Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Spectroscopic, Thermal and Antimicrobial Study of Some Transition Metal(II) Complexes of β-Diketones
Corresponding Author(s) : S. Sharma
Asian Journal of Chemistry,
Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020
Abstract
A novel heterocyclic based β-diketone has been synthesized by the condensation of pyrazole-1-acetylchloride and sodium acetophenone. The product 1-phenyl-4-(pyrazole-1-yl)butane-1,3-dione has been used for complexation with Mn(II), Fe(II) and Co(II) metal ions. The ligand β-diketone is found to exist in keto-enol tautomeric forms. The comparision of infrared spectra of complexes clearly indicates the coordination of the ligand from its enolic form. The magnetic moment and electronic spectra of all the metal complexes leads to the distorted octahedral symmetry around the metal ion. The ligand as well as its metal complexes has been screened for antimicrobial activity and antifungal activities. It is observed that the antimicrobial and antifungal activities get enhanced in complexes in respect to the free ligand.
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- P. Guerriero, S. Tarnburini and P.A. Vigato, Coord. Chem. Rev., 139, 17 (1995); https://doi.org/10.1016/0010-8545(93)01105-7
- P.A. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004); https://doi.org/10.1016/j.cct.2003.09.003
- J.A. McCleverty and T.J. Meyer, Comprehensive Coordination Chemistry II: From Biology to Nanotechnology, Elsevier Science, edn 2 (2003).
- D.J. Bray, J.K. Clegg, L.F. Lindoy and D. Shilter, Adv. Inorg. Chem., 59, 1 (2007); https://doi.org/10.1016/S0898-8838(06)59001-4
- G. Aromi, P. Gamez and J. Reedijk, Coord. Chem. Rev., 252, 964 (2008); https://doi.org/10.1016/j.ccr.2007.07.008
- P.A. Vigato, V. Peruzzo and S. Tamburini, Coord. Chem. Rev., 253, 1099 (2009); https://doi.org/10.1016/j.ccr.2008.07.013
- J.J. Wilson and S.J. Lippard, J. Med. Chem., 55, 5326 (2012); https://doi.org/10.1021/jm3002857
- H.O. Omoregie, N. Obi-Egbedi and J.A.O. Woods, Int. J. Chem., 6, 71 (2014); https://doi.org/10.5539/ijc.v6n1p71
- G. Ahumada, T. Roisnel, S. Kahlal, D. Carrillo, R. Córdova, J.-Y. Saillard, J.-R. Hamon and C. Manzur, Inorg. Chim. Acta, 470, 221 (2018); https://doi.org/10.1016/j.ica.2017.04.050
- H.O. Omoregie, Int. J. Chem., 10, 11 (2018); https://doi.org/10.5539/ijc.v10n4p11
- R.J. Anto, K.N.D. Babu, K.N. Rajasekharan and R. Kuttan, Cancer Lett., 94, 74 (1995).
- R. Karvembu, C. Jayabalakrishnan and K. Natarajan, Transition Met. Chem., 27, 574 (2002); https://doi.org/10.1023/A:1019877128146
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- G. Poncelet, M.A. Centeno and R. Molina, Appl. Catal. A Gen., 288, 232 (2005); https://doi.org/10.1016/j.apcata.2005.04.052
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- V. Alagarsamy, S. Murugesan, K. Dhanabal, M. Muruga and E. De. Clereq, Indian J. Pharm. Sci., 69, 304 (2007); https://doi.org/10.4103/0250-474X.33167
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- P.K. Sahu, P.K. Sahu and D.D. Agarwal, J. Indian Chem. Soc., 92, 169 (2015).
- N. Kumari, P. Khandelwal and Y.C. Joshi, J. Indian Chem. Soc., 91, 1577 (2014).
- I. Rama and S. Ramaswami, J. Indian Chem. Soc., 91, 1877 (2014).
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- C.W. Young, R.B. Duvall and N. Wright, Anal. Chem., 23, 709 (1951); https://doi.org/10.1021/ac60053a007
- I.L. Finar, Organic Chemistry, The English Book Society and Longman Group Ltd., edn 3, vol. 1, p. 284 (1982).
