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Synthesis and Characterization of Mannich Aminomethylation Products of Metal(alaninato) Complexes Using 1-Nitropropane as Carbon Acid
Corresponding Author(s) : S. Supriya
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
Mannich aminomethylation products have been synthesized by one-pot template condensation reaction of bis(alaninato)metal(II) complexes, M(aa)2, with formaldehyde and 1-nitropropane. The DL-isomer and the L-isomer of the metal(alaninato) complexes of Cu(II), Ni(II) and Zn(II) were used separately for the synthesis of Mannich aminomethylation products in order to study the differential reactivities of the stereoisomers of the complexes. Differential reactivities were observed for the isomers in the form of different products isolated at the end of the reaction. Role of pH in Mannich aminomethylation reaction was studied by carrying out the reactions under acidic (pH = 4-5) and basic (pH = 9) conditions. The synthesized complexes were characterized by elemental analysis, ESI mass analysis, UV, IR, NMR and ESR.
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- Y. Shimazaki, M. Takani and O. Yamauchi, J. Chem. Soc., Dalton Trans., 7854 (2009); doi:10.1039/b905871k.
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- A. Barnea and G. Cho, Endocrinology, 115, 936 (1984); doi:10.1210/endo-115-3-936.
- V.B. Valodkar, G.L. Tembe, R.N. Ram and H.S. Rama, Catal. Lett., 90, 91 (2003); doi:10.1023/A:1025828629486.
- (a) A. Puzari and J.B. Baruah, React. Funct. Polym., 47, 147 (2001); doi:10.1016/S1381-5148(01)00024-4; (b) P.K. Sahoo, M. Dey and S.K. Swain, J. Appl. Polym. Sci., 74, 2785 (1999); doi:10.1002/(SICI)1097-4628(19991213)74:12<2785::AID-APP1>3.0.CO;2-X.
- S. Supriya, A. Raghavan, V.R. Vijayaraghavan, K. Chinnakali, H.-K. Fun and J. Subramanian, Polyhedron, 26, 3217 (2007); doi:10.1016/j.poly.2007.02.017.
- (a) S. Supriya, A. Raghavan, V.R. Vijayaraghavan and J. Subramanian, Polyhedron, 26, 3388 (2007); doi:10.1016/j.poly.2007.03.018; (b) P. Comba, T.W. Hambley, G.A. Lawrence, L.L. Martin, P. Renold and K. Varnagy, J. Chem. Soc., Dalton Trans., 277 (1991); doi:10.1039/dt9910000277; (c) C.H. Ng, C.M. Lim, T.M. Chang, S.G. Teoh, S.W. Yap and S.W. Ng, Polyhedron, 25, 1287 (2006); doi:10.1016/j.poly.2005.08.052.
- N. Arulsamy, B. Srinivas and P.S. Zacharias, Transition Met. Chem., 15, 309 (1990); doi:10.1007/BF01061940.
- C.R.K. Rao, N. Arulsamy, P.S. Zacharias and D.J. Hodgson, J. Chem. Soc., Dalton Trans., 3581 (1993); doi:10.1039/dt9930003581.
- F.E. Mabbs and D. Collison, EPR of Transition Metal Compounds, Elsevier, Amsterdam, p. 379 (1992).
- U. Sakaguchi and A.W. Addison, J. Chem. Soc., Dalton Trans., 600 (1979); doi:10.1039/dt9790000600.
References
Y. Shimazaki, M. Takani and O. Yamauchi, J. Chem. Soc., Dalton Trans., 7854 (2009); doi:10.1039/b905871k.
(a) R.D. Hancock and A.E. Martell, Chem. Rev., 89, 1875 (1989); doi:10.1021/cr00098a011; (b) P.V. Bernhardt and G.A. Lawrance, Coord. Chem. Rev., 104, 297 (1990); doi:10.1016/0010-8545(90)80045-U.
A. Barnea and G. Cho, Endocrinology, 115, 936 (1984); doi:10.1210/endo-115-3-936.
V.B. Valodkar, G.L. Tembe, R.N. Ram and H.S. Rama, Catal. Lett., 90, 91 (2003); doi:10.1023/A:1025828629486.
(a) A. Puzari and J.B. Baruah, React. Funct. Polym., 47, 147 (2001); doi:10.1016/S1381-5148(01)00024-4; (b) P.K. Sahoo, M. Dey and S.K. Swain, J. Appl. Polym. Sci., 74, 2785 (1999); doi:10.1002/(SICI)1097-4628(19991213)74:12<2785::AID-APP1>3.0.CO;2-X.
S. Supriya, A. Raghavan, V.R. Vijayaraghavan, K. Chinnakali, H.-K. Fun and J. Subramanian, Polyhedron, 26, 3217 (2007); doi:10.1016/j.poly.2007.02.017.
(a) S. Supriya, A. Raghavan, V.R. Vijayaraghavan and J. Subramanian, Polyhedron, 26, 3388 (2007); doi:10.1016/j.poly.2007.03.018; (b) P. Comba, T.W. Hambley, G.A. Lawrence, L.L. Martin, P. Renold and K. Varnagy, J. Chem. Soc., Dalton Trans., 277 (1991); doi:10.1039/dt9910000277; (c) C.H. Ng, C.M. Lim, T.M. Chang, S.G. Teoh, S.W. Yap and S.W. Ng, Polyhedron, 25, 1287 (2006); doi:10.1016/j.poly.2005.08.052.
N. Arulsamy, B. Srinivas and P.S. Zacharias, Transition Met. Chem., 15, 309 (1990); doi:10.1007/BF01061940.
C.R.K. Rao, N. Arulsamy, P.S. Zacharias and D.J. Hodgson, J. Chem. Soc., Dalton Trans., 3581 (1993); doi:10.1039/dt9930003581.
F.E. Mabbs and D. Collison, EPR of Transition Metal Compounds, Elsevier, Amsterdam, p. 379 (1992).
U. Sakaguchi and A.W. Addison, J. Chem. Soc., Dalton Trans., 600 (1979); doi:10.1039/dt9790000600.