Synthesis, spectral characterization and catalytic studies of new ruthenium(II) chalcone thiosemicarbazone complexes

• Autorzy: Manisekar Muthukumar , Periasamy Viswanathamurthi
• Języki publikacji: EN

Abstrakty

EN

A series of new hexa-coordinated ruthenium(II) complexes of the type [Ru(CO)(EPh3)(B)(L)] (E = P or As; B = PPh3, AsPh3 or Py; L = chalcone thiosemicarbazone) have been prepared by reacting [RuHCl(CO)(EPh3)2(B)] (E = P or As; B = PPh3, AsPh3 or Py) with chalcone thiosemicarbazones in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR, UV-vis, 1H, 31P and 13C NMR) methods. On the basis of data obtained, an octahedral structure was assigned for all of the complexes. The chalcone thiosemicarbazones behave as dianionic tridentate O, N, S donors and coordinate to ruthenium via the phenolic oxygen of chalcone, the imine nitrogen of thiosemicarbazone and thienol sulfur. The new complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones and they were also found to be efficient catalysts for the transfer hydrogenation of carbonyl compounds. [...]

Słowa kluczowe

EN

Spectroscopic characterization; Catalytic oxidation; Catalytic transfer hydrogenation; Chalcone thiosemicarbazone complexes

• Czasopismo: Open Chemistry
• Rocznik: 2010
• Tom: 8
• Numer: 1
• Strony: 229-240