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- N. Sharma, R. Gupta, M. Nagar and R. Bohra, J. Indian Chem. Soc., 91, 1467 (2014).
- D. Kumar, J. Sharma, S. Chandra and A. Shymal, J. Indian Chem. Soc., 90, 1077 (2013).
- R.M. Silverstein, G.C. Bassley and T.C. Morrill, Spectrometric Identification of Organic Compound, Wiley: Singapore, edn 5 (1991).
- P.P. Kalbende, A.B. Zade and M.V. Tarase, J. Indian Chem. Soc., 99, 611 (2013).
- R.S. Ghadwal and A. Singh, J. Indian Chem. Soc., 91, 2051 (2014).
- K. Nakamoto, C. Udovich and J. Takemoto, J. Am. Chem. Soc., 92, 3973 (1970); https://doi.org/10.1021/ja00716a024
- I.C. Shukla, V. Kumar and O.P. Yadav, J. Indian Chem. Soc., 91, 829 (2014).
- M.L.H. Nair and A.S. Appukuttan, J. Indian Chem. Soc., 91, 393 (2014).
- J. Chakarvorty and B. Sahu, Indian J. Chem., 19A, 441 (1980).
- P.K. Das, A.K. Panda, N.K. Behera and S.K. Tripathi, J. Indian Chem. Soc., 91, 1867 (2014).
- K. Nakamoto, Infrared Spectra of Inorganic and Coordinated Compounds, John Wiley, New York, p. 156 (1963).
- G.L. Cook and F.M. Church, J. Phys. Chem., 61, 458 (1957); https://doi.org/10.1021/j150550a017
- R. Rani, R. Ranjan and N.C. Bhattacharji, J. Indian Chem. Soc., 85, 479 (2008).
- A. Joseph, B. Joseph and B. Narayna, J. Indian Chem. Soc., 85, 479 (2008).
- K.C. Dutta, P.C. Reddy, M. Kote, T. Reddy, M. Tambe and M. Mitra, Asian J. Chem., 23, 4511 (2011).
- P. Kumari, S. Prakash and D. Prakash, J. Indian Chem. Soc., 89, 1923 (2012).
- A.B.P. Lever, Inorganic Spectroscopy, Elsevier: Amsterdam-OxfordNew York-Tokyo, edn 2, p. 70 (1984).
- B.K. Rai, V. Singh, S. Vidyarthi and P. Sinha, Asian J. Chem., 23, 4638 (2011).
- O.B. Chanu, R.B. Thakur, A. Koch, R.A. Lal and A. Kumar, J. Indian Chem. Soc., 90, 543 (2013).
- D. Kumar, N. Sharma and S. Chadda, J. Indian Chem. Soc., 93, 1343 (2016).
- G.J. Tortora, B.R. Funke and C.L. Case, Microbiology-An Introduction, Benzamin Cummings: California, edn 10 (2009).
- D. Kumar and Neelam, J. Indian Chem. Soc., 92, 319 (2015).
References
P. Guerriero, S. Tarnburini and P.A. Vigato, Coord. Chem. Rev., 139, 17 (1995); https://doi.org/10.1016/0010-8545(93)01105-7
P.A. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004); https://doi.org/10.1016/j.cct.2003.09.003
J.A. McCleverty and T.J. Meyer, Comprehensive Coordination Chemistry II: From Biology to Nanotechnology, Elsevier Science, edn 2 (2003).
D.J. Bray, J.K. Clegg, L.F. Lindoy and D. Shilter, Adv. Inorg. Chem., 59, 1 (2007); https://doi.org/10.1016/S0898-8838(06)59001-4
G. Aromi, P. Gamez and J. Reedijk, Coord. Chem. Rev., 252, 964 (2008); https://doi.org/10.1016/j.ccr.2007.07.008
P.A. Vigato, V. Peruzzo and S. Tamburini, Coord. Chem. Rev., 253, 1099 (2009); https://doi.org/10.1016/j.ccr.2008.07.013
J.J. Wilson and S.J. Lippard, J. Med. Chem., 55, 5326 (2012); https://doi.org/10.1021/jm3002857
H.O. Omoregie, N. Obi-Egbedi and J.A.O. Woods, Int. J. Chem., 6, 71 (2014); https://doi.org/10.5539/ijc.v6n1p71
G. Ahumada, T. Roisnel, S. Kahlal, D. Carrillo, R. Córdova, J.-Y. Saillard, J.-R. Hamon and C. Manzur, Inorg. Chim. Acta, 470, 221 (2018); https://doi.org/10.1016/j.ica.2017.04.050
H.O. Omoregie, Int. J. Chem., 10, 11 (2018); https://doi.org/10.5539/ijc.v10n4p11
R.J. Anto, K.N.D. Babu, K.N. Rajasekharan and R. Kuttan, Cancer Lett., 94, 74 (1995).
