The binuclear trimethyl/triethylantimony(V) bis-catecholate derivatives of four-electron reduced 4,4′-di-(3-methyl-6-tert-butyl-o-benzoquinone)

Poddel’sky, Andrey I.; Сомов, Н. В.; Druzhkov, N. O.; Cherkasov, V. K.; Abakumov, G. A.

doi:10.1016/j.jorganchem.2010.09.008

Cited by 18 publications

(3 citation statements)

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“…This is also valid for the antimony o quinone complexes. Among the binuclear antimony complexes (bis(catecholate) derivatives), the derivatives of 4,4' di [(3 methyl 6 tert butyl o benzoquinone) and di o quinones based on 3,6 di tert butyl o benzoquinone containing the ethylene or piperazine bridging groups were described [27][28][29][30].The purpose of the present work is to synthesize antimony(V) bis(catecholate) complexes based on nonsymmetric 1,1' spirobis[3,3 dimethylindane quinone 5,6] (Q Spiro Q) and to study them by IR and NMR spectroscopy and cyclic voltammetry (CV). …”

mentioning

confidence: 99%

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

et al. 2012

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Scientific interest in coordination and organome tallic antimony(V) derivatives is continuously increas ing in the recent two decades [1][2][3][4], which is due to the possibility of using these compounds in diverse areas of fundamental and applied science. These com plexes demonstrate structural variety from monomeric compounds to associated structures and supramolecu lar ensembles [5][6][7][8][9][10]. The antimony compounds are used as components of catalytic systems and reagents in fine organic and organometallic synthesis [11][12][13][14]. In addition, many organoantimony compounds dem onstrate antimicrobial properties and possess antitu mor activity [15][16][17].The chemistry of coordination compounds of o quinone and related ligands is widely developed to the present time [18][19][20] because of the use of their com plexes as model objects in magnetochemical studies, for the construction of molecular switchers, and as catalytic systems. Sterically hindered di o quinones are presently studied to a less extent, although they represent a promising type of ligands for the design of spatially ordered structures [21][22][23][24][25]. The introduction of various binding units (bridging groups) into the di o quinone structure makes it possible to change con siderably the character of mutual effects of the o quinone moieties in the di o quinone molecule and to vary the exchange magnetic interactions between the radical anion semiquinone derivatives from antiferro magnetic to ferromagnetic [22,24].In addition, the most part of studies of the o quinone complexes was carried out with the transi tion metal compounds, whereas the coordination chemistry of nontransition metals with redox active ligands is poorly studied [26]. This is also valid for the antimony o quinone complexes. Among the binuclear antimony complexes (bis(catecholate) derivatives), the derivatives of 4,4' di [(3 methyl 6 tert butyl o benzoquinone) and di o quinones based on 3,6 di tert butyl o benzoquinone containing the ethylene or piperazine bridging groups were described [27][28][29][30].The purpose of the present work is to synthesize antimony(V) bis(catecholate) complexes based on nonsymmetric 1,1' spirobis[3,3 dimethylindane quinone 5,6] (Q Spiro Q) and to study them by IR and NMR spectroscopy and cyclic voltammetry (CV). EXPERIMENTALThe synthesis and study of the properties of the complexes were carried out in evacuated ampules in the absence of oxygen. In all cases, the yields of the target products were higher than 90%. The solvents Triaryl and Trialkylantimony(V) Bis(catecholates) Based on 1,1' Spirobis[3,3 Dimethylindanequinone 5,6]: Abstract-A series of new binuclear bis(catecholate) antimony(V) complexes based on 1,1' spirobis[3,3 dimethylindanequinone 5,6] with various substituents at the central antimony atoms, R 3 Sb(Cat Spiro Cat)SbR 3 (I-IV) and R 3 Sb(Cat Br Spiro Br Cat)SbR 3 (V-VIII) (R = p fluorophenyl, phenyl, p tolyl, and ethyl), were synthesized. Spirobis(catecholates) I-III exhibit two one electron oxidation waves on the cycli...

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confidence: 99%

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

et al. 2012

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“…The six-membered carbon ring C(1-6) is aromatic, with average C-C bond distances of 1.400 ± 0.015 Å, which is very close to the same value for catechol L 1 . In general, the geometrical characteristics of the redox-active catecholato ligand in 1 are typical for various antimony(V) catecholates [69][70][71][72][73][74][75][76][77][78][79].…”

Section: Electrochemistrymentioning

confidence: 99%

Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

et al. 2020

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New polyfunctional sterically hindered 3,5-di-tert-butylcatechols with an additional phenolic group in the sixth position connected by a bridging sulfur atom—(6-(CH2-S-tBu2Phenol)-3,5-DBCat)H2 (L1), (6-(S-tBu2Phenol)-3,5-DBCat)H2 (L2), and (6-(S-Phenol)-3,5-DBCat)H2 (L3) (3,5-DBCat is dianion 3,5-di-tert-butylcatecolate)—were synthesized and characterized in detail. The exchange reaction between catechols L1 and L3 with triphenylantimony(V) dibromide in the presence of triethylamine leads to the corresponding triphenylantimony(V) catecholates (6-(CH2-S-tBu2Phenol)-3,5-DBCat)SbPh3 (1) and (6-(S-Phenol)-3,5-DBCat)SbPh3 (2). The electrochemical properties of catechols L1–L3 and catecholates 1 and 2 were investigated using cyclic voltammetry. The electrochemical oxidation of L1–L3 at the first stage proceeds with the formation of the corresponding o-benzoquinones. The second process is the oxidation of the phenolic moiety. Complexes 1 and 2 significantly expand their redox capabilities, owing to the fact that they can act as the electron donors due to the catecholate metallocycle capable of sequential oxidations, and as donors of the hydrogen atoms, thus forming a stable phenoxyl radical. The molecular structures of the free ligand L1 and complex 1 in the crystal state were determined by single-crystal X-ray analysis.

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“…Both thio-and selenosemicarbazone groups have been shown to be effective ligands for indium, antimony and bismuth complexes, 133 NCN pincer ligands may be used to support Sb-and Bi-based phosphate groups 134 and, for bismuth, novel OCO pincer compounds such as 79 have been described. 135 For antimony, the catecholates 80, formed by reaction of the corresponding quinone with an alkylstibine 136 and the ability of related compounds to act as radical scavengers has also been reported. 137 It was concluded that the activity of the compounds was dependant on the first oxidation potential.…”

Section: Arsenic Antimony and Bismuthmentioning

confidence: 99%

Nitrogen, phosphorus, arsenic, antimony and bismuth

Lynam¹

2012

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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The binuclear trimethyl/triethylantimony(V) bis-catecholate derivatives of four-electron reduced 4,4′-di-(3-methyl-6-tert-butyl-o-benzoquinone)

Cited by 18 publications

References 28 publications

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

Triaryl- and trialkylantimony(V) Bis(catecholates) based on 1,1′-spirobis[3,3-dimethylindanequinone-5,6]: Spectroscopic and electrochemical studies

Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

Nitrogen, phosphorus, arsenic, antimony and bismuth

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