Daty

wydano

2010-02-01

online

2010-02-16

Twórcy

autor

Manisekar Muthukumar

• Department of Chemistry, Periyar University, Salem, 636011, India

autor

Periasamy Viswanathamurthi

• Department of Chemistry, Periyar University, Salem, 636011, India,

Bibliografia

• [1] G. Simmons, L.B. Hobson, A. Resnick, R. De Nicola, R.H. Bennett, G. Rake, Trans. Annu. Meet. Natl. Tuberc. Assoc. 46, 124 (1950)
• [2] F. Gialdi, R. Ponci, Farmaco 6, 332 (1951)
• [3] P. Mantegazza, R. Tommasini, Farmaco 6, 264 (1951)
• [4] A. Kolocouris et al., Bioorg. Med. Chem. Lett. 12, 723 (2002) http://dx.doi.org/10.1016/S0960-894X(01)00838-1[Crossref]
• [5] A. De Logu et al., Int. J. Antimicrob. Ag. 26, 28 (2005) http://dx.doi.org/10.1016/j.ijantimicag.2005.03.005[Crossref]
• [6] M.R. Maurya, S.K. Shailendra, A. Azam, W. Zhang, D. Rehder, Eur. J. Inorg. Chem. 24, 3 (2003)
• [7] T. Bal, B. Atasever, Z. Solakoglu, S. Erdem-Kuruca, B. Ulkuseven, Eur. J. Med. Chem. 42, 161 (2007) http://dx.doi.org/10.1016/j.ejmech.2006.09.004[Crossref]
• [8] V. Mishra, S.N. Pandeya, C. Pannecouque, M. Witvrouw, E. De Clercq, Arch. Pharm. 335, 183 (2002) http://dx.doi.org/10.1002/1521-4184(200205)335:5<183::AID-ARDP183>3.0.CO;2-U[Crossref]
• [9] M. Das, S.E. Livingstone, Br. J. Cancer 37, 466 (1978) [Crossref]
• [10] F. Basuli, S.M. Peng, S. Bhattacharya, Inorg. Chem. 39, 1120 (2000) http://dx.doi.org/10.1021/ic991083r[Crossref]
• [11] P. Sengupta, R. Dinda, S. Ghosh, W.S. Sheldrick, Polyhedron 22, 447 (2003) http://dx.doi.org/10.1016/S0277-5387(02)01363-3[Crossref]
• [12] P. Sengupta, R. Dinda, S. Ghosh, A.K. Guha, Trans. Met. Chem. 27, 290 (2002) http://dx.doi.org/10.1023/A:1014824905600[Crossref]
• [13] A. Karam et al., J. Mol. Catal. A. Chem. 265, 127 (2007) http://dx.doi.org/10.1016/j.molcata.2006.09.048[Crossref]
• [14] M. Cai, J. Sha, Catal. Commun. 8, 1691 (2007) http://dx.doi.org/10.1016/j.catcom.2007.01.038[Crossref]
• [15] T.E. Barder, J. Am. Chem. Soc. 128, 898 (2006) http://dx.doi.org/10.1021/ja0558995[Crossref]
• [16] G.B.W.L. Ligthart, R.H. Meijer, M.P. Hulshof, Tetrahedron Lett. 44, 1507 (2003) http://dx.doi.org/10.1016/S0040-4039(02)02842-3[Crossref]
• [17] V. Mahalingam, R. Karvembu, V. Chinnusamy, K. Natarajan, Spectrochim. Acta A 64, 886 (2006) http://dx.doi.org/10.1016/j.saa.2005.08.018[Crossref]
• [18] R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidation of Organic Compounds (Academic Press, New York, 1981)
• [19] C.L. Hill, A.L. Baumstark (Eds.), Advances in Oxygenated Processes (JAI Press Inc, London, 1998) 1
• [20] M. Hudlucky, Oxidations in Organic Chemistry, ACS Monograph Series (American Chemical Society, Washington, DC, 1990)
• [21] A. Madin, B.M. Trost, I. Fleming, S.V. Ley (Eds.), Comprehensive Organic Synthesis (Pergamon Press, Oxford, 1991) 251
• [22] G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 92, 1051 (1992) http://dx.doi.org/10.1021/cr00013a015[Crossref]
• [23] R.A.W. Johnstone, A.H. Wilby, I.D. Entwiste, Chem. Rev. 85, 129 (1985) http://dx.doi.org/10.1021/cr00066a003[Crossref]
• [24] C.F. De Graauw, J.A. Peters, H. Van Bekkum, J. Huskens, Synthesis 10, 1007 (1994) http://dx.doi.org/10.1055/s-1994-25625[Crossref]
• [25] M.J. Palmer, M. Wills, Tetrahedron Asymmetry 10, 2045 (1999) http://dx.doi.org/10.1016/S0957-4166(99)00216-5[Crossref]
• [26] V. Guiral, F. Delbecq, P. Sautet, Organometallics 19, 1589 (2000) http://dx.doi.org/10.1021/om990603n[Crossref]
• [27] Y.R.S. Laxmi, J.E. Backvall, Chem. Commun. 7, 611 (2000) http://dx.doi.org/10.1039/b000530o[Crossref]
• [28] J. Lopez, J.S. Valente, J.M. Clacens, F. Figueras, J. Catal. 208, 30 (2002) http://dx.doi.org/10.1006/jcat.2002.3563[Crossref]
