1,4-Bis(phosphine)-2,5-difluoro-3,6-dihydroxybenzenes and their P-oxides: Syntheses, structures, ligating and electronic properties

Pignotti, Louis R.; Kongprakaiwoot, Natcharee; Brennessel, William W.; Baltrušaitis, Jonas; Luck, Rudy L.; Urnéžius, Eugenijus

doi:10.1016/j.jorganchem.2008.07.023

Cited by 20 publications

(15 citation statements)

References 62 publications

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“…Efforts to generate benzosemiquinonoid-containing transition metal complexes with a nuclearity of greater than one have resulted in numerous dinuclear compounds, including those containing metal centers bridged by derivatives of 2,5-dihydroxy-1,4-benzoquinonoids [172][173][174][175][176][177][178][179][180][181][182][183][184][185][186][187][188][189], bis(pyrazolyl)benzoquinonoids [190][191][192][193], bis(phosphine)benzoquinonoids [194,195], bis(amino) benzoquinonoids [196][197][198][199][200][201][202], and bis(amino)diiminobenzoquinonoids [86,[203][204][205][206]. Indeed, the radical form of these ligands has shown enhanced magnetic coupling compared to their non-radical redox isomers [174,180,182].…”

Section: Benzosemiquinonoid Radical-bridged Single-molecule Magnetsmentioning

confidence: 99%

Radical ligand-containing single-molecule magnets

Demir

Jeon

Long

et al. 2015

Coordination Chemistry Reviews

542

386

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Section: Benzosemiquinonoid Radical-bridged Single-molecule Magnetsmentioning

confidence: 99%

Radical ligand-containing single-molecule magnets

Demir

Jeon

Long

et al. 2015

Coordination Chemistry Reviews

542

386

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“…General Procedures: Ligand 1b [2,5‐bis(diisopropylphosphoryl)‐3,6‐difluoro‐1,4‐hydroquinone]12 and copper complexes (bipy)CuCl 2 30 and (bipy)Cu(CH 3 COO) 2 31 were prepared according to published procedures. Other reagents and solvents were bought from commercial suppliers and were used as received.…”

Section: Methodsmentioning

confidence: 99%

“…Some time ago we have reported on the syntheses of two 2,5‐bis(phosphanyl)‐3,6‐difluoro‐1,4‐hydroquinones and of their P‐oxides 12. The P‐oxides, namely 2,5‐bis(diphenylphosphoryl)‐3,6‐difluoro‐1,4‐hydroquinone ( 1a ) and 2,5‐bis(diisopropylphosphoryl)‐3,6‐difluoro‐1,4‐hydroquinone ( 1b ) were anticipated to display coordination properties similar to those of diamine‐appended 1,4‐hydroquinones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1‐Arylnaphthalenes by Gold‐Catalyzed One‐Pot Sequential Epoxide to Carbonyl Rearrangement and Cyclization with Arylalkynes

Gudla

Balamurugan

2012

Chemistry An Asian Journal

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“…[31][32][33][34][35][36][37][38][39][40][41][42] However, other hydroquinone derivatives 2 and 3 (Scheme 2) possesses redox characteristics more like 1,4-hydroquinone (i.e., higher potential, irreversible oxidations) despite the fact that both of these derivatives also possess intramolecular hydrogen bonds. [43][44][45] The contrasting redox behavior between 1 and 2 and 3 raises questions concerning (1) the generality of the effect of intramolecular hydrogen bonds on QH 2 redox properties and (2) the nature of the oxidized forms of the hydroquinones, i.e., are they isolable and, if so, what are their structures? Herein we present a study of several intramolecularly hydrogen-bonded hydroquinone derivatives (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

Unconventional redox properties of hydroquinones with intramolecular OH−N hydrogen bonds

et al. 2014

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The redox (chemical and electrochemical) properties of several hydroquinones are reported in which the OH protons are engaged in intramolecular hydrogen bonds to a nitrogen-based acceptor (pyridine or amine). The 1,4-hydroquinones generally undergo reversible oxidation to quinones in which both OH protons have transferred to the pendant bases; the oxidation processes are generally chemically and electrochemically reversible, in stark contrast with normal hydroquinones, which are oxidized irreversibly (via proton loss) to quinones. The oxidation processes, believed to occur in concerted proton/electron transfer steps, are at much lower potentials for the hydrogen-bonded derivatives relative to unsubstituted derivatives. In contrast, isomeric 1,3-hydroquinones (resorcinols) are oxidized irreversibly at relatively high potentials. The stability of some of the 1,4-hydroquinone oxidized species permits their isolation and characterization both spectroscopically and structurally. Somewhat surprisingly, in the oxidized species in which the proton is now located on the nitrogen base, the characterization data indicate that there is no NH−O hydrogen bond. Relationships between the particulars of the redox properties of the hydroquinones (potentials, reversibility/stability) and molecular structure are discussed.Résumé : Les propriétés redox (chimiques et électrochimiques) de plusieurs hydroquinones sont décrites, dans lesquelles les protons OH participent à des liaisons hydrogènes intramoléculaires avec un accepteur à base d'azote (pyridine ou amine). Les 1,4-hydroquinones subissent en général une oxydation réversible qui produit des quinones dans lesquelles les deux protons OH ont été transférés aux bases correspondantes. Les processus d'oxydation sont généralement chimiquement et électrochimique-ment réversibles, à l'opposé des hydroquinones normales qui sont oxydées de manière irréversible (par perte de proton) sous la forme de quinones. Les processus d'oxydation, dont on pense qu'ils se produisent selon des étapes de transfert concerté de proton/électron, présentent des potentiels beaucoup plus bas dans le cas des dérivés comportant des liaisons hydrogènes que dans celui des dérivés non substitués. En revanche, les 1,3-hydroquinones isomériques (résorcinols) sont oxydées de manière irréversible à des potentiels relativement élevés. La stabilité de quelques-unes des 1,4-hydroquinones oxydées permet de les isoler et de les caractériser structurellement et par spectroscopie. De façon quelque peu surprenante, les données de caractérisation indiquent que les espèces oxydées, dans lesquelles le proton est désormais situé sur la base azotée, ne possèdent pas de liaisons hydrogènes NH−O. Les liens entre les propriétés redox détaillées des hydroquinones (potentiels, réversibilité/stabilité) et la structure moléculaire sont analysés. [Traduit par la Rédaction]

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1,4-Bis(phosphine)-2,5-difluoro-3,6-dihydroxybenzenes and their P-oxides: Syntheses, structures, ligating and electronic properties

Cited by 20 publications

References 62 publications

Radical ligand-containing single-molecule magnets

Radical ligand-containing single-molecule magnets

Synthesis of 1‐Arylnaphthalenes by Gold‐Catalyzed One‐Pot Sequential Epoxide to Carbonyl Rearrangement and Cyclization with Arylalkynes

Unconventional redox properties of hydroquinones with intramolecular OH−N hydrogen bonds

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