R. Karvembu, C. Jayabalakrishnan and K. Natarajan, Transition Met. Chem., 27, 574 (2002); https://doi.org/10.1023/A:1019877128146
S.M. Jadhav, V.A. Shelke, A.S. Munde, S.G. Shankarwar, S.G. Patharkar and T.K. Chondhekar, J. Coord. Chem., 63, 4153 (2010); https://doi.org/10.1080/00958972.2010.529136
B. Marciniak and G.E. Buono-Core, J. Photochem. Photobiol. Chem. A, 52, 1 (1990); https://doi.org/10.1016/1010-6030(90)87085-P
G. Poncelet, M.A. Centeno and R. Molina, Appl. Catal. A Gen., 288, 232 (2005); https://doi.org/10.1016/j.apcata.2005.04.052
S.K. Bose, B. Brand, H.O. Omoregie, M. Haehnol, G. Bringmann, J. Maier and T.B. Marder, ACS Catal., 6, 8332 (2016); https://doi.org/10.1021/acscatal.6b02918
J. do Couto-Almeida, D.A. Paixão, I.M. Marzano, J. Ellena, M. Pivatto, N.P. Lopes, A.M.D.C. Ferreira, E.C. Pereira-Maia, S. Guilardi and W. Guerra, Polyhedron, 89, 1 (2015); https://doi.org/10.1016/j.Poly.2014.12.026
V. Alagarsamy, V.R. Solomon and M. Murugan, Bioorg. Med. Chem., 15, 4009 (2007); https://doi.org/10.1016/j.bmc.2007.04.001
N.G. Kozlov, L.I. Basalaeva, S.I. Firgang and A.S. Shashkov, Russ. J. Org. Chem., 40, 518 (2004); https://doi.org/10.1023/B:RUJO.0000036073.49961.28
C. Simon, T. Constantieux and J. Rodriguez, Eur. J. Org. Chem., 4957 (2004); https://doi.org/10.1002/ejoc.200400511
V. Alagarsamy, S. Murugesan, K. Dhanabal, M. Muruga and E. De. Clereq, Indian J. Pharm. Sci., 69, 304 (2007); https://doi.org/10.4103/0250-474X.33167
V. Haridas, K. Lal and Y.K. Sharma, Tetrahedron Lett., 48, 4719 (2007); https://doi.org/10.1016/j.tetlet.2007.05.023
P.K. Sahu, P.K. Sahu and D.D. Agarwal, J. Indian Chem. Soc., 92, 169 (2015).
N. Kumari, P. Khandelwal and Y.C. Joshi, J. Indian Chem. Soc., 91, 1577 (2014).
I. Rama and S. Ramaswami, J. Indian Chem. Soc., 91, 1877 (2014).
B.B. Mahapatra, A.K. Sarangi and R.R. Mishra, J. Indian Chem. Soc., 93, 9 (2016).
K. Nakanishi, Infrared Absorption Spectroscopy, Holden-Day Inc., San Francisco and Nankodo Company Limited, Tokyo, edn 2, p. 213 (1964).
J.R. Ferraro, Lower Frequency Vibrations of Inorganic and Coordination Compounds, Plenum, New York (1971).
A.R. Katritzky and A.P. Ambler, Physical Methods of Heterocyclic Chemistry, Academic Press: New York, vol. II (1963).
M.K. Singh, A.D.R. Laksar, B. Paul and J. Paul, J. Indian Chem. Soc., 85, 485 (2008).
