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Pissarev, S. A.; Shevchenko, Nikolay E.; Nenaidenko, V. G.; Баленкова, Е. С.

doi:10.1023/a:1026071713521

Cited by 4 publications

(2 citation statements)

References 13 publications

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“…Reactions of electrophilic addition, in general, and of protonation, in particular, have been theoretically investigated in a number of cases, usually involving free nucleophiles. They include halogenation of olefins, alkynes, and allenes, reaction of S 2 2+ with alkenes, protonation of olefins, alkanes, ketenes, thiouracils, chlorine nitrate, phenanthrolines, macrocycles, quinolines, benzazepines, and acetanilides, boranes, and thiazoles, and anti-Mills−Nixon systems . Less studied is the electrophilic addition to a substrate activated upon coordination, examples including