Ni(H2nsh)(2-pic)2] (3) in KBr.
Fig.S4: Infrared spectrum of [Ni2(nsh)(H2O)4] (6) in KBr.
Fig.S5: Infrared spectrum of [Ni2(nsh)(py)4].4H2O (7) in KBr.
Fig.S6: Infrared spectrum of [Ni2(nsh)(4-pic)4].4H2O(10) in KBr.
Fig.7: TGA/DTA curve of complex [Ni(H2nsh)(H2O)2] (1).
Fig.8: TGA/DTA curve of complex [Ni2(H2nsh)(H2O)4].H2O (6).
Fig.9: TGA/DTA curve of complex [Ni2(nsh)(py)4].4H2O (7).
Fig.10: TGA/DTA curve of complex [Ni2(nsh)(2-pic)4].4H2O (8).
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References
- 1 Lal R. A., Chakrabarty M., Choudhury S., Ahmed A., Borthakur R., and Kumar A., Synthesis and spectral characterization of homobimetallic molybdenum(VI) complexes derived from bis(2-hydroxy-1-naphthaldehyde)succinoyldihydrazone, Journal of Coordination Chemistry. (2010) 63, no. 1, 163–175, https://doi.org/10.1080/00958970903259451, 2-s2.0-70450054831.
- 2 Lal R. A., Chakraborty M., Chanu O. B., Choudhury S., Borthakur R., Copperfield S., and Kumar A., Synthesis and characterization of heterobimetallic Ni(II)-Zn(II) complexes from bis(2-hydroxy-1 -naphthaldehyde)succinoyldihydrazone, Journal of Coordination Chemistry. (2010) 63, no. 7, 1239–1251, https://doi.org/10.1080/00958971003759077, 2-s2.0-77951702077.
- 3 Angelici R. J., Heterogeneous catalysis of the hydrodesulfurization of thiophenes in petroleum: an organometallic perspective of the mechanism, Accounts of Chemical Research. (1988) 21, no. 11, 387–394, https://doi.org/10.1021/ar00155a001, 2-s2.0-33845278010.
- 4 Belle C., Bougault C., Averbuch M.-T., Durif A., Pierre J.-L., Latour J.-M., and Le Pape L., Paramagnetic NMR investigations of high-spin nickel(II) complexes. Controlled synthesis, structural, electronic, and magnetic properties of dinuclear vs mononuclear species, Journal of the American Chemical Society. (2001) 123, no. 33, 8053–8066, https://doi.org/10.1021/ja010342k, 2-s2.0-0034821083.
- 5 Meyer F. and Pritzkow H., A bridging coordination mode of urea and carbamate at a dinuclear nickel(II) centre, Chemical Communications. (1998) no. 15, 1555–1556, 2-s2.0-0001673864.
- 6 Andrews R. K., Blakely R. L., and Zerner B., G. L. Eichhorn and L. G. Marzilli, Urea and urease, Advances in Inorganic Biochemistry, 1984, 5, Elsevier, New York, NY, USA, 245–283.
- 7 Mandal S., Bose R. N., Reed J. W., and Gould E. S., Electron transfer. 129. Copper Catalysis in the thiol reduction of oxime-bound nickel(IV), Inorganic Chemistry. (1996) 35, no. 11, 3159–3162, https://doi.org/10.1021/ic951520b, 2-s2.0-0347165213.
- 8 Comprehensive Coordination Chemistry II, 2004, 6, Elsevier, Pergamon, Turkey.
- 9 Fujita E., Brunschwig B. S., Ogata T., and Yanagida S., Toward photochemical carbon dioxide activation by transition metal complexes, Coordination Chemistry Reviews. (1994) 132, 195–200, https://doi.org/10.1016/0010-8545(94)80040-5, 2-s2.0-13344277267.
- 10 Kimura E., Wada S., Shiongya M., and Okazaki Y., New series of multifunctionalized nickel(II)-cyclam (cyclam = 1,4,8,11-tetraazacyclotetradecane) complexes. Application to the photoreduction of carbon dioxide, Inorganic Chemistry. (1994) 33, 770–778.
- 11
Pal S. and
Pal S., Ruthenium(II) complexes containing RuN4O2 spheres assembled via pyridine-imine-amide coordination. Syntheses, structures, properties and protonation behaviour of coordinated amide, Journal of the Chemical Society, Dalton Transactions. (2002) no. 9, 2102–2108, 2-s2.0-0036013750.
