Organometallic 1,5-benzodiazepine and 1,5-benzodiaze pinium compounds: Synthesis, characterization, X-ray diffraction structures and theoretical investigation

Cristina Gallardo, Alexander Trujillo, Mauricio Fuentealba, Andres Vega, David Carrillo, Carolina Manzur

Resultado de la investigación: Article

6 Citas (Scopus)

Resumen

The organometallic tridentate ketoamine or enaminone compound, (η5-Cp)Fe(h5-CJH4)-C(=0)-CH= C(Me)-NH-C6H4-o-NH2, undergoes an intramolecular cyclocondensation promoted by Cu(C104) 2-6H20 (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.

Idioma originalEnglish
Páginas (desde-hasta)1266-1270
Número de páginas5
PublicaciónJournal of the Chilean Chemical Society
Volumen52
N.º3
DOI
EstadoPublished - 1 ene 2007

Huella dactilar

Organometallics
Dihedral angle
Benzodiazepines
X ray diffraction
Boats
Discrete Fourier transforms
Molecular structure
Conformations
Cations
X rays

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

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title = "Organometallic 1,5-benzodiazepine and 1,5-benzodiaze pinium compounds: Synthesis, characterization, X-ray diffraction structures and theoretical investigation",
abstract = "The organometallic tridentate ketoamine or enaminone compound, (η5-Cp)Fe(h5-CJH4)-C(=0)-CH= C(Me)-NH-C6H4-o-NH2, undergoes an intramolecular cyclocondensation promoted by Cu(C104) 2-6H20 (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.",
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Organometallic 1,5-benzodiazepine and 1,5-benzodiaze pinium compounds : Synthesis, characterization, X-ray diffraction structures and theoretical investigation. / Gallardo, Cristina; Trujillo, Alexander; Fuentealba, Mauricio; Vega, Andres; Carrillo, David; Manzur, Carolina.

En: Journal of the Chilean Chemical Society, Vol. 52, N.º 3, 01.01.2007, p. 1266-1270.

Resultado de la investigación: Article

TY - JOUR

T1 - Organometallic 1,5-benzodiazepine and 1,5-benzodiaze pinium compounds

T2 - Synthesis, characterization, X-ray diffraction structures and theoretical investigation

AU - Gallardo, Cristina

AU - Trujillo, Alexander

AU - Fuentealba, Mauricio

AU - Vega, Andres

AU - Carrillo, David

AU - Manzur, Carolina

PY - 2007/1/1

Y1 - 2007/1/1

N2 - The organometallic tridentate ketoamine or enaminone compound, (η5-Cp)Fe(h5-CJH4)-C(=0)-CH= C(Me)-NH-C6H4-o-NH2, undergoes an intramolecular cyclocondensation promoted by Cu(C104) 2-6H20 (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.

AB - The organometallic tridentate ketoamine or enaminone compound, (η5-Cp)Fe(h5-CJH4)-C(=0)-CH= C(Me)-NH-C6H4-o-NH2, undergoes an intramolecular cyclocondensation promoted by Cu(C104) 2-6H20 (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.

KW - DFT calculations

KW - Ferrocenyl enaminone

KW - Ferrocenyl ketoamine

KW - Organometallic diazepine

KW - Organometallic diazepinium

KW - X-ray structures

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