Abstract
An ionic liquid-supported Schiff base 1-{2-(2-hydroxy-5-chlorobenzylamine) ethyl}-3-methylimidazolium tetrafluoroborate and its Co(II), Ni(II), Cu(II), Mn(III), Fe(III) and Cr(III) complexes were synthesized and characterized by various analytical (elemental analysis, molar conductance and magnetic susceptibility measurements) and spectroscopic (PXRD, SEM, ESI-MS, UV-Visible, FT-IR, \(^{ 1}\hbox {H NMR}\) and \(^{13}\hbox {C-NMR}\)) methods. Based on these spectral data and spectra, tetra coordinated and hexacoordinated geometries were assigned for the synthesized metal complexes. Molar conductance of the complexes showed their (1:2) electrolytic nature. The Schiff base ligand and its complexes were screened for in vitro antimicrobial activities against some naturally available gram positive and gram negative bacteria to assess their inhibition potentials. Maximum inhibition zone was produced by the Cu(II) complex (5a) in plates of Klebsiella pneumoniae while the minimum inhibition zone was produced by in plates of Bacillus cereus.
Graphical abstract
Transition metal complexes synthesized from an ionic liquid-supported Schiff base have been characterized by various spectroscopic and analytical techniques. Based on the experimental data, it was suggested that the metal ions be coordinated by the ligand in 1:2 ratio. The complexes were explored against Gram-positive and Gram-negative bacteria.
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Anastas P T, Kirchhoff M M and Williamson T C 2001 Catalysis as a foundational pillar of green chemistry Appl. Catal. A 221 3
Rogers R D and Seddon K R 2003 Ionic Liquids–Solvents of the Future? Science 302 792
Sheldon R A 2012 Fundamentals of green chemistry: efficiency in reaction design Chem. Soc. Rev. 41 1437
Dupont J, de Souza R F and Suarez P A Z 2002 Ionic liquid (molten salt) phase organometallic catalysis Chem. Rev. 102 3667
Seddon K R 1997 Ionic liquids for clean technology J. Chem. Technol. Biotechnol. 68 351
Welton T 1999 Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem. Rev. 99 2071
Gordon C M 2001 New developments in catalysis using ionic liquids Appl. Catal. Gen. A 222 101
Jain N, Kumar A, Chauhan S and Chauhan S M S 2005 Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid: biomimetic models of nitric oxide synthase Tetrahedron 61 1015
Wasserscheid P and Welton T 2008 Ionic Liquid in Synthesis \(2^{{\rm nd}}\) edn. (Weinheim: Wiley-VCH)
Zhao H and Malhotra S V 2002 Applications of Ionic Liquids in Organic Synthesis Aldrichim. Acta 35 75
Endres F, Welton T and Wasserscheid P 2003 Ionic Liquids in Synthesis (Weinheim: Wiley-VCH) pp. 289-318
Husum T L, Jorgensen C T, Christensen M W and Kirk O 2001 Enzyme catalysed synthesis in ambient temperature ionic liquids Biocatal. Biotransform. 19 331
Kragl U, Eckstein M and Kaftzik N 2002 Enzyme catalysis in ionic liquids Curr. Opin. Biotechnol. 13 565
Park S and Kazlauskas R J 2003 Biocatalysis in ionic liquids—advantages beyond green technology Curr. Opin. Biotechnol. 14 432
Sheldon R A, Lau R M, Sorgedrager M J, van Rantwijk F and Seddon K R 2002 Biocatalysis in ionic liquids Green Chem. 4 147
Van Rantwijk F and Sheldon R A 2007 Biocatalysis in ionic liquids Chem. Rev. 107 2757
Kubisa P 2004 Application of ionic liquids as solvents for polymerization processes Prog. Polymer Sci. 29 3
Carmichael A J and Haddleton D M 2003 Polymer Synthesis in Ionic Liquids (Weinheim: Wiley-VCH) pp. 319-335
Zhao H, Xia S and Ma P 2005 Use of ionic liquids as ‘green’ solvents for extractions J. Chem. Technol. Biotechnol. 80 1089
Zhao H 2006 Innovative applications of ionic liquids as “green” engineering liquids Chem. Eng. Commun. 193 1660
