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Title: Synthesis, characterization, crystal structures and computational studies on novel cyrhetrenyl hydrazones
Author: Gómez, Johana
Leiva, Nelson
Arancibia, Rodrigo
Oyarzo, Juan
Buono-Cuore, Gonzalo E.
Klahn, Hugo
Artigas, Vania
Fuentealba, Mauricio
Bosque Pueyo, Ramón
Aullón López, Gabriel
López Martínez, Ma. Concepción
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Keywords: Estructura cristal·lina (Sòlids)
Compostos orgànics
Layer structure (Solids)
Organic compounds
Issue Date: 18-Jun-2016
Publisher: Elsevier B.V.
Abstract: The synthesis of novel cyrhetrenyl hydrazones of general formula [Re{(η5-C5H4)single bondC(R1) = NNHR2}(CO)3] {with R1 = H and R2 = 4-NO2single bondC6H4 (4a), C6H5 (4b) or H (4c) or R1 = Me and R2 = 4-NO2single bondC6H4 (5a), C6H5 (5b) or H (5c)} is described. Compounds 4a-4c and 5a-5c were characterized by mass spectrometry and IR spectroscopy. 1H and 13C{1H} NMR studies revealed that 4a-4c and 5a-5c adopt the anti-(E) configuration in solution. X-ray crystal structures of compounds 4a and 5c confirmed the trans-arrangement of the cyrhetrenyl 'Re(η5-C5H4)(CO)3' and the -NHR2 moieties and the existence of strong hydrogen bonds involving the single bondNHsingle bond unit. Molecular Orbital calculations at a DFT level have also been carried out in order to rationalize the influence of the nature of the substituent R3 of [R3CH = NNH(4-NO2single bondC6H4)] (R3 = ferrocenyl, (3a), cyrhetrenyl (4a), phenyl (6a) or cymantrenyl (7a) on the electronic delocalization, the nucleophilicity of the imine carbon, the polarizability and hyperpolarizability of these compounds, and computational studies using time-dependent density functional (TD-DFT) calculations have also been carried out in order to assign the bands detected in their electronic spectra and to explain the effect produced by the solvent.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organometallic Chemistry, 2016, vol. 819, p. 129-137
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ISSN: 0022-328X
Appears in Collections:Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

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