Activation of σ(C–H) bonds of [Fe{(η5-C5H4)–C(Me)N–NC(H)(C6H3–2,6-R)}2] (with R=Cl or H) promoted by palladium(II)

López, Concepción; Bosque, Ramón; Arias, Javier; Evangelio, Emilia; Soláns, Xavier; Font-Bardı́a, Mercè

doi:10.1016/s0022-328x(03)00137-2

Cited by 15 publications

(13 citation statements)

References 40 publications

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“…In 2b (Fig. 2), the ferrocenyl fragment has an eclipsed conformation similar to that found in other monosubstituted ferrocenyl derivatives [4a, 5,9].…”

Section: -supporting

confidence: 77%

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Gómez

Klahn

Fuentealba

et al. 2015

Inorganic Chemistry Communications

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“…In 2b (Fig. 2), the ferrocenyl fragment has an eclipsed conformation similar to that found in other monosubstituted ferrocenyl derivatives [4a, 5,9].…”

Section: -supporting

confidence: 77%

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Gómez

Klahn

Fuentealba

et al. 2015

Inorganic Chemistry Communications

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“…Their MS spectra showed peaks due to the molecular cations [M] + and those arising from the successive dissociation of the remaining CO ligands. IR spectra of 4a-4c and 5a-5c in CH 2 Cl 2 showed the following common features: a) two intense bands at 2023 and 1929 cm -1 , that are characteristic of the asymmetric (ν as ) and symmetric (ν s ) stretchings of the terminal CO ligands of cyrhetrene derivatives [9a, 14,15], and b) an intense and sharp absorption (at around 1600 cm -1 ) in the same range as observed for ferrocenyl hydrazones [Fe(η 5 -C 5 H 5 ){(η 5 -C 5 H 4 )-C(R 1 )=N-NHR 2 ] with R 1 = H (1) or Me (2) [10][11][12], that has been assigned to the stretching of the functional >C=N-.…”

Section: Accepted Manuscriptmentioning

confidence: 94%

“…For instance, ferrocenylimines [5,6], oximes [7], azines and azoderivatives [8], thiosemicarbazones [9] or, to a lesser extent, monohydrazones [Fe(η 5 -C 5 H 5 ){(η 5 -C 5 H 4 )-C(R 1 )=N-NHR 2 ] (R 1 = H (1) or Me (2), Fig. 1) or the 1,1-dihydrazones (3) [10,11], are valuable as ligands in coordination and organometallic chemistry (i.e. to achieve cyclometallated compounds) [5,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, crystal structures and computational studies on novel cyrhetrenyl hydrazones

Gómez

Leiva

Arancibia

et al. 2016

Journal of Organometallic Chemistry

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A b s t r a c t:The synthesis of novel cyrhetrenyl hydrazones of general formula [Re{(η 5 -C 5 H 4 )-C(R 1 )=NNHR 2 }(CO) 3 ] {with R 1 = H and R 2 = 4-NO 2 -C 6 H 4 (4a), C 6 H 5 (4b) or H (4c) or R 1 = Me and R 2 = 4-NO 2 -C 6 H 4 (5a), C 6 H 5 (5b) or H (5c)} is described. Compounds 4a-4c and 5a-5c were characterized by mass spectrometry and IR spectroscopy. 1 H and 13 C{ 1 H} 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(η 5 -C 5 H 4 )(CO) 3 " and the -NHR 2 moieties and the existence of strong hydrogen bonds involving the -NH-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 R 3 of [R 3 CH=NNH(4-NO 2 -C 6 H 4 )] (R 3 = ferrocenyl, (3a), cyrhetrenyl (4a) and phenyl (6a) 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.