Moniruzzaman M and Goto M 2011 Ionic liquids: future solvents and reagents for pharmaceuticals J. Chem. Eng. Jpn. 44 370
Siodmiak T, Marszall M P and Proszowska A 2012 Ionic liquids: a new strategy in pharmaceutical synthesis Mini-Rev. Org. Chem. 9 203
Li J, Peng Y and Song G 2005 Mannich reaction catalyzed by carboxyl-functionalized ionic liquid in aqueous media Catal. Lett. 102 159
Davis Jr. J H, Forrester K J T and Merrigan J 1998 Novel organic ionic liquids (OILs) incorporating cations derived from the antifungal drug miconazole Tetrahedron Lett. 49 8955
Jodry J J and Mikami J K 2004 New chiral imidazolium ionic liquids: 3D-network of hydrogen bonding Tetrahedron Lett. 45 4429
Fei Z, Geldbach T J, Zhao D and Dyson P J 2006 From dysfunction to bis-function: on the design and applications of functionalised ionic liquids J. Eur. Chem. 12 2122
Lee S 2006 Functionalized imidazolium salts for task-specific ionic liquids and their applications Chem. Commun. 1049
Kwiatkowski E and Kwiatkowski M 1986 A novel unsymmetrical quadridentate ligand 1-(\(2^\prime \)-aminophenyl)-6-methyl-2,5-diazanona-l,6-diene-8-one and its complexes with copper(II), nickel(II) and palladium(II) Inorg. Chim. Acta 117 145
Holm R H, Everett G W Jr and Chakravorty A 1966 Metal complexes of Schiff bases and \(\upbeta \)-ketoamines Inorg. Chem. 7 83
Daneshvar N, Entezami A A, Khandar A A and Saghatforoush L A 2003 Synthesis and characterization of copper(II) complexes with dissymmetric tetradentate Schiff base ligands derived from aminothioether pyridine, Crystal structures of \([\text{ Cu(pytIsal) }]\text{ ClO }_{4}\cdot 0.5\text{ CH }_{3}\text{ OH }\) and \([\text{ Cu(pytAzosal) }]\text{ ClO }_{4}\) Polyhedron 22 1437
Boghaei D M and Mohebi S 2002 Non-symmetrical tetradentate vanadyl Schiff base complexes derived from 1,2-phenylene diamine and 1,3-naphthalene diamine as catalysts for the oxidation of cyclohexene Tetrahedron 58 5357
Song G, Cai Y and Peng Y 2005 Amino-functionalized ionic liquid as a nucleophilic scavenger in solution phase combinatorial synthesis J. Comb. Chem. 7 561
Su P W, Yang C H, Yang J F, Su P Y and Chuang L Y 2015 Antibacterial activities and antibacterial mechanism of polygonum cuspidatum extracts against nosocomial drug-resistant pathogens Molecules 20 11119
Yıldız M, Kılıc Z and Hökelek T 1998 Intramolecular hydrogen bonding and tautomerism in Schiff bases, Structure of 1,8-di[N-2-oxyphenyl-salicylidene]-3,6-dioxaoctane J. Mol. Struct. 441 1
Yeap G -Y, Ha S -T, Ishizawa N, Suda K, Boey P –L and Mahmood W A K 2003 Synthesis, crystal structure and spectroscopic study of parasubstituted 2-hydroxy-3-methoxybenzalideneanilines J. Mol. Struct. 658 87
Abdel-Latif S A, Hassib H B and Issa Y M 2007 Studies on some salicylaldehyde Schiff base derivatives and their complexes with Cr(III), Mn(II), Fe(III), Ni(II) and Cu(II) Spectrochim. Acta Part. 67 950
Wang J, Pei Y, Zhao Y and Hu Z 2005 Recovery of amino acids by imidazolium based ionic liquids from aqueous media Green Chem. 196
Han D and Row K H 2010 Recent application of ionic liquids in separation technology Molecules 15 2405
Kohawole G A and Patel K S 1981 The stereochemistry of oxovanadium(IV) complexes derived from salicylaldehyde and polymethylenediamines J. Chem. Soc. Dalton Trans. 6 1241
Mahmoud M A, Zaitone S A, Ammar A M and Sallam S A 2016 Synthesis, structure and antidiabetic activity of chromium(III) complexes of metformin Schiff-bases J. Mol. Struct. 1108 60
Adams D M 1967 Metal-Ligand and Related Vibrations: A Critical Survey of the Infrared and Raman Spectra of Metallic and Organometallic Compounds (London: Edward Arnold Publishers)
