C–H.I− interactions in ferrocene derivatives: structures of (Ferrocenylmethyl)triphenylphosphonium iodide and 1,1'-ferrocenediylbis(methyltriphenylphosphonium iodide) dichloromethane solvate (1/1)

Glidewell, Christopher; Zakaria, Choudhury M.; Ferguson, George; Gallagher, John F.

doi:10.1107/s0108270193007929

Cited by 9 publications

(3 citation statements)

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“…In total, seven unique contacts of this type are observed, with CÁ Á ÁI distances in the range 3.655 (4)-4.075 (4) Å (Table 2). These values are similar to those of contacts described previously (Ferguson et al, 1994;Glidewell et al, 1994), although comparable examples of C-HÁ Á ÁI hydrogen bonding are relatively rare. The present system is important and demonstrates a clear discrimination of the binding sites, which follows a common pattern for convenient hydrogen bonding: the prefered acceptor is atom I3 (four contacts), which is terminal and is the most underbonded and electronegative.…”

Section: Commentsupporting

confidence: 88%

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Degtyarenko

Domasevitch

2013

Acta Crystallogr C

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New complexes containing the 1,4-bis(pyridazin-4-yl)benzene ligand, namely diaquatetrakis[1,4-bis(pyridazin-4-yl)benzene-κN(2)]cadmium(II) hexaiodidodicadmate(II), [Cd(C14H10N4)4(H2O)2][Cd2I6], (I), and poly[[μ-1,4-bis(pyridazin-4-yl)benzene-κ(2)N(2):N(2')]bis(μ-thiocyanato-κ(2)N:S)cadmium(II)], [Cd(NCS)2(C14H10N4)]n, (II), demonstrate the adaptability of the coordination geometries towards the demands of slipped π-π stacking interactions between the extended organic ligands. In (I), the discrete cationic [Cd-N = 2.408 (3) and 2.413 (3) Å] and anionic [Cd-I = 2.709 (2)-3.1201 (14) Å] entities are situated across centres of inversion. The cations associate via complementary O-H...N(2') hydrogen bonding [O...N = 2.748 (4) and 2.765 (4) Å] and extensive triple π-π stacking interactions between pairs of pyridazine and phenylene rings [centroid-centroid distances (CCD) = 3.782 (4)-4.286 (3) Å] to yield two-dimensional square nets. The [Cd2I6](2-) anions reside in channels generated by packing of successive nets. In (II), the Cd(II) cation lies on a centre of inversion and the ligand is situated across a centre of inversion. A two-dimensional coordination array is formed by crosslinking of linear [Cd(μ-NCS)2]n chains [Cd-N = 2.3004 (14) Å and Cd-S = 2.7804 (5) Å] with N(2):N(2')-bidentate organic bridges [Cd-N = 2.3893 (12) Å], which generate π-π stacks by double-slipped interactions between phenylene and pyridazine rings [CCD = 3.721 (2) Å].

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Section: Commentsupporting

confidence: 88%

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Degtyarenko

Domasevitch

2013

Acta Crystallogr C

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“…The Fe-C(Cp) bond lengths are in the range 2.0349 (12)-2.0471 (13) Å [average 2.0498 (13) Å ] with the FeÁ Á ÁCpcentroid distance being 1.6550 (6) Å . The Fe-C bond to the substituted carbon [Fe-C1 2.0349 (12)] is shorter than the remaining Fe-C bond lengths, as is seen in similar 1,1 0disubstituted ferrocene derivatives (Glidewell et al, 1994). The conformation of the ferrocenyl unit is exactly staggered by inversion symmetry, and the centrosymmetry also makes the Cp-Fe-Cp linkage linear and the Cp rings parallel.…”

Section: Structural Commentarymentioning

confidence: 91%

Synthesis and crystal structure of 1,1′-bis{[4-(pyridin-2-yl)-1,2,3-triazol-1-yl]methyl}ferrocene, and its complexation with Cu^I

et al. 2020

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The title compound, [Fe(C13H11N4)2], was synthesized starting from 1,1′-ferrocenedicarboxylic acid in a three-step reaction sequence. The dicarboxylic acid was reduced to 1,1′-ferrocenedimethanol using LiAlH4 and subsequently converted to 1,1′-bis(azidomethyl)ferrocene in the presence of NaN3. The diazide was treated with 2-ethynylpyridine under `click' conditions to give the title compound in 75% yield. The FeII center lies on an inversion center in the crystal. The two pyridyltriazole wings are oriented in an anti conformation and positioned exo from the FeII center. In the solid state, the molecules interact by C—H...N, C—H...π, and π–π interactions. The complexation of the ligand with [Cu(CH3CN)4](PF6) gives a tetranuclear dimeric complex.

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“…A preliminary effort at understanding a structure-activity relationship with three N-iodomethyl quaternary ammonium salts (I), (II) and (III) of the form [ICH 2 N(CH 3 ) 3 (CH 2 ) n CH C(Ph) 2 ] + ÁI À (with n = 2, 3 and 4, respectively) is currently being carried out. One possible approach to understand the different activities is to establish what kind of interactions are present in compounds (I)-(III), for example whether C-IÁ Á ÁI À (Desiraju et al, 2013), C-HÁ Á ÁI À (Glidewell et al, 1994), C-HÁ Á Á (Nishio et al, 1998) or cation- (Dougherty, 1996), and if so, how these interactions may affect their structure and biological properties.…”

Section: Chemical Context and Background To Halogen Bonding And Catiomentioning

confidence: 99%

Crystal structures of three newN-halomethylated quaternary ammonium salts

et al. 2015

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In the crystals of the title N-halomethylated quaternary ammonium salts, there are short I⋯I− interactions of 3.564 (4), 3.506 (1) and 3.55781) Å for compounds (I), (II) and (III), respectively. In (I), molecules are linked by C—H⋯I− and C—H⋯π interactions, together with the I⋯I− short contacts, forming ribbons along [100]. In (II), there are only C—H⋯I− interactions, which together with the I⋯I− short contacts, lead to the formation of helices along [010]. In (III), apart from the I⋯I− short contacts, there are no other significant intermolecular interactions present.

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C–H.I− interactions in ferrocene derivatives: structures of (Ferrocenylmethyl)triphenylphosphonium iodide and 1,1'-ferrocenediylbis(methyltriphenylphosphonium iodide) dichloromethane solvate (1/1)

Cited by 9 publications

References 10 publications

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Synthesis and crystal structure of 1,1′-bis{[4-(pyridin-2-yl)-1,2,3-triazol-1-yl]methyl}ferrocene, and its complexation with Cu^I

Crystal structures of three newN-halomethylated quaternary ammonium salts

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C–H.I− interactions in ferrocene derivatives: structures of (Ferrocenylmethyl)triphenylphosphonium iodide and 1,1'-ferrocenediylbis(methyltriphenylphosphonium iodide) dichloromethane solvate (1/1)

Cited by 9 publications

References 10 publications

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions

Synthesis and crystal structure of 1,1′-bis{[4-(pyridin-2-yl)-1,2,3-triazol-1-yl]methyl}ferrocene, and its complexation with CuI

Crystal structures of three newN-halomethylated quaternary ammonium salts

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Synthesis and crystal structure of 1,1′-bis{[4-(pyridin-2-yl)-1,2,3-triazol-1-yl]methyl}ferrocene, and its complexation with Cu^I