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“…Several studies on the Schiff base containing-ferrocene have been reported recently [2][3][4][5][6]. The title molecule is in a trans configuration of the benzene ring and the cyclopentadienyl ring in respect to the N=C11 bond; the dihedral angle between the planes C6-C10 and N/C13-C18 is 45(1)°.Inthe ferrocen group, the Fe-Cbond lengths are within the normal range [7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of [2-(diphenylphosphino)phenyliminoethyl]- ferrocene, Fe(C₅H₅)(C₂₅H₂₁NP)

Kuang¹,

Fang²,

Liu³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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C 30 H 26 FeNP, monoclinic, P2 1 /n (no. 14), a =10.750(2) Å, b =9.077(2) Å, c =24.489(5) Å, b =90.85(3)°, V =2389.3 Å 3 , Z =4,R gt(F) =0.042, wRref(F 2 ) =0.113, T =293 K. Source of materialThe raw material 2-(diphenylphosphino)aniline was prepared by al iterature method [1], and acetylferrocene was commercially obtained. Acetylferrocene (1.14 g, 5.0 mmol), 5 Å molecular sieve (2.0 g) and 2-(diphenylphosphino)aniline (1.325 g, 5.0 . mmol) were suspended in dried toluene (20 cm 3 ). The reaction mixtures were refluxed at stirring for 5-6day. In order to control the progress of the condensation reaction the infrared spectra of the solutions were recorded. Daily addition of small quantities of the amine (0.2 g, 1mmol) and molecular sieve (4 Å) was needed to force the displacement of the equilibria. This procedure was repeated for 5-6day until the infrared spectra of the samples did not exhibit the band due to the asymmetrical stretching of the C=O group of the acetylferrocene [n(C=O) 1662 cm -1 ]. Then, the molecular sieves were removed by vacuum filtration and washed with ether until the liquid became colourless. The orange-red solution was concentrated on arotary evaporator, and the oil formed was treated with methylene dichloride (10 cm 3 ). Slow evaporation of the solvent afforded the red crystal of the title compound (1.950 g, yield 81 %). DiscussionFerrocene and its derivatives have attracted much attention for their potential applications as molecular sensors, magnetic and optical materials, and in homogeneous catalysis. Several studies on the Schiff base containing-ferrocene have been reported recently [2][3][4][5][6]. The title molecule is in a trans configuration of the benzene ring and the cyclopentadienyl ring in respect to the N=C11 bond; the dihedral angle between the planes C6-C10 and N/C13-C18 is 45(1)°.Inthe ferrocen group, the Fe-Cbond lengths are within the normal range [7]. The Fe1···Cg1 and Fe1···Cg2 distances are 1.629 Å and 1.634 Å,respectively, and the Cg1···Fe···Cg2 angle is 178.9°,where Cg1 and Cg2 are the centroids of the substituted and unsubstituted Cp rings, respectively. The two Cp rings are almost eclipsed, with adihedral angle of 1.4°,and the largest torsion angle C2···Cg1···Cg2···C9 is 6.1°.Inthe triphenylphosphine group, the Pa tom adopts as lightly distorted pyramidal coordination.

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Activation of σ(C–H) bonds of [Fe{(η5-C5H4)–C(Me)N–NC(H)(C6H3–2,6-R)}2] (with R=Cl or H) promoted by palladium(II)

Cited by 15 publications

References 40 publications

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Synthesis, characterization, crystal structures and computational studies on novel cyrhetrenyl hydrazones

Crystal structure of [2-(diphenylphosphino)phenyliminoethyl]- ferrocene, Fe(C₅H₅)(C₂₅H₂₁NP)

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Activation of σ(C–H) bonds of [Fe{(η5-C5H4)–C(Me)N–NC(H)(C6H3–2,6-R)}2] (with R=Cl or H) promoted by palladium(II)

Cited by 15 publications

References 40 publications

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Unsymmetrical cyrhetrenyl and ferrocenyl azines derived from 5-nitrofurane: Synthesis, structural characterization and electrochemistry

Synthesis, characterization, crystal structures and computational studies on novel cyrhetrenyl hydrazones

Crystal structure of [2-(diphenylphosphino)phenyliminoethyl]- ferrocene, Fe(C5H5)(C25H21NP)

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Crystal structure of [2-(diphenylphosphino)phenyliminoethyl]- ferrocene, Fe(C₅H₅)(C₂₅H₂₁NP)