Organometallic 1,5-benzodiazepine and 1,5-benzodiaze pinium compounds: Synthesis, characterization, x-ray diffraction structures and theoretical investigation
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CRISTINA GALLARDO [1] ; ALEXANDER TRUJILLO [1] ; MAURICIO FUENTEALBA [1] ; ANDRES VEGA [2] ; DAVID CARRILLO [1] ; CAROLINA MANZUR [1]
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[1] Pontificia Universidad Católica de Valparaíso
Pontificia Universidad Católica de Valparaíso
Valparaíso, Chile
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[2] Universidad Nacional Andrés Bello Facultad de Ecología y Recursos Naturales
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- Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 52, Nº. 3, 2007, págs. 1266-1270
- Idioma: inglés
- Enlaces
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Resumen
The organometallic tridentate ketoamine or enaminone compound, (η5-Cp)Fe(η5-C J H4)-C(=0)-CH=C(Me)-NH-C6H4-o-NH2, undergoes an intramolecular cyclocondensation promoted by Cu(C10(4))2-6H(2)0 (2:1 molar ratio) affording the neutral 2-ferrocenyl-4-methyl-1,5-benzodiazepine, 1. However, when the molar ratio used is 1:1, the ketoamine or enaminone compound transforms into the 2-ferrocenyl-4-methyl-1,5-benzodiazepinium cation, [2]+. The X-ray molecular structure of 1 exhibits a seven-membered ring with a boat conformation, and two folding dihedral angles along the N(l)-N(2) and C(11)-C(13) axes. In the case of [2]+, the structure shows only one folding dihedral angle along the N(l)-N(2) axis. A rationalization of the properties of 1 and [2]+ is provided through DFT calculations