10.1039/b110912j Google Scholar
- 12
Dinda R.,
Sengupta P.,
Ghosh S.,
Mayer-Figge H., and
Sheldrick W. S., A family of mononuclear molybdenum-(VI), and -(IV) oxo complexes with a tridentate (ONO) ligand, Journal of the Chemical Society, Dalton Transactions. (2002) no. 23, 4434–4439, https://doi.org/10.1039/B207129K.
10.1039/b207129k Google Scholar
- 13 Al-Hazmi G. A. and El-Asmy A. A., Synthesis, spectroscopy and thermal analysis of copper(II) hydrazone complexes, Journal of Coordination Chemistry. (2009) 62, no. 2, 337–345, https://doi.org/10.1080/00958970802226411, 2-s2.0-57749106482.
- 14 Dinda R., Sengupta P., Ghosh S., and Sheldrick W. S., Synthesis, structure, and reactivity of a new mononuclear molybdenum(VI) complex resembling the active center of molybdenum oxotransferases, European Journal of Inorganic Chemistry. (2003) 2003, no. 2, 363–369, 2-s2.0-0037266454.
- 15 Singh M. K., Kar N. K., and Lal R. A., Synthesis and characterization of manganese(IV) and ruthenium(III) complexes derived from bis(2-hydroxy-1-naphthaldehyde)oxalyl dihydrazone, Journal of Coordination Chemistry. (2008) 61, no. 19, 3158–3171.
- 16 Lal R. A., Basumatary D., Adhikari S., and Kumar A., Synthesis and properties of mononuclear and binuclear molybdenum complexes derived from bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazone, Spectrochimica Acta—Part A: Molecular and Biomolecular Spectroscopy. (2008) 69, no. 3, 706–714, https://doi.org/10.1016/j.saa.2007.05.023, 2-s2.0-43049117542.
- 17 Zhao L., Niel V., Thompson L. K., Xu Z., Milway V. A., Harvey R. G., Miller D. O., Wilson C., Leech M., Howard J. A. K., and Heath S. L., Self-assembled polynuclear clusters derived from some flexible polydentate dihydrazide ligands, Dalton Transactions. (2004) no. 9, 1446–1455, 2-s2.0-2642563746.
- 18 Carcelli M., Ianelli S., Pelagatti P., Pelizzi G., Rogolino D., Solinas C., and Tegoni M., Synthesis and characterization of new lanthanide complexes with hexadentate hydrazonic ligands, Inorganica Chimica Acta. (2005) 358, no. 4, 903–911, https://doi.org/10.1016/j.ica.2004.10.003, 2-s2.0-13844313398.
- 19 Naskar S., Mishra A D., and Chattopadhyay S. K., Synthesis, characterization, and crystal structure of [Ni(dap(A)2)]2 (dap(AH)2: 2,6-diacetylpyridine bis(anthraniloyl hydrazone))—a molecule possessing an infinite double helical chain in the solid state, Structural Chemistry. (2007) 18, no. 2, 217–222, https://doi.org/10.1007/s11224-006-9086-1.
- 20 Ranford J. D., Vittal J. J., and Wang Y. M., Dicopper(II) complexes of the antitumor analogues acylbis(salicylaldehyde hydrazones) and crystal structures of monomeric [Cu2(1,3-propanedioyl bis(salicylaldehyde hydrazone))(H2O)2]·(ClO4)2·3H2O and polymeric [{Cu2(1,6-hexanedioyl bis(salicylaldehyde hydrazone))(C2H5OH)2}m]·(ClO4)2m·m(C2H5OH), Inorganic Chemistry. (1998) 37, no. 6, 1226–1231, https://doi.org/10.1021/ic970805g.
- 21 Aggarwal R. C. and Narang K. K., N-acetyl, N′-benzoyl hydrazine complexes of cobalt(II), nickel(II) and copper(II), Inorganica Chimica Acta. (1973) 7, 651–652, https://doi.org/10.1016/s0020-1693(00)94903-x.
- 22 Lal R. A., Siva A. N., Adhikari S., Singh M. K., and Yadav U. S., Synthesis and spectral characterization of dioxouranium(VI) complexes of disalicylaldehyde adipoyldihydrazone, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. (1996) 26, no. 2, 321–337, https://doi.org/10.1080/00945719608004267, 2-s2.0-0030556005.
- 23 Feigl F., Anger V., and Oesper R. E., Spot Tests in Organic Analysis, 1966, 7th edition, Elsevier, Amsterdam, The Netherlands, Indian Reprint 2005.
