A zwitterionic complex: crystal and molecular structure of trichloro(N-(4'-pyridyl)-4-ethoxypyridinium)zinc(II)

Steffen, William L.; Palenik, Gus J.

doi:10.1021/ic50183a048

Cited by 19 publications

(2 citation statements)

References 24 publications

(7 reference statements)

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“…A recent publication (James et al, 2001) describes the roomtemperature structural characterization of 4-piperidinylpyridinium tetrachloroferrate(III), which was undertaken in order to understand better the low-temperature magnetic ordering arising from the particular spatial distribution of the magnetic centres within the lattice. The results brie¯y drew attention to other features of interest peripheral to that objective, concerning the nature of the cation in which the inter-ring bond appeared to exhibit a high bond order not evident, for example, in the N-(4 H -pyridyl)-4-ethoxypyridinium species coordinated to trichlorozincate(II) (Steffen & Palenik, 1978). As there appears to be no other structural characterization of the 4-piperidinylpyridinium species or close relatives in the literature, we considered it to be of interest to execute a further study under conditions conducive to providing a description of greater precision, i.e.…”

Section: Commentmentioning

confidence: 99%

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

James

Mutrofin

Skelton³

et al. 2003

Acta Crystallogr C

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Structural characterization of the title compound, C(10)H(15)N(2)(+).PF(6)(-), shows it to be ionic, with the pyridine rather than the piperidine N atom being protonated and forming hydrogen bonds to the counter-ions, resulting in two independent ion pairs. A number of unusual features are noted, in particular the remarkably close inter-ring hydrogen contacts [1.97 (3)-2.00 (3) A] and the considerable differences in the pair of cations, in respect of the torsion angles within the piperidine ring involving the bonds to either side of the N atom.

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Section: Commentmentioning

confidence: 99%

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

James

Mutrofin

Skelton³

et al. 2003

Acta Crystallogr C

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“…Zwitterionic complexes of Co 2÷ are already known, and for related literature the interested reader is referred to the following: Kolodny et al (1973), Vallarino et al (1973, Steffen & Palenik (1978), Gerloch & Manning (1981) and Bruni et al (1991).…”

Section: A Few Of Them Show Some Antitumour Activity Such As the Bmentioning

confidence: 99%

Cobalt(II) complexes of piperazine and derivatives: 1-methylpiperazin-4-ium trichloro(1-methylpiperazine-N⁴)cobaltate(II)

Marzotto¹,

Clemente²,

Valle³

1999

Acta Crystallogr C

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Tunable N‐substitution in Zwitterionic Benzoquinonemonoimine Derivatives: Metal Coordination, Tandemlike Synthesis of Zwitterionic Metal Complexes, and Supramolecular Structures

Yang

Siri

Braunstein

2005

Chemistry A European J

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Full details on a very efficient transamination reaction for the synthesis of zwitterionic N,N-dialkyl-2-amino-5-alcoholate-1,4-benzoquinonemonoiminium derivatives [C6H2(=NHR)2(=O)2] 5-16 are reported. The molecular structures of zwitterions 5 (R=CH3) in 5.H2O, 13 (R=CH2CH2OMe), 15 (R=CH2CH2NMe2), and of the parent, unsubstituted system [C6H2(=NH2)2(=O)2] 4 in 4.H2O have been established by single-crystal X-ray diffraction. This one-pot preparation can be carried out in water, MeOH, or EtOH and allows access to new zwitterions with N-substituents bearing functionalities such as -OMe (13), -OH (9-12), NR1R2 with R1 = or not equal R2 (14-16) or an alkene (8), leading to a rich coordination chemistry and allowing fine-tuning of the supramolecular arrangements in the solid state. As previously described for 15, which reacted with Zn(acac)2 to afford the octahedral Zn(II) complex [Zn[C6H2(NCH2CH2NMe2)O(O)(NHCH2CH2NMe2)]2] (20), ligands 13 and 16 with coordinating "arms" afforded with Zn(acac)2 the 2:1 adducts [Zn[C6H2(NCH2CH2X)O(=O)(NHCH2CH2NX)]2] 19 (X=OMe) and 21 (X=NHEt), with N2O4 and N4O2 donor sets around the octahedral Zn(II) center, respectively. Furthermore, zwitterions 15 and 16 reacted with ZnCl2 to give the stable, crystallographically characterized Zn(II) zwitterionic complexes [ZnCl2[C6H2(NCH2CH2NR1R2)O(=O)(NHCH2CH2NHR1R2)]] 22 (R1=R2=Me) and 23 (R1=Et, R2=H) by means of an unprecedented, tandemlike synthesis in which 1) the two pendant amino groups of the organic benzoquinonemonoimine zwitterionic precursor favor metal coordination and proton transfer and 2) the saturated linker prevents pi-conjugation between the charges. The nature of the structural arrangements in the solid state for both inorganic (20, 22, 23) and organic (5, 9, 13, and 15) molecules is determined by subtle variations in the nature of the N-substituent on the zwitterion precursor.

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A zwitterionic complex: crystal and molecular structure of trichloro(N-(4'-pyridyl)-4-ethoxypyridinium)zinc(II)

Cited by 19 publications

References 24 publications

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

Cobalt(II) complexes of piperazine and derivatives: 1-methylpiperazin-4-ium trichloro(1-methylpiperazine-N⁴)cobaltate(II)

Tunable N‐substitution in Zwitterionic Benzoquinonemonoimine Derivatives: Metal Coordination, Tandemlike Synthesis of Zwitterionic Metal Complexes, and Supramolecular Structures

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A zwitterionic complex: crystal and molecular structure of trichloro(N-(4'-pyridyl)-4-ethoxypyridinium)zinc(II)

Cited by 19 publications

References 24 publications

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

4-(Piperidin-1-yl)pyridinium hexafluorophosphate at 150 K

Cobalt(II) complexes of piperazine and derivatives: 1-methylpiperazin-4-ium trichloro(1-methylpiperazine-N4)cobaltate(II)

Tunable N‐substitution in Zwitterionic Benzoquinonemonoimine Derivatives: Metal Coordination, Tandemlike Synthesis of Zwitterionic Metal Complexes, and Supramolecular Structures

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Cobalt(II) complexes of piperazine and derivatives: 1-methylpiperazin-4-ium trichloro(1-methylpiperazine-N⁴)cobaltate(II)