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Direct Electrochemical Synthesis of Unique Organoaluminium Halides and Their Coordination Complexes at Sacrificial Aluminium Anode
Corresponding Author(s) : Baljit Singh
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
The method of direct electrochemical synthesis of organoaluminium halide involves the electrolysis of organic halide in acetonitrile (as solvent) and tetrabutylammonium chloride (as supporting electrolyte) using sacrificial aluminium anode and platinum cathode in H-type cell. The organic halide is bromoethane, 1-bromopropane, chlorobenzene and cyclopentadiene (Cp). The compounds conveniently isolated are (R)2AlX and AlCp3. On refluxing with nitrogen containing ligand (L) 2,2’-bipyridyl and 1,10-phenanthroline, these organoaluminium halides do not form coordination compounds. However, the coordination compounds with general formula (R)2AlX·L and AlCp3·L have been synthesized electrochemically by addition of these ligand to the electrolysis phase. All these electrochemically synthesized organoaluminium halides have been characterized by physical measurements, elemental analysis and infrared spectroscopic studies. All these electrochemical products are associated with high current efficiencies.
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- M.A. Reynolds, T.B. Rauchfuss and S.R. Wilson, Organometallics, 22, 1619 (2003); https://doi.org/10.1021/om020724e.
- N.A. Bell, W. Clegg, J.R. Creighton and E.S. Raper, Inorg. Chim. Acta, 303, 12 (2000); https://doi.org/10.1016/S0020-1693(99)00487-9.
- P. Starynowicz, Dalton Trans., 7, 825 (2004); https://doi.org/10.1039/B316253B.
- T.-H. Kim and S.-M. Park, Electrochim. Acta, 50, 1461 (2005); https://doi.org/10.1016/j.electacta.2004.10.073.
- J. Tian and K.D. Moeller, Org. Lett., 7, 5381 (2005); https://doi.org/10.1021/ol0519487.
- J.E. Dick and D. Chong, Org. Chem. Curr. Res., 1, 1 (2012); https://doi.org/10.4172/2161-0401.1000e113.
- O.A. Farghaly, R.S. Abdel Hameed and H.A. Abd-Alhakeem, Int. J. Electrochem. Sci., 9, 3287 (2014).
- U. Madhu, N.R. Mukherjee and A. Mondal, Indian J. Pure Appl. Phys., 45, 226 (2007).
- H. Chettah and D. Abdi, Thin Solid Films, 537, 119 (2013); https://doi.org/10.1016/j.tsf.2013.04.024.
- W.J. Ebadi, S.Y. Leng and M.R. Mahmoudian, Int. J. Electrochem. Sci., 7, 8052 (2012).
- A.K. Gupta, R.S. Dubey and J.K. Malik, Int. J. Pharm. Sci. Res., 4, 2450 (2013).
- Y. Zhu, T. Gao, X. Fan, F. Han and C. Wang, Acc. Chem. Res., 50, 1022 (2017); https://doi.org/10.1021/acs.accounts.7b00031.
- D. Grieshaber, R. Mackenzie, J. Voros and E. Reimhult, Sensors, 8, 1400 (2008); https://doi.org/10.3390/s80314000.
- R.K. Ibrahim, S.S. Ahmed, A.N. Naje and A.M. Suhail, Indian J. Appl. Res., 3, 54 (2013); https://doi.org/10.15373/2249555X/MAY2013/188.
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- J.S. Banait and B. Singh, J. Electrochem. Soc. India, 46, 215 (1997).
- J.S. Banait and B. Singh, J. Electrochem. Soc. India, 45, 103 (1996).
- J.S. Banait, B. Singh and S. Rala, J. Indian Chem. Soc., 86, 416 (2009).
- J.S. Banait, B. Singh and H. Kaur, J. Indian Chem. Soc., 82, 555 (2005).
- H. Kaur and B. Singh, E-J. Chem., 9, 381 (2012); https://doi.org/10.1155/2012/403782.
- B. Singh, Shavina and K. Bala, Chem. Sci. Rev. Lett., 3, 367 (2014).
- J.S. Banait and P.K. Pahil, Polyhedron, 5, 1865 (1986); https://doi.org/10.1016/S0277-5387(00)84869-X.
- Vogel’s, Text Book of Practical Organic Chemistry, edn 5 (2004).
- Vogel’s, Text Book of Quantitative Chemical Analysis, Longman Group UK Ltd. (1989).
- M.J. Kappers, M.L. Warddrip and R.F. Hicks, J. Cryst. Growth, 191, 332 (1998); https://doi.org/10.1016/S0022-0248(98)00174-2.
- L. Xia and R.L. McCreery, J. Electrochem. Soc., 146, 3696 (1999); https://doi.org/10.1149/1.1392536.
- R.C. Mehrotra, Organometallic Chemistry, New Age International, New Delhi (2007).
- J. Burt, W. Levason, M.E. Light and G. Reid, Dalton Trans., 43, 14600 (2014); https://doi.org/10.1039/C4DT02051K.
- D. Ridley, Ph.D. Thesis, Synthesis and Spectroscopic Studies on Some Inorganic and Organometallic Compounds, Durham University, UK (1965).
- A. Molter, J. Rust, C.W. Lehmann, G. Deepa, P. Chiba and F. Mohr, Dalton Trans., 40, 9810 (2011); https://doi.org/10.1039/c1dt10885a.
- S.S. Sarwade, W.N. Jadhav, B.C. Khade and D. Tayde, J. Chem. Pharm. Res., 7, 833 (2015).
- D.N. Satyanarayana, Vibrational Spectroscopy. India, New Age International, New Delhi, India (2015).
- S. Saxena, Y.P. Singh and A.K. Rai, J. Organomet. Chem., 270, 301 (1984); https://doi.org/10.1016/0022-328X(84)80377-0.