- 24 Lal R. A., Adhikari S., Pal A., Siva A. N., and Kumar A., Synthesis and characterization of the homobimetallic [bis(2-hydroxy-1-naphthaldehyde)oxaloyldihydrazonato]bis(dioxomolybdenum(VI)) tetrahydrate complex and its reactivity towards proton and electron donor reagents, Journal of Chemical Research—Part S. (1997) no. 4, 122–123, https://doi.org/10.1039/A506810J, 2-s2.0-2542609325.
- 25 Geary W. J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews. (1971) 7, no. 1, 81–122, https://doi.org/10.1016/S0010-8545(00)80009-0, 2-s2.0-0001813985.
- 26 Ismail T. M. A., Mononuclear and binuclear Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes of Schiff-base ligands derived from 7-formyl-8-hydroxyquinoline and diaminonaphthalenes, Journal of Coordination Chemistry. (2005) 58, no. 2, 141–151, https://doi.org/10.1080/0095897042000274733, 2-s2.0-27844470295.
- 27 Shakir M., Azim Y., Chishti H. T. N., Begum N., Chingsubam P., and Siddiqi M. Y., Synthesis, physico-chemical and antimicrobial screening studies on 14 and 16-membered hexaazamacrocyclic complexes bearing pendant amine groups, Journal of the Brazilian Chemical Society. (2006) 17, no. 2, 272–278, https://doi.org/10.1590/s0103-50532006000200009, 2-s2.0-33645317061.
- 28 Nyburg S. C. and Wood J. S., The molecular structures of Lifschitz nickel(II) complexes. II. The crystal structures of one of the blue and of one of the yellow forms of bis(meso-stilbenediamine)nickel(II) dichloroacetate, Inorganic Chemistry. (1964) 3, no. 4, 468–476, https://doi.org/10.1021/ic50014a002, 2-s2.0-26544465802.
- 29 Savant V. V., Gopalakrishnan J., and Patel C. C., Metal monothiobenzoates, Inorganic Chemistry. (1970) 9, no. 4, 748–751, https://doi.org/10.1021/ic50086a011.
- 30 Nigam H. L. and Pandeya K. B., On mixed stereochemistry of a binuclear nickel-thiovanol complex, Current Science. (1972) 41, no. 12, 449–451.
- 31 Levason W. and McAuliffa C. A., Bidentate group VB chelates. Part XV. Four- and five-coordinate cobalt(II) complexes of very soft donors. Planar coordination, Inorganica Chimica Acta. (1975) 14, 127–132, https://doi.org/10.1016/S0020-1693(00)85732-1.
- 32 Dutta R. L. and Hossain M., Coordination chemistry of acyl, aroyl, heteroaroyl hydrazones and related ligands, Journal of Scientific and Industrial Research. (1985) 44, no. 12, 635–674, 2-s2.0-0022246006.
- 33 Mohan M., Gupta N. K., Kumar M., Jha N. K., and Antholine W. E., Synthesis, magnetic and electrochemical properties of binuclear copper(II) complexes of pyridoxal hydrazones, Inorganica Chimica Acta. (1992) 197, no. 1, 39–46, https://doi.org/10.1016/S0020-1693(00)85517-6, 2-s2.0-4243361843.
- 34 Chan S. C., Koh L. L., Leung P.-H., Ranford J. D., and Sim K. Y., Copper(II) complexes of the antitumour-related ligand salicylaldehyde acetylhydrazone (H2L) and the single-crystal X-ray structures of [{Cu(HL)H2O}2] · 2(NO3) and [{Cu(HL) (pyridine) (NO3)}2], Inorganica Chimica Acta. (1995) 236, no. 1-2, 101–108, https://doi.org/10.1016/0020-1693(95)04623-h.
- 35 Sorrell T. N., Synthetic models for binuclear copper proteins, Tetrahedron. (1989) 45, no. 1, 3–68, https://doi.org/10.1016/0040-4020(89)80033-X, 2-s2.0-0039524832.
- 36 Shijo Y., Shimizu T., and Sakai K., Extractive spectrophotometric determination of antimony(III), bismuth, indium, and gallium with pyrocatechol violet and tridodecylethylammonium bromide, Bulletin of the Chemical Society of Japan. (1983) 56, no. 1, 105–107, https://doi.org/10.1246/bcsj.56.105.
