New square-pyramidal organoantimony(V) compounds; crystal structures of (biphenyl-2,2′-diyl)phenylantimony(V) dibromide, dichloride and diisothiocyanate, Sb(2,2′-C12H8)PhX2 (X = Br, Cl or NCS), and of octahedral SbPh(o-O2C6Cl4)Cl2 ·OEt2

Gibbons, Martin N.; Begley, Michael J.; Blake, Alexander J.; Sowerby, D. Bryan

doi:10.1039/a701591g

Cited by 26 publications

(5 citation statements)

References 30 publications

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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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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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“…Holmes et al [2] used the oxidative addition reaction of tetrachloro-o-benzoquinone with the corresponding stibole to form Ph 3 Sb(o-O 2 C 6 Cl 4 ) and PhSb(o-O 2 C 6 Cl 4 )(C 12 H 8 )AE0.25C 6 H 6 AE0.25CH 2 Cl 2 . Later, Gibbons et al [6] carried out the oxidative addition reaction between SbPhCl 2 and tetrachloro-o-benzoquinone in an ether solution, yielding six-coordinate tetrachlorocatechol species PhSb(o-O 2 C 6 Cl 4 )Cl 2 AEEt 2 O. This paper focuses on synthesizing novel triphenylantimony complexes with some o-benzoquinones and determination of their molecular structures.…”

Section: Introductionmentioning

confidence: 98%

Oxidative addition reaction of o-quinones to triphenylantimony: novel triphenylantimony catecholate complexes

Cherkasov

Grunova

Poddel’sky

et al. 2005

Journal of Organometallic Chemistry

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“…Interestingly, a few reports have suggested that such species may form bimolecular adducts with Lewis bases. 9 Encouraged by these precedents, we have decided to study the properties of such compounds while also exploring the possibility of Lewis acid enhancement via the imposition of geometrical constraints. In this paper, we compare the properties of Ph 3 SbCl 2 with those of 5-phenyl-5,5-dichloro-λ 5 -dibenzostibole ( 1 ), 9a which can be regarded as a dichloride analogue of C and D , 9 two geometrically constrained compounds known to behave as antimony-based Lewis acids or, synonymously, pnictogen bond donors ( Chart 1 ).…”

Section: Introductionmentioning

confidence: 99%

Are Ar₃SbCl₂ Species Lewis Acidic? Exploration of the Concept and Pnictogen Bond Catalysis Using a Geometrically Constrained Example

Smith

Gabbaı̈

2023

Organometallics

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As part of our investigations into the Lewis acidic behavior of antimony derivatives, we have decided to study the properties of 5-phenyl-5,5dichloro-λ 5 -dibenzostibole (1), a dichlorostiborane with an antimony atom confined to a five-membered heterocycle. Our work shows that the resulting geometrical constraints elevate the Lewis acidity of the antimony atom, as confirmed by the crystal structure of 1-THF and the solution study of the interaction of 1 with Ph 3 PO. The enhanced Lewis acidic properties of 1, which exceed those of simple dichlorostiboranes such as Ph 3 SbCl 2 , also become manifest in pnictogen bonding catalysis experiments involving the reductions of imines with Hantzsch ester. The influence of geometrical constraints in the chemistry of this compound is also supported by a computational activation strain analysis as well as by an energy decomposition analysis of a model Me 3 PO adduct.

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New square-pyramidal organoantimony(V) compounds; crystal structures of (biphenyl-2,2′-diyl)phenylantimony(V) dibromide, dichloride and diisothiocyanate, Sb(2,2′-C12H8)PhX2 (X = Br, Cl or NCS), and of octahedral SbPh(o-O2C6Cl4)Cl2 ·OEt2

Cited by 26 publications

References 30 publications

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

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

Oxidative addition reaction of o-quinones to triphenylantimony: novel triphenylantimony catecholate complexes

Are Ar₃SbCl₂ Species Lewis Acidic? Exploration of the Concept and Pnictogen Bond Catalysis Using a Geometrically Constrained Example

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New square-pyramidal organoantimony(V) compounds; crystal structures of (biphenyl-2,2′-diyl)phenylantimony(V) dibromide, dichloride and diisothiocyanate, Sb(2,2′-C12H8)PhX2 (X = Br, Cl or NCS), and of octahedral SbPh(o-O2C6Cl4)Cl2 ·OEt2

Cited by 26 publications

References 30 publications

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

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

Oxidative addition reaction of o-quinones to triphenylantimony: novel triphenylantimony catecholate complexes

Are Ar3SbCl2 Species Lewis Acidic? Exploration of the Concept and Pnictogen Bond Catalysis Using a Geometrically Constrained Example

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Are Ar₃SbCl₂ Species Lewis Acidic? Exploration of the Concept and Pnictogen Bond Catalysis Using a Geometrically Constrained Example