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Synthesis, Characterization and X-Ray Crystal Structure of Macrocyclic Ligand Based on 2,2-Methylene-bis[(6-formyl)-4-tert-butylphenol] and 1,2-bis-(2-aminoethoxy)ethane
Corresponding Author(s) : Imdad Hussain
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
A new macrocyclic compound based on 2,2-methylene-bis[(6-formyl)-4-tert-butylphenol] and 1,2- bis-(2-aminoethoxy) ethane has been prepared by stirring and refluxing equimolar quantities of ethanolic solution of 2,2-methylene-bis[(6-formyl)-4-tert-butylphenol] and 1,2-bis-(2-aminoethoxy)ethane overnight in a basic media. The synthesis of this macrocyclic ligand involves Schiff-base condensation. This macrocyclic ligand exists in a crystalline solid of yellow colour. The ligand crystallizes in the monoclinic space group P 2(1)/c, with unit cell dimensions, a = 21.2761(17) Å, b = 26.038(2) Å, c = 10.0873(8) Å, a = 90°, b = 93.7090(10)°, g = 90°, Z = 8, V = 5576.6(8) Å3. Unit cell contains 8 molecules of macrocyclic ligand. The macrocyclic ligand was characterized by using single crystal X-ray spectroscopy, 1H NMR, IR-spectroscopy and mass spectrophotometery.
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- H. Okawa, H. Furutachi and D.E. Fenton, Coord. Chem. Rev., 174, 51 (1998); doi:10.1016/S0010-8545(97)00082-9.
- P. Guerriero, S. Tarnburini and P.A. Vigato, Coord. Chem. Rev., 139, 17 (1995); doi:10.1016/0010-8545(93)01105-7.
- P.A. Vigato, S. Tamburini and D.E. Fenton, Coord. Chem. Rev., 106, 25 (1990); doi:10.1016/0010-8545(60)80002-1.
- S.R. Collinson and D.E. Fenton, Coord. Chem. Rev., 148, 19 (1996); doi:10.1016/0010-8545(95)01156-0.
- D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17, 69 (1988); doi:10.1039/cs9881700069.
- P. Zanello, S. Tamburini, P.A. Vigato and G.A. Mazzocchin, Coord. Chem. Rev., 77, 165 (1987); doi:10.1016/0010-8545(87)85034-8.
- S. Brooker, Coord. Chem. Rev., 222, 33 (2001); doi:10.1016/S0010-8545(01)00300-9.
- D.H. Busch, A.L. Vance and A.G. Kolchinski, Comprehensive Supra-molecular Chemistry, Pergamon, New York, vol. 9, pp. 1-42 (1996).
- J.S. Bradshaw, K.E. Krakowiak and R.M. Izatt, Aza-Crown Macrocycles, Wiley, New York, 1993.
- H. Keypour and S. Salehzadeh, Transition Met. Chem., 25, 205 (2000); doi:10.1023/A:1007017400893.
- Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 96, 721 (1996); doi:10.1021/cr9403704.
- F. Vogtle, Comprehensive Supramolecular Chemistry, Pergamon: Oxford, Vol. 2 (1996).
- N.V. Gerbeleu, V.B. Arion and J. Burgess, Template Synthesis of Macrocyclic Compounds; Wiley-VCH: New York (1999).
- V. Yu. Kukushkin, D. Tudela, Y.A. Izotova, V.K. Belsky and A.I. Stash, Polyhedron, 17, 2455 (1998); doi:10.1016/S0277-5387(98)00041-2.
- Bruker, APEX2, GIS, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA (2009).
- G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
- L.J. Farrugia, J. Appl. Cryst., 32, 837 (1999); doi:10.1107/S0021889899006020.
- G.M. Sheldrick, SADABS-Bruker AXS Scaling and Absorption Correction, Bruker AXS Inc., Madison (2008).
- K. Brandenburg, Diamond-Crystal and Molecular Structure Visualization, v. 3.2g. Crystal Impact GbR, Bonn (2011).
- J.D. Dunitz, P. Seiler and R.P. Phizackerley, Acta Crystallogr. B, 30, 2739 (1974); doi:10.1107/S0567740874007928.
References
H. Okawa, H. Furutachi and D.E. Fenton, Coord. Chem. Rev., 174, 51 (1998); doi:10.1016/S0010-8545(97)00082-9.
P. Guerriero, S. Tarnburini and P.A. Vigato, Coord. Chem. Rev., 139, 17 (1995); doi:10.1016/0010-8545(93)01105-7.
P.A. Vigato, S. Tamburini and D.E. Fenton, Coord. Chem. Rev., 106, 25 (1990); doi:10.1016/0010-8545(60)80002-1.
S.R. Collinson and D.E. Fenton, Coord. Chem. Rev., 148, 19 (1996); doi:10.1016/0010-8545(95)01156-0.
D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17, 69 (1988); doi:10.1039/cs9881700069.
P. Zanello, S. Tamburini, P.A. Vigato and G.A. Mazzocchin, Coord. Chem. Rev., 77, 165 (1987); doi:10.1016/0010-8545(87)85034-8.
S. Brooker, Coord. Chem. Rev., 222, 33 (2001); doi:10.1016/S0010-8545(01)00300-9.
D.H. Busch, A.L. Vance and A.G. Kolchinski, Comprehensive Supra-molecular Chemistry, Pergamon, New York, vol. 9, pp. 1-42 (1996).
J.S. Bradshaw, K.E. Krakowiak and R.M. Izatt, Aza-Crown Macrocycles, Wiley, New York, 1993.
H. Keypour and S. Salehzadeh, Transition Met. Chem., 25, 205 (2000); doi:10.1023/A:1007017400893.
Y. Murakami, J. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 96, 721 (1996); doi:10.1021/cr9403704.
F. Vogtle, Comprehensive Supramolecular Chemistry, Pergamon: Oxford, Vol. 2 (1996).
N.V. Gerbeleu, V.B. Arion and J. Burgess, Template Synthesis of Macrocyclic Compounds; Wiley-VCH: New York (1999).
V. Yu. Kukushkin, D. Tudela, Y.A. Izotova, V.K. Belsky and A.I. Stash, Polyhedron, 17, 2455 (1998); doi:10.1016/S0277-5387(98)00041-2.
Bruker, APEX2, GIS, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA (2009).
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
L.J. Farrugia, J. Appl. Cryst., 32, 837 (1999); doi:10.1107/S0021889899006020.
G.M. Sheldrick, SADABS-Bruker AXS Scaling and Absorption Correction, Bruker AXS Inc., Madison (2008).
K. Brandenburg, Diamond-Crystal and Molecular Structure Visualization, v. 3.2g. Crystal Impact GbR, Bonn (2011).
J.D. Dunitz, P. Seiler and R.P. Phizackerley, Acta Crystallogr. B, 30, 2739 (1974); doi:10.1107/S0567740874007928.