- 37 Al-Awadi N., Shuaib N. M., and El-Dissouky A., Synthesis and spectroscopic characterization of nickel(II) complexes of 1-benzotriazol-1-yl-[(p-X-phenyl)hydrazone]propan-2-one, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. (2006) 65, no. 1, 36–43, https://doi.org/10.1016/j.saa.2005.09.024, 2-s2.0-33746673133.
- 38 Lever A. B. P., Electronic spectra of some transition metal complexes: derivation of Dq and B, Journal of Chemical Education. (1968) 45, no. 11, 711–712, https://doi.org/10.1021/ed045p711, 2-s2.0-18944380029.
- 39 Adhikary B., Liu S., and Lucas C. R., Comparative studies of mononuclear nickel(II) complexes with N2Sx(x = 2 − 4) ligands, Inorganic Chemistry. (1993) 32, no. 26, 5957–5962, https://doi.org/10.1021/ic00078a011, 2-s2.0-0000474289.
- 40 Lever A. B. P., The electronic spectra of tetragonal metal complexes analysis and significance, Coordination Chemistry Reviews. (1968) 3, no. 2, 119–140, https://doi.org/10.1016/S0010-8545(00)80107-1, 2-s2.0-0001831589.
- 41 Abd El-Wahab Z. H., Mononuclear metal complexes of organic carboxylic acid derivatives: synthesis, spectroscopic characterization, thermal investigation and antimicrobial activity, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. (2007) 67, no. 1, 25–38, https://doi.org/10.1016/j.saa.2006.05.038, 2-s2.0-33947668389.
- 42 Radhakrishnan P. K., Indrasenan P., and Nair C. G. R., Complexes of lanthanide nitrates with 4n-(2′-hydroxy benzylidene)-aminoantipyrine, Polyhedron. (1984) 3, no. 1, 67–70, https://doi.org/10.1016/s0277-5387(00)84714-2, 2-s2.0-0004546006.
- 43 Agarwal R. K. and Prakash J., Synthesis and characterization of thorium(IV) and dioxouranium(VI) complexes of pentamethylene sulphoxide, Polyhedron. (1991) 10, no. 22, 2567–2571, https://doi.org/10.1016/S0277-5387(00)81331-5, 2-s2.0-0013525222.
- 44 Mohamed G. G. and Sharaby C. M., Metal complexes of Schiff base derived from sulphametrole and o-vanilin. Synthesis, spectral, thermal characterization and biological activity, Spectrochimica Acta—Part A: Molecular and Biomolecular Spectroscopy. (2007) 66, no. 4-5, 949–958, https://doi.org/10.1016/j.saa.2006.04.033, 2-s2.0-33847327319.
- 45 Gup R. and Kirkan B., Synthesis and spectroscopic studies of copper(II) and nickel(II) complexes containing hydrazonic ligands and heterocyclic coligand, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. (2005) 62, no. 4-5, 1188–1195, https://doi.org/10.1016/j.saa.2005.04.015, 2-s2.0-27844567737.
- 46
Griffith W. P.,
Pumphrey C. A., and
Rainey T.-A., Catecholato complexes of ruthenium, iridium, rhenium, molybdenum, and tungsten, Journal of the Chemical Society, Dalton Transactions. (1986) 1125–1128, https://doi.org/10.1039/dt9860001125, 2-s2.0-37049074076.
10.1039/dt9860001125 Google Scholar
- 47
El-Hendawy A. M.,
Griffith W. P., and
Pumphrey C. A., Complexes of osmium, uranium, molybdenum, and tungsten with the catechol amines adrenaline, noradrenaline, dopamine, dopa, and isoproterenol, Journal of the Chemical Society, Dalton Transactions. (1988) no. 7, 1817–1821, https://doi.org/10.1039/DT9880001817, 2-s2.0-34548727911.
10.1039/dt9880001817 Google Scholar
- 48 Lal R. A., Pal M. L., and Adhikari S., Synthesis, characterization and some properties of oxoperoxo complexes of molybdenum with 2-hydroxy-1-naphthaldehyde isonicotinoylhydrazone, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. (1996) 26, no. 6, 997–1023, https://doi.org/10.1080/00945719608004348, 2-s2.0-0030534880.
- 49 Sartori G., Furlani C., and Damiani A., On the problem of the vibrational frequencies of water in complexes, Journal of Inorganic and Nuclear Chemistry. (1958) 8, 119–125, https://doi.org/10.1016/0022-1902(58)80172-4.