• [29] S.N. Coman, V.I. Parvulescu, M. De Bruyn, D.E. De Vos, P.A. Jacobs, J. Catal. 206, 218 (2002) http://dx.doi.org/10.1006/jcat.2001.3432[Crossref]
• [30] D. Maillard, G. Pozzi, S. Quici, D. Sinou, Tetrahedron 58, 3971 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00247-8[Crossref]
• [31] H.Y. Rhyoo, H.J. Park, W.H. Suh, W.K. Chung, Tetrahedron Lett. 43, 269 (2002) http://dx.doi.org/10.1016/S0040-4039(01)02132-3[Crossref]
• [32] Y. Himeda, N. Onozawa-Komatsuzaki, H. Sugihara, H. Arakawa, K. Kasuga, J. Mol. Catal. A Chem. 195, 95 (2003) http://dx.doi.org/10.1016/S1381-1169(02)00576-9[Crossref]
• [33] C. Bubert et al., Tetrahedron Lett. 42, 4037 (2001) http://dx.doi.org/10.1016/S0040-4039(01)00623-2[Crossref]
• [34] T.J. Geldbach, P.J. Dyson, J. Am. Chem. Soc.126, 8115 (2004) http://dx.doi.org/10.1021/ja048886k[Crossref]
• [35] I. Hannedouche, G.J. Clarkson, J. Am. Chem. Soc. 126, 987 (2004) http://dx.doi.org/10.1021/ja0392768[Crossref]
• [36] W. Baratta, P. Da Ross, A. Del Zotto, A. Sechi, E. Zangrando, P. Rigo, Angew. Chem. Int. Ed. Engl. 43, 3588 (2004) http://dx.doi.org/10.1002/anie.200454199[Crossref]
• [37] S. Burling, M.K. Whittlesey, J.M.J. Williams, Adv. Synth. Catal. 347, 594 (2005) http://dx.doi.org/10.1002/adsc.200404308[Crossref]
• [38] M. Hudlicky, Reductions in Organic Chemistry, American Chemical Society, (Washington, DC, 1996)
• [39] D.J. Darensbourg, F. Joo, M. Kannisto, A. Katho, J.H. Reibenspies, Organometallics 11, 1993 (1992) http://dx.doi.org/10.1021/om00042a007[Crossref]
• [40] S. Naskar, M. Bhattacharjee, J. Organomet. Chem. 690, 5010 (2005) http://dx.doi.org/10.1016/j.jorganchem.2005.08.006[Crossref]
• [41] B.M. Trost, I. Fleming (Eds.), Comprehensive Organometallic Chemistry (Pergamon, Oxford, 1991)
• [42] A.I. Vogel, Textbook of Practical Organic Chemistry, 5th edition (ELBS, London, 1989)
• [43] N. Ahmed, J.J. Lewison, S.D. Robinson, M.F. Uttley, Inorg. Synth. 15, 48 (1974)
• [44] R.A. Sanchez-Pelgado, W.Y. Lee, S.R. Choi, Y. Cho, M.J. Jun, Trans. Met. Chem. 16, 241 (1991) http://dx.doi.org/10.1007/BF01032844[Crossref]
• [45] S. Gopinathan, I.R. Unny, S.S. Deshpande, C. Gopinathan, Ind. J. Chem. A 25, 1015 (1986)
• [46] K. Shanker, R. Rohini, V. Ravinder, P. Muralidhar Reddy, Y.-P. Ho, Spectrochim. Acta A 73, 205 (2009) http://dx.doi.org/10.1016/j.saa.2009.01.021[Crossref]
• [47] R. Prabhakaran et al., J. Inorg. Biochem. 98, 2131 (2004) http://dx.doi.org/10.1016/j.jinorgbio.2004.09.020[Crossref]
• [48] S. Kannan, M. Sivagamasundari, R. Ramesh, Y. Liu, J. Organomet. Chem. 693, 2251 (2008) http://dx.doi.org/10.1016/j.jorganchem.2008.03.023[Crossref]
• [49] K.P. Balasubramanian, R. Karvembu, R. Prabhakaran, V. Chinnusamy, K. Natarajan, Spectrochim. Acta A 68, 50 (2007) http://dx.doi.org/10.1016/j.saa.2006.10.049[Crossref]
• [50] R.K. Sharma, R.V. Singh, J.P. Tandon, J. Inorg. Nucl. Chem. 42, 1382 (1980) http://dx.doi.org/10.1016/0022-1902(80)80313-7[Crossref]
• [51] M.J.M. Cambell, Coord. Chem. Rev. 15, 279 (1975) http://dx.doi.org/10.1016/S0010-8545(00)80276-3[Crossref]
• [52] M. Sivagamasundari, R. Ramesh, Spectrochim. Acta A 67, 256 (2007) http://dx.doi.org/10.1016/j.saa.2006.07.010[Crossref]
• [53] M.V. Kaveri, R. Prabhakaran, R. Karvembu, K. Natarajan, Spectrochim. Acta A 61, 2915 (2005) http://dx.doi.org/10.1016/j.saa.2004.11.001[Crossref]
• [54] W.H. Leung, C.M. Che, Inorg. Chem. 28, 4619 (1989) http://dx.doi.org/10.1021/ic00325a016[Crossref]
• [55] A.M. El-Hendawy, A.H. Alkubaisi, A.E. Kourashy, M.M. Shanab, Polyhedron 12, 2343 (1993) http://dx.doi.org/10.1016/S0277-5387(00)83051-X[Crossref]
• [56] M.M.T. Khan, Ch. Sreelatha, S.A. Mirza, G. Ramachandraiah, S.H.R. Abdi, Inorg. Chim. Acta 154, 103 (1988) http://dx.doi.org/10.1016/S0020-1693(00)85173-7[Crossref]

Identyfikatory

DOI

10.2478/s11532-009-0116-x