C.W. Young, R.B. Duvall and N. Wright, Anal. Chem., 23, 709 (1951); https://doi.org/10.1021/ac60053a007
I.L. Finar, Organic Chemistry, The English Book Society and Longman Group Ltd., edn 3, vol. 1, p. 284 (1982).
L.J. Bellamy, The Infrared Spectra of Complex Molecules, Chapman & Hall: London, edn 3, pp 160-161 (1975).
B.B. Mahapatra and A.K. Sarangi, J. Indian Chem. Soc., 86, 559 (2009).
D. Kumar, A. Shymal, A. Kumar, P.K. Gupta and D. Das, J. Indian Chem. Soc., 87, 417 (2010).
M.K. Rahangale, A.R. Yaul, G.B. Pethe and A.S. Ashwar, J. Indian Chem. Soc., 91, 1891 (2014).
R. Jain, A.K. Rai and R.C. Mehrotra, Inorg. Chim. Acta, 126, 99 (1987); https://doi.org/10.1016/S0020-1693(00)81247-5
R. Bohra, A. Dhammani, R.K. Sharma and R.C. Mehrotra, Synth. React. Inorg. Met.-Org. Chem., 31, 681 (2001); https://doi.org/10.1081/SIM-100104796
N. Sharma, R. Gupta, M. Nagar and R. Bohra, J. Indian Chem. Soc., 91, 1467 (2014).
D. Kumar, J. Sharma, S. Chandra and A. Shymal, J. Indian Chem. Soc., 90, 1077 (2013).
R.M. Silverstein, G.C. Bassley and T.C. Morrill, Spectrometric Identification of Organic Compound, Wiley: Singapore, edn 5 (1991).
P.P. Kalbende, A.B. Zade and M.V. Tarase, J. Indian Chem. Soc., 99, 611 (2013).
R.S. Ghadwal and A. Singh, J. Indian Chem. Soc., 91, 2051 (2014).
K. Nakamoto, C. Udovich and J. Takemoto, J. Am. Chem. Soc., 92, 3973 (1970); https://doi.org/10.1021/ja00716a024
I.C. Shukla, V. Kumar and O.P. Yadav, J. Indian Chem. Soc., 91, 829 (2014).
M.L.H. Nair and A.S. Appukuttan, J. Indian Chem. Soc., 91, 393 (2014).
J. Chakarvorty and B. Sahu, Indian J. Chem., 19A, 441 (1980).
P.K. Das, A.K. Panda, N.K. Behera and S.K. Tripathi, J. Indian Chem. Soc., 91, 1867 (2014).
K. Nakamoto, Infrared Spectra of Inorganic and Coordinated Compounds, John Wiley, New York, p. 156 (1963).
G.L. Cook and F.M. Church, J. Phys. Chem., 61, 458 (1957); https://doi.org/10.1021/j150550a017
R. Rani, R. Ranjan and N.C. Bhattacharji, J. Indian Chem. Soc., 85, 479 (2008).
A. Joseph, B. Joseph and B. Narayna, J. Indian Chem. Soc., 85, 479 (2008).
K.C. Dutta, P.C. Reddy, M. Kote, T. Reddy, M. Tambe and M. Mitra, Asian J. Chem., 23, 4511 (2011).
P. Kumari, S. Prakash and D. Prakash, J. Indian Chem. Soc., 89, 1923 (2012).
A.B.P. Lever, Inorganic Spectroscopy, Elsevier: Amsterdam-OxfordNew York-Tokyo, edn 2, p. 70 (1984).
B.K. Rai, V. Singh, S. Vidyarthi and P. Sinha, Asian J. Chem., 23, 4638 (2011).
O.B. Chanu, R.B. Thakur, A. Koch, R.A. Lal and A. Kumar, J. Indian Chem. Soc., 90, 543 (2013).
D. Kumar, N. Sharma and S. Chadda, J. Indian Chem. Soc., 93, 1343 (2016).
G.J. Tortora, B.R. Funke and C.L. Case, Microbiology-An Introduction, Benzamin Cummings: California, edn 10 (2009).
D. Kumar and Neelam, J. Indian Chem. Soc., 92, 319 (2015).