Literature DB >> 17592845

Copper(I)/S(8) reversible reactions leading to an end-on bound dicopper(II) disulfide complex: nucleophilic reactivity and analogies to copper-dioxygen chemistry.

Debabrata Maiti1, Julia S Woertink, Michael A Vance, Ashley E Milligan, Amy A Narducci Sarjeant, Edward I Solomon, Kenneth D Karlin.   

Abstract

Elemental sulfur (S8) reacts reversibly with the copper(I) complex [(TMPA')CuI](+) (1), where TMPA' is a TMPA (tris(2-pyridylmethyl)amine) analogue with a 6-CH2OCH3 substituent on one pyridyl ligand arm, affording a spectroscopically pure end-on bound disulfido-dicopper(II) complex [{(TMPA')Cu(II)}2(mu-1,2-S2(2-))](2+) (2) {nu(S-S) = 492 cm(-1); nu(Cu-S)sym = 309 cm(-1)}; by contrast, [(TMPA)Cu(I)(CH3CN)](+) (3)/S8 chemistry produces an equilibrium mixture of at least three complexes. The reaction of excess PPh3 with 2 leads to formal "release" of zerovalent sulfur and reduction of copper ion to give the corresponding complex [(TMPA')Cu(I)(PPh3)](+) (11) along with S=PPh3 as products. Dioxygen displaces the disulfur moiety from 2 to produce the end-on Cu2O2 complex, [{(TMPA')Cu(II)}2(mu-1,2-O2(2-)](2+) (9). Addition of the tetradentate ligand TMPA to 2 generates the apparently more thermodynamically stable [{(TMPA)Cu(II)}2(mu-1,2-S2(2-))](2+) (4) and expected mixture of other species. Bubbling 2 with CO leads to the formation of the carbonyl adduct [(TMPA')CuI(CO)](+) (8). Carbonylation/sulfur-release/CO-removal cycles can be repeated several times. Sulfur atom transfer from 2 also occurs in a near quantitative manner when it is treated with 2,6-dimethylphenyl isocyanide (ArNC), leading to the corresponding isothiocyanate (ArNCS) and [(TMPA')Cu(I)(CNAr)](+) (12). Complex 2 readily reacts with PhCH2Br: [{(TMPA')Cu(II)}2(mu-1,2-S(2)(2-)](2+) (2) + 2 PhCH2Br --> [{(TMPA')Cu(II)(Br)}2](2+) (6) + PhCH2SSCH2Ph. The unprecedented substrate reactivity studies reveal that end-on bound mu-1,2-disulfide-dicopper(II) complex 2 provides a nucleophilic S2(2-) moiety, in striking contrast to the electrophilic behavior of a recently described side-on bound mu-eta(2):eta(2)-disulfido-dicopper(II) complex, [{(N3)Cu(II)}(2)(mu-eta(2):eta(2)-S2(2-))](2+) (5) with tridentate N3 ligand. The investigation thus reveals striking analogies of copper/sulfur and copper/dioxygen chemistries, with regard to structure type formation and specific substrate reactivity patterns.

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Year:  2007        PMID: 17592845     DOI: 10.1021/ja071968z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Systematic characterization on electronic structures and spectra for a series of complexes, M(IDB)Cl2 (M = Mn, Fe, Co, Ni, Cu and Zn): a theoretical study.

Authors:  Yanyan Zhu; Zhanfen Chen; Zijian Guo; Yan Wang; Guangju Chen
Journal:  J Mol Model       Date:  2008-12-13       Impact factor: 1.810

2.  Molecular oxygen and sulfur reactivity of a cyclotriveratrylene derived trinuclear copper(I) complex.

Authors:  Debabrata Maiti; Julia S Woertink; Reza A Ghiladi; Edward I Solomon; Kenneth D Karlin
Journal:  Inorg Chem       Date:  2009-09-07       Impact factor: 5.165

3.  Copper-hydroperoxo-mediated N-debenzylation chemistry mimicking aspects of copper monooxygenases.

Authors:  Debabrata Maiti; Amy A Narducci Sarjeant; Kenneth D Karlin
Journal:  Inorg Chem       Date:  2008-09-11       Impact factor: 5.165

4.  Crystal structure of [tris-(pyridin-2-ylmeth-yl)amine-κ(4) N]copper(II) bromide.

Authors:  Emma C Bridgman; Megan M Doherty; Kaleigh A Ellis; Elizabeth A Homer; Taylor N Lashbrook; Margaret E Mraz; Gina C Pernesky; Emma M Vreeke; Kayode D Oshin; Allen G Oliver
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-05-10
  4 in total

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