- Z.A. Siddiqi, I.A. Ansari, F. Sama and M. Shahid, Int. J. Innov. Res. Sci. Eng. Technol., 3, 8673 (2014).
- M.T.H. Tarafder, T.-J. Khoo, K.A. Crouse, A.M. Ali, B.M. Yamin and H.-K. Fun, Polyhedron, 21, 2691 (2002); https://doi.org/10.1016/S0277-5387(02)01272-X.
References
M.A. Reynolds, T.B. Rauchfuss and S.R. Wilson, Organometallics, 22, 1619 (2003); https://doi.org/10.1021/om020724e.
N.A. Bell, W. Clegg, J.R. Creighton and E.S. Raper, Inorg. Chim. Acta, 303, 12 (2000); https://doi.org/10.1016/S0020-1693(99)00487-9.
P. Starynowicz, Dalton Trans., 7, 825 (2004); https://doi.org/10.1039/B316253B.
T.-H. Kim and S.-M. Park, Electrochim. Acta, 50, 1461 (2005); https://doi.org/10.1016/j.electacta.2004.10.073.
J. Tian and K.D. Moeller, Org. Lett., 7, 5381 (2005); https://doi.org/10.1021/ol0519487.
J.E. Dick and D. Chong, Org. Chem. Curr. Res., 1, 1 (2012); https://doi.org/10.4172/2161-0401.1000e113.
O.A. Farghaly, R.S. Abdel Hameed and H.A. Abd-Alhakeem, Int. J. Electrochem. Sci., 9, 3287 (2014).
U. Madhu, N.R. Mukherjee and A. Mondal, Indian J. Pure Appl. Phys., 45, 226 (2007).
H. Chettah and D. Abdi, Thin Solid Films, 537, 119 (2013); https://doi.org/10.1016/j.tsf.2013.04.024.
W.J. Ebadi, S.Y. Leng and M.R. Mahmoudian, Int. J. Electrochem. Sci., 7, 8052 (2012).
A.K. Gupta, R.S. Dubey and J.K. Malik, Int. J. Pharm. Sci. Res., 4, 2450 (2013).
Y. Zhu, T. Gao, X. Fan, F. Han and C. Wang, Acc. Chem. Res., 50, 1022 (2017); https://doi.org/10.1021/acs.accounts.7b00031.
D. Grieshaber, R. Mackenzie, J. Voros and E. Reimhult, Sensors, 8, 1400 (2008); https://doi.org/10.3390/s80314000.
R.K. Ibrahim, S.S. Ahmed, A.N. Naje and A.M. Suhail, Indian J. Appl. Res., 3, 54 (2013); https://doi.org/10.15373/2249555X/MAY2013/188.
H.S. Toh and R.G. Compton, Chemistry Open, 4, 261 (2015); https://doi.org/10.1002/open.201402161.
J.S. Banait and B. Singh, J. Electrochem. Soc. India, 46, 215 (1997).
J.S. Banait and B. Singh, J. Electrochem. Soc. India, 45, 103 (1996).
J.S. Banait, B. Singh and S. Rala, J. Indian Chem. Soc., 86, 416 (2009).
J.S. Banait, B. Singh and H. Kaur, J. Indian Chem. Soc., 82, 555 (2005).
H. Kaur and B. Singh, E-J. Chem., 9, 381 (2012); https://doi.org/10.1155/2012/403782.
B. Singh, Shavina and K. Bala, Chem. Sci. Rev. Lett., 3, 367 (2014).
J.S. Banait and P.K. Pahil, Polyhedron, 5, 1865 (1986); https://doi.org/10.1016/S0277-5387(00)84869-X.
Vogel’s, Text Book of Practical Organic Chemistry, edn 5 (2004).
Vogel’s, Text Book of Quantitative Chemical Analysis, Longman Group UK Ltd. (1989).
M.J. Kappers, M.L. Warddrip and R.F. Hicks, J. Cryst. Growth, 191, 332 (1998); https://doi.org/10.1016/S0022-0248(98)00174-2.
L. Xia and R.L. McCreery, J. Electrochem. Soc., 146, 3696 (1999); https://doi.org/10.1149/1.1392536.
R.C. Mehrotra, Organometallic Chemistry, New Age International, New Delhi (2007).
J. Burt, W. Levason, M.E. Light and G. Reid, Dalton Trans., 43, 14600 (2014); https://doi.org/10.1039/C4DT02051K.
D. Ridley, Ph.D. Thesis, Synthesis and Spectroscopic Studies on Some Inorganic and Organometallic Compounds, Durham University, UK (1965).
A. Molter, J. Rust, C.W. Lehmann, G. Deepa, P. Chiba and F. Mohr, Dalton Trans., 40, 9810 (2011); https://doi.org/10.1039/c1dt10885a.
S.S. Sarwade, W.N. Jadhav, B.C. Khade and D. Tayde, J. Chem. Pharm. Res., 7, 833 (2015).
D.N. Satyanarayana, Vibrational Spectroscopy. India, New Age International, New Delhi, India (2015).
S. Saxena, Y.P. Singh and A.K. Rai, J. Organomet. Chem., 270, 301 (1984); https://doi.org/10.1016/0022-328X(84)80377-0.
Z.A. Siddiqi, I.A. Ansari, F. Sama and M. Shahid, Int. J. Innov. Res. Sci. Eng. Technol., 3, 8673 (2014).
M.T.H. Tarafder, T.-J. Khoo, K.A. Crouse, A.M. Ali, B.M. Yamin and H.-K. Fun, Polyhedron, 21, 2691 (2002); https://doi.org/10.1016/S0277-5387(02)01272-X.