Synthesis and Structural Studies of Pyridine-2-selenolates − Reactions with Electrophilic Phosphorus(III) Compounds and Related Complex Chemistry

Laube, Jörg; Jäger, Stefan; Thöne, Carsten

doi:10.1002/1099-0682(200108)2001:8<1983::aid-ejic1983>3.0.co;2-w

Cited by 35 publications

(20 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[16] 3-Hydroxypyridine-2(1H)-selone (10) was prepared in 1986 by Smith and co-workers and formulated as a selone mainly by analogy with the structural assignment of the corresponding sulfur compound. [17] More recently, Thçne and co-workers [18] could isolate both compounds 8 and 9 from the same reaction mixture. An X-ray structure analysis of 8 ( 77 Se NMR chemical shift at d = 314 ppm in CDCl 3 and d = 215 ppm in H 2 O) confirmed its selone structure.…”

Section: Results and Discussion Synthesismentioning

confidence: 99%

Pyridoxine‐Derived Organoselenium Compounds with Glutathione Peroxidase‐Like and Chain‐Breaking Antioxidant Activity

Singh

Poon

Butcher

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

One of the vitamin B6 vitamers, pyridoxine, was modified to incorporate selenium in various oxidation states in place of the methyl group in position 2. Such compounds were conveniently accessed by treatment of bis-4,5-(carboethoxy)-2-iodo-3-pyridinol with disodium diselenide and LiAlH4 -reduction. After work-up, selone 7 was isolated in good yield as an air-stable crystalline material. Hydrogen bonding to the neighboring hydroxyl group, as revealed by the short intramolecular Se⋅⋅⋅H distance in the crystal structure is likely to provide extra stabilization to the compound. Computational studies showed that selone 7 is more stable than the corresponding selenol tautomer by 12.2 kcal mol(-1) . Hydrogen peroxide oxidation of the selone 7 afforded diselenide 12, and, on further oxidation, seleninic acid 13. Treatment of the seleninic acid with thiophenol provided an isolable selenosulfide 14. The glutathione peroxidase-like properties of the pyridoxine-derived compounds were assessed by using the coupled reductase method. Seleninic acid 13 was found to be twofold more active than ebselen. The chain-breaking capacity of the pyridoxine compounds were studied in a water/chlorobenzene membrane model containing linoleic acid as an oxidizable substrate and N-acetylcysteine as a thiol reducing agent. Diselenide 15 could match α-tocopherol when it comes to reactivity towards peroxyl radicals and inhibition time.

show abstract

Section: Results and Discussion Synthesismentioning

confidence: 99%

Pyridoxine‐Derived Organoselenium Compounds with Glutathione Peroxidase‐Like and Chain‐Breaking Antioxidant Activity

Singh

Poon

Butcher

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The tilt angles α showed values of 3.9(1)° at Fe1 and 5.8(1)° at Fe2 for both ferrocene units and indicated that almost no ring strain was present. The Au-P contacts between 2.305(10) Å and 2.337(9) Å were slightly longer than those observed in 7 but in the typical range for P-Au bond lengths [ 24 , 25 ]. For the solid-state structures of compounds 7 and 8 , no inter- or intramolecular Au···Au interactions were observed (Au···Au > 6.7 Å in 8 ).…”

Section: Resultsmentioning

confidence: 80%

C2-Symmetric P-Stereogenic Ferrocene Ligands with Heavier Chalcogenophosphinous Acid Ester Donor Sites

2021

View full text Add to dashboard Cite

tert-Butyl-substituted diphospha[2]ferrocenophane was used as a stereochemically confined diphosphane to investigate the addition of various dichalcoganes (R2Ch2; Ch = S, Se, Te and R = Me, Ph). Bischalcogenophosphinous acid esters bearing four soft donor sides were obtained as a mixture of rac and meso diastereomers and characterized by means of multinuclear NMR and X-ray analysis. The coordination chemistry of multidentate ligand 3b was explored toward d10 coinage metal centers (Cu(I), Ag(I), and Au(I)), yielding various bimetallic complexes.

show abstract

“…A solution of [κ 3 -Tpsem]ZnSH (6 mg, 0.01 mmol) in CH 2 Cl 2 (ca. 0.5 mL) was allowed to evaporate slowly at room temperature, thereby depositing orange crystals of {[κ 3 -Tpsem]Zn} 2 (µ-S) suitable for X-ray diffraction (2 mg, 31%…”

Section: Synthesis Of {[κ 3 -Tpsem]zn} 2 (µ-S)mentioning

confidence: 99%

“…Molecular structure of {[κ 3 -Tpsem]Zn} 2 S.Interconversion of [κ 3 -Tpsem]ZnSH and {[κ 3 -Tpsem]Zn} 2 (µ-S)A mixture composed of {[κ3 -Tpsem]Zn} 2 (µ-S) and [κ 3 -Tpsem]ZnSH (2.5:1, ca. 5 mg) was dissolved in CD 2 Cl 2 in an NMR tube equipped with J.…”

mentioning

confidence: 99%

The Synthesis and Structures of Tris(2-pyridylseleno)methyl Zinc Compounds with κ2-, κ3-, and κ4-Coordination Modes

Rong

Parkin

2013

Aust. J. Chem.

View full text Add to dashboard Cite

Tris(2-pyridylseleno)methane, [Tpsem]H, has been employed to synthesize the bis(trimethylsilyl)amido zinc complex [κ3-Tpsem]ZnN(SiMe3)2. The latter compound provides access to a variety of other [Tpsem]ZnX derivatives, which include the isocyanate complex [κ4-Tpsem]ZnNCO, the hydrosulfido complex [κ3-Tpsem]ZnSH, the sulfido complex {[κ3-Tpsem]Zn}2(μ-S), the 2 : 1 complex [κ2-Tpsem]2Zn and the pyridyl-2-selenolate complex [κ4-Tpsem]Zn-(κ2-SeC6H4N), thereby demonstrating that the [Tpsem] ligand can exhibit κ2-, κ3-, and κ4-coordination modes. Variable-temperature 1H NMR spectroscopic studies demonstrate that [κ3-Tpsem]ZnN(SiMe3)2, [κ3-Tpsem]ZnSH, and {[κ3-Tpsem]Zn}2(μ-S) are fluxional on the NMR timescale.

show abstract

Synthesis and Structural Studies of Pyridine-2-selenolates − Reactions with Electrophilic Phosphorus(III) Compounds and Related Complex Chemistry

Cited by 35 publications

References 47 publications

Pyridoxine‐Derived Organoselenium Compounds with Glutathione Peroxidase‐Like and Chain‐Breaking Antioxidant Activity

Pyridoxine‐Derived Organoselenium Compounds with Glutathione Peroxidase‐Like and Chain‐Breaking Antioxidant Activity

C2-Symmetric P-Stereogenic Ferrocene Ligands with Heavier Chalcogenophosphinous Acid Ester Donor Sites

The Synthesis and Structures of Tris(2-pyridylseleno)methyl Zinc Compounds with κ2-, κ3-, and κ4-Coordination Modes

Contact Info

Product

Resources

About