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Abstract
The reaction of the pendant hydroxyethyl group in the planar pentadentate macrocyclic ligand,1,11-bis(2’-hydroxyethyl)-4,8;12,16;17,21-trinitrilo-1,2,10,11-tetraazacyclohenicosa- 2,4,6,9,12,14,18,20-octaene (L2), derived from the condensation of 2,6-pyridinedialdehyde with 6,6’-bis(2’ hydroxyethylhydrazino) -2,2’-bipyridine (L1), has been investigated. Esterification reactions are facile, and the reaction of the hydroxyethyl-substituted macrocycle with thionyl chloride yields a chloroethyl derivative. Metal complexes of the new derivatized macrocyclic ligands L3-6having general formula ML3-6X2.nH2O (M = Mn, Fe, Co, Ni, Cu, Zn) are readily prepared.
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References
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References
SMITH, K.M. 1975. Porphyrins and Metalloporphyrins; Elsevier, Amsterdam.
CONSTABLE, E.C. 1999. Coordination Chemistry of Macrocyclic Compounds, Oxford Science Publications.
CABBINNES, D.K. and MARGERUM, D.W. 1969. Macrocyclic effect on the stability of copper (II) tetramine complexes. J. Amer. Chem. Soc. 91: 6540-6541.
LINDOY, L.F. 1989. The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, Cambridge.
MELSON, G.A. 1979. Coordination Chemistry of Macrocyclic Compounds, Plenum, New York.
ANSELL, C.W.G., LEWIS, J., LIPTROT, M.C., RAITHBY, P.R. and SCHRODER, M. 1982. The stabilization of low oxidation state transition metal complexes. Preparation and electrochemistry of cobalt(II) unsaturated macrocyclic complexes and the stabilization of a cobalt(II) derivative. Crystal and molecular structure of [(Co(II)(L)(CH3OH)2][BF4]2 and [Co(I)(L){P-(OCH3)3Cl}[PF4]. J. Chem. Soc., Dalton Trans.: 1593-1601.
ANSELL, C.W.G., LEWIS, J., RAITHBY, P.R. and O’DONOGHUE, T.D. 1983. Synthesis of a macrocyclic metal complex incorporating peripheral hydroxyethyl tails: the X-ray structure of [Mn(L1)Cl][PF4]. J. Chem. Soc., Dalton Trans.: 177-179.
ANSELL, C.W.G., LEWIS, J., RAITHBY, P.R. and RAMSDEN, J.N. 1982. Synthesis and X-ray structure of a macrocyclic Pentagonal Bipyramidal Complex of Cobalt(II). J. Chem. Soc., Dalton Trans.: 2127-2129.
CHUNG, L.Y., CONSTABLE, E.C., DALE, A.R., KHAN, M.S., LIPTROT, M.C., LEWIS, J. and RAITHBY, P.R. 1990. The transient template effect: chromium(III)-directed synthesis of metal-free macrocyclic ligands and crystal structure of 1,11-bis(2’-hydroxyethyl)-4,8,12,16,17,21-trinitilo-1,2,10,11-tetra-azacyclohenicosa-2,4,6,9,12,14,18,20-octaene hydrochloride tetrahydrate. J. Chem. Soc., Dalton Trans.: 1397-1404.
CHUNG, L.Y., CONSTABLE, E.C., KHAN, M.S., LEWIS, J., RAITHBY, P.R. and VARGAS, M.D. 1984. Structural characterization of a pentagonal bipyramidal macrocyclic chromium(III) complex, an explanation of a chromium-mediated-template effect. J. Chem. Soc., Chem Commun.: 1425-1426.
CONSTABLE, E.C., KHAN, F.K., LEWIS, J., LIPTROT, M.C. and RAITHBY, P.R. 1985. The preparation and coordination chemistry of 2,2’:6’,2”-terpyridine macrocycles. Structural characterization of an intermediate in a transient template reaction. J. Chem. Soc., Dalton Trans.: 333-335.