Tetrahydropoxen: 2,2′-(1,2-ethanediylbis(iminomethylene)) bis(pyridine N-oxide) and its complexes. X-ray structure of [Cu(H4-poxen)H2O](ClO4)2·H2O and [Co(poxen)H2O](ClO4)2

Boča, Roman; Nemeĉková, Monika; Vrbová, Martina; Baran, Peter; Svoboda, Ingrid; Fueß, H.

doi:10.1016/s0277-5387(00)00324-7

Polyhedron

2000

DOI: 10.1016/s0277-5387(00)00324-7

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Tetrahydropoxen: 2,2′-(1,2-ethanediylbis(iminomethylene)) bis(pyridine N-oxide) and its complexes. X-ray structure of [Cu(H4-poxen)H2O](ClO4)2·H2O and [Co(poxen)H2O](ClO4)2

Roman Boča

Monika Nemeĉková

Martina Vrbová

et al.

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Cited by 4 publications

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“…The coordination bond distances d(Cu-O) =1 .955 Å( av.) fort he mspo ligand are comparable with those described in the literature [7,8] [3,9]. Theangle ÐCu-O-N =120.4°(av.)…”

supporting

confidence: 85%

Crystal structure of diaquatetrakis[μ-2,2′-(methylene-bis(sulfanediyl))bis(pyridine 1-oxide)dicopper(II) dibromide diperchlorate, [Cu2(H2O)2(C11H11N2O2S2)4]Br2(ClO4)2

Niu¹,

Lin²,

Shan³

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 2,2'-(Methylene-bis(sulfanediyl))bis(pyridine 1-oxide) (mspo) and copper salts thereof were prepared, comprising the following steps: oxidizing a2-acetylaminopyridine with hydrogen peroxide in an inert solvent to give a2-acetamido-pyridine 1-oxide, cleaving the acetyl group with mineral acid to give a2-aminopyridine 1-oxide, diazotizing the 2-aminopyridine 1-oxide and treating the diazonium salt with hydrochloric acid to give a2-chloropridine 1-oxide, treating the 2-chloropridine 1-oxide with asulfhydryl-donor to give a2-mercaptopyridine 1-oxide, treating the latter with a CH 2 Br 2 to give a2,2'-(methylenebis(sulfanediyl))bis(pyridine 1-oxide). Asolution of CuBr 2 (223 mg, 1m mol) in water (5 mL) was dropped slowly into asolution of mspo (532 mg, 2mmol) in EtOH (20 mL) and the pH was adjusted to 7-8 with HClO 4 .The mixed solution was stirred for 2hat80°Cand was then cooled to room temperature to give brown-yellow microcrystals, which were collectedbyfiltration, washed successivelywithH 2 Oand EtOH,and driedinvacuo.Brown-yellowsquare crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate from N,N-dimethylformamide and alcohol (1:1). Experimental detailsThe non-hydrogen atomsw ere refined anisotropically, and hydrogen atomswere added according to theoretical models. In the crystal structure, O5 and O5',O6and O6',Br1 and Br1' are disordered with occupancies of 0.86:0.14, 0.86:0.14, and 0.36:0.14, respectively. It is very difficult to locate the hydrogen atomsofcoordinated water molecules, so their information is not provided. DiscussionThe practical interest in heteroaromatic N-oxides is caused first of all by the fact that many of them show biological activity and extraction properties [1,2].Among N-oxides, there are substances possessing carcinogenic, cancerostatic, mutagenic, insecticidal, herbicidal,fungicidal, anticonvulsant,analgesic andplantgrowingp roperties. Both biological activity ande xtractional properties areconnected with complexation of N-oxide. We have been interested in the study of metal complexes of 2-mercaptopyridine 1-oxide (Hmpo) due to the fact that these complexes have been successfully used as bactericidaland antifungal agents [3][4][5]. The Cu(II) complex is adinuclear cage compound. Each Cu(II) coordination sphere is formed by four mspo ligands and one 96 Z. Kristallogr.

