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A Novel Pyridazinium Ionic Liquid: Ultrasound Synthesis, Characterization and its Analytical Application Using Cyclic Voltammetry and High Performance Liquid Chromatography
Corresponding Author(s) : Ali F. Alghamdi
Asian Journal of Chemistry,
Vol. 28 No. 6 (2016): Vol 28 Issue 6
Abstract
Synthesis of 1-(3-phenylpropyl)pyridazin-1-ium bromide (2), a novel ionic liquid (IL), was achieved using an efficient, green ultrasound-assisted process. The structure was characterized by FT-IR, 1H NMR, 13C NMR and mass spectrometry. The cyclic voltammetric behaviour of this new ionic liquid 2 (5 × 10-5 mol L-1 and 50 mV/s scan rate) was investigated in Britton-Robinson (B-R), acetate and phosphate buffers at pH 3. A broad cathodic cyclic voltammetric peak at E1/2 = -780 mV was recorded using hanging mercury drop, glassy carbon and graphite electrodes vs. Ag/AgCl reference electrode. Electrochemical reduction of the analyte was irreversible and diffusion-controlled. High performance liquid chromatography (HPLC) of 2 was investigated using a C-18 (5 μm) column for separation from interferences. A mobile phase containing methanol:acetonitrile:phosphate buffer at pH 3 (30:30:40 v/v/v %) was used and elution of 2 was monitored with UV detection at 254 nm. The retention time of this compound was recorded to be 2.152 min.
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- P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, Germany, (2002).
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References
R.D. Rogers and K. Seddon, Ionic Liquids: Industrial Applications for Green Chemistry, ACS Ser. 818, Oxford University Press (2002).
P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, Germany, (2002).
K. Seddon and A. Stark, Green Chem., 4, 119 (2002); doi:10.1039/b111160b.
M.J. Earle and K.R. Seddon, Pure Appl. Chem., 72, 1391 (2000); doi:10.1351/pac200072071391.
R. Sheldon, Chem. Commun., 8, 2399 (2001); doi:10.1039/b107270f.
J.S. Wilkes, J. Mol. Catal. Chem., 214, 11 (2004); doi:10.1016/j.molcata.2003.11.029.
J. Liu, G. Jiang, Y. Chi, Y. Cai, Q. Zhou and J. Hu, Anal. Chem., 75, 5870 (2003); doi:10.1021/ac034506m.
J.H. Wang, D.H. Cheng, X.Y. Chen, Z. Du and Z.L. Fang, Anal. Chem., 79, 620 (2007); doi:10.1021/ac061145c.
Y.F. Lin and I.W. Sun, Electrochim. Acta, 44, 2771 (1999); doi:10.1016/S0013-4686(99)00003-1.
M.A. Ibrahim and M. Messali, Products Finishing, 76, 14 (2011).
S. Takahashi, N. Koura, S. Kohara, M.L. Saboungi and L.A. Curtiss, Plasma Ions, 2, 91 (1999); doi:10.1016/S1288-3255(99)00105-7.
F. Endres, ChemPhysChem, 3, 144 (2002); doi:10.1002/1439-7641(20020215)3:2<144::AID-CPHC144>3.0.CO;2-#.
M. Messali, J. Mater. Environ. Sci., 2, 174 (2011).
A. Zarrouk, M. Messali, H. Zarrok, R. Salghi, A. Al-Sheikh, B. Hammouti, S. Al-Deyab and F. Bentiss, Int. J. Electrochem. Sci., 7, 6998 (2012).
A. Zarrouk, M. Messali, M. Aouad, H. Zarrok, R. Salghi, B. Hammouti, A. Chetouani and S. Al-Deyab, J. Chem. Pharm. Res., 4, 3427 (2012).
L. Moens, D.M. Blake, D.L. Rudnicki and M.J. Hale, J. Sol. Energy Eng., 125, 112 (2003); doi:10.1115/1.1531644.
B. Buszewski and S. Studzinska, Chromatographia, 68, 1 (2008); doi:10.1365/s10337-008-0662-y.
E.G. Yanes, S.R. Gratz, M.J. Baldwin, S.E. Robison and A.M. Stalcup, Anal. Chem., 73, 3838 (2001); doi:10.1021/ac010263r.
Z.S. Breitbach and D.W. Armstrong, Anal. Bioanal. Chem., 390, 1605 (2008); doi:10.1007/s00216-008-1877-3.
Y.N. Hsieh, R.S. Horng, W.Y. Ho, P.C. Huang, C.Y. Hsu, T.J. Whang and C.H. Kuei, Chromatographia, 67, 413 (2008); doi:10.1365/s10337-008-0531-8.
A.J. Bard and L.R. Faulkner, Electrochemical Methods: Fundamentals and Applications, John Wiley & Sons, Inc., USA, edn 2, p. 227 (2001).
J. Wang, Analytical electrochemistry, Wiley-VCH, New Jersey, edn 3, p. 29 (2006).
Y. Polyakova, Y.M. Koo and K.H. Row, Rev. Anal. Chem., 26, 1 (2007); doi:10.1515/REVAC.2007.26.2.77.
Y. Polyakova, Y.M. Koo and K.H. Row, Biotechnol. Bioprocess. Eng., 11, 1 (2006); doi:10.1007/BF02931860.
Y. Wang, M. Tian, W. Bi and K.H. Row, Int. J. Mol. Sci., 10, 2591 (2009); doi:10.3390/ijms10062591.
M. Messali and S.A. Ahmed, Green Sustain. Chem., 1, 70 (2011); doi:10.4236/gsc.2011.13012.
M. Messali and M.A. Asiri, J. Mater. Environ. Sci., 4, 770 (2013).
A.F. Al-Ghamdi, M. Messali and S.A. Ahmed, J. Mater. Environ. Sci., 2, 215 (2011).
M. Messali, Arab. J. Chem., 7, 63 (2014); doi:10.1016/j.arabjc.2013.08.023.
M. Messali, M.R. Aouad, A.A. Ali, N. Rezki, T. Ben Hadda and B. Hammouti, Med. Chem. Res., 24, 1387 (2015); doi:10.1007/s00044-014-1211-x.