Adly O M I, Taha A and Fahmy S A 2013 Synthesis, spectral characterization, molecular modeling and antimicrobial activity of new potentially \(\text{ N }_{2}\text{ O }_{2}\) Schiff base complexes J. Mol. Struct. 1054 239
Kar N K, Singh M K and Lal R A 2012 Synthesis and spectral studies on heterobimetallic complexes of manganese and ruthenium derived from bis[N-(2-hydroxynaphthalen-1-yl)methylene]oxaloyldihydrazide Arabian J. Chem. 5 67
Li B, Li Y Q, Zheng W J and Zhou M Y 2009 Synthesis of ionic liquid supported Schiff bases Arkivoc. 11 165
Silverstein R M 2005 Spectrometric Identification of Organic Compounds \(7^{{\rm th}}\) edn. (Hoboken: John Wiley & Sons)
Peral F and Gallego E 1997 Self-association of imidazole and its methyl derivatives in aqueous solution: a study by ultraviolet spectroscopy J. Mol. Struct. 415 187
Shakir M, Nasam O S M, Mohamed A K and Varkey S P 1996 Transition metal complexes of 13–14-membered tetraazamacrocycles: synthesis and characterization Polyhedron 15 1283
Chem L S and Cummings S C 1978 Synthesis and characterization of cobalt(II) and some nickel(II) complexes with N,N’-ethylenebis(p-X-benzoylacetone iminato) and N,N’-ethylenebis(p-X-benzoylmonothioacetone iminato) ligands Inorg. Chem. 17 2358
Del Paggio A A and McMillin D R 1983 Substituent effects and the photoluminescence of Cu(PPh\(_3\))\(_2\)(NN)\(_+\) systems Inorg. Chem. 22 691
Natarajan C, Tharmaraj P and Murugesan R 1992 In situ synthesis and spectroscopic studies of copper(II) and nickel(II) complexes of 1-hydroxy-2-naphthylstyrylketoneimines J. Coord. Chem. 26 205
Dehghanpour S, Bouslimani N, Welter R and Mojahed F 2007 Synthesis, spectral characterization, properties and structures of copper(I) complexes containing novel bidentate iminopyridine ligands Polyhedron 26 154
Lever A B P 1984 Inorganic Electronic Spectroscopy \(2^{{\rm nd}}\) edn. (Amsterdam: Elsevier)
Ray S, Konar S, Jana A, Das K, Dhara A, Chatterjee S and Kar S K 2014 Syntheses, crystal structure, spectroscopic and photoluminescence studies of mononuclear copper(II), manganese(II), cadmium(II), and a 1D polymeric Cu(II) complexes with a pyrimidine derived Schiff base ligand J. Mol. Struct. 1058 213
Frunza L, Zgura I, Dittmar A and Fricke R 2005 Embedding Jacobsen manganese(III) salen complex into nanoporous molecular sieves: spectroscopic characterisation of host–guest interactions Adv. Mater. 7 2141
Kulkarni A D, Patil S A and Badami P S 2009 Electrochemical properties of some transition metal complexes: synthesis, characterization and in-vitro antimicrobial studies of Co(II), Ni(II), Cu(II), Mn(II) and Fe(III) complexes Int. J. Electrochem. Sci. 4 717
Dey K and Chakraborty K 2000 Synthesis and characterization of some chromium(III) complexes with N, S, O–donor thiohydrazones Indian J. Chem. 39 1140
Acknowledgements
The authors are grateful to the Departmental Special Assistance Scheme under the University Grants Commission, New Delhi (SAP-DRS-III, NO.540/12/DRS/2013) for financial support and SAIF, NEHU, Guwahati, India for \(^{13}\hbox {CNMR}\), \(^{1}\hbox {H NMR}\), ESI-MS and elemental analysis. We are thankful to USIC, NBU, West Bengal, India and Department of Chemistry, Sikkim University, Sikkim, India for SEM and PXRD spectra respectively.
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Sinha, B., Bhattacharya, M. & Saha, S. Transition metal complexes obtained from an ionic liquid-supported Schiff base: synthesis, physicochemical characterization and exploration of antimicrobial activities. J Chem Sci 131, 19 (2019). https://doi.org/10.1007/s12039-019-1593-x
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DOI: https://doi.org/10.1007/s12039-019-1593-x