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“…The coordination bond distances d(Cu-O) =1 .955 Å( av.) fort he mspo ligand are comparable with those described in the literature [7,8] [3,9]. Theangle ÐCu-O-N =120.4°(av.)…”

supporting

confidence: 85%

Crystal structure of diaquatetrakis[μ-2,2′-(methylene-bis(sulfanediyl))bis(pyridine 1-oxide)dicopper(II) dibromide diperchlorate, [Cu2(H2O)2(C11H11N2O2S2)4]Br2(ClO4)2

Niu¹,

Lin²,

Shan³

2012

Zeitschrift Für Kristallographie - New Crystal Structures

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Chelate [2‐(Iminoethyl)pyridine N‐oxide]metal Complexes – Synthesis and Structural Comparison with Their Chemically Related 2‐(Iminoethyl)pyridine‐Derived Systems

et al. 2006

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The N,O‐chelate ligands 2‐(iminoethyl)pyridine N‐oxide (2a) and 2‐(iminoethyl)‐6‐isopropylpyridine N‐oxide (2b) were prepared by conventional synthetic routes, the latter involving a variant of the Reissert–Henze reaction. Treatment of 2a with FeCl2 resulted in a deoxygenation reaction of the ligand and formation of the salt [bis{2‐(iminoethyl)pyridine}FeCl]+[FeCl4]– (18a). In contrast, the reaction of 2a with PdCl2 or CoCl2 cleanly furnished the six‐membered chelate [κN,O‐2(iminoethyl)pyridine N‐oxide]MCl2 complexes (19a, M = Pd) or (20a, M = Co), respectively, which were both characterised by X‐ray diffraction. Treatment of 2b with [NiBr2(dme)], followed by crystallisation from THF, gave the complex [(κN,O‐2b)NiBr2(THF)] (21b), which features a distorted trigonal‐bipyramidal coordination geometry of the central metal atom. The reaction of 2a with [NiBr2(dme)] gave the structurally related complex [(κN,O‐2a)NiBr2(κO‐2a)] (21a). The N,O‐chelate Pd complex 19a was shown to be an active catalyst for the Suzuki coupling reaction. The ligand systems 2a,b and their related 2‐(iminoethyl)pyridines 3a,b and a variety of metal complexes of ligands 3 were also prepared and characterised for comparison by X‐ray diffraction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Hydrogen bonds dependent assembly of two novel 1D complexes constructed by bis(4-pyridinecarboxamide)alkanes-N,N′-dioxide

Cao

Sun

2012

Inorganic Chemistry Communications

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Tetrahydropoxen: 2,2′-(1,2-ethanediylbis(iminomethylene)) bis(pyridine N-oxide) and its complexes. X-ray structure of [Cu(H4-poxen)H2O](ClO4)2·H2O and [Co(poxen)H2O](ClO4)2

Cited by 4 publications

References 11 publications

Crystal structure of diaquatetrakis[μ-2,2′-(methylene-bis(sulfanediyl))bis(pyridine 1-oxide)dicopper(II) dibromide diperchlorate, [Cu2(H2O)2(C11H11N2O2S2)4]Br2(ClO4)2

Crystal structure of diaquatetrakis[μ-2,2′-(methylene-bis(sulfanediyl))bis(pyridine 1-oxide)dicopper(II) dibromide diperchlorate, [Cu2(H2O)2(C11H11N2O2S2)4]Br2(ClO4)2

Chelate [2‐(Iminoethyl)pyridine N‐oxide]metal Complexes – Synthesis and Structural Comparison with Their Chemically Related 2‐(Iminoethyl)pyridine‐Derived Systems

Hydrogen bonds dependent assembly of two novel 1D complexes constructed by bis(4-pyridinecarboxamide)alkanes-N,N′-dioxide

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