Ferrocene Containing Chelating Ligands Part 2
Synthesis, characterization, electrochemical behaviour and crystal structure of 2-ferrocenylmethylamino-benzoic acid
Ferrocenecarboxaldehyde reacts with 2-amino-benzoic acid in benzene to give the Schiff base derivative 2-ferrocenyl- methylidenimino-benzoic acid (η 5-C 5H 5)Fe[(η 5-C 5H 4)CH NC 6H 4COOH] (1). 1 is stable as a solid but easily hydrolyzes in solution. Selective hydrogenation of the imine group can be performed using NaBH 4 to obtain the parent amine (η 5- C 5H 5) Fe[(η 5-C 5H 4)CH 2NH& z.sbnd;C 6H 4COOH]. (2). The molecular structure of 2 has been determined by single-crystal X-ray methods. It crystallizes in the space group P2 1/c, a=11.077(9), b =7.430(2), c=19.194(9) Å, β=111.02(4)°, V=1474(2) Å 3, Z=4. Refinement of the structure gave final R factor of 0.038 (R w=0.035) for 1106 unique reflections having F o 2>2.8σ(F o 2). 2 is stable both in the solid state and solution, and a potential chelating N,O-donor ligand containing a ferrocenyl group. A one-electron oxidation process was found by cyclic voltammetry (0.1 M NBu n 4PF 6, CH 2Cl 2) for 1 and 2 at 0.74 and 0.51 V, respectively. © 1993.
A. Benito et al., "Ferrocene Containing Chelating Ligands Part 2," Inorganica Chimica Acta, Elsevier, Jan 1993.
The definitive version is available at http://dx.doi.org/10.1016/S0020-1693(00)83332-0
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© 1993 Elsevier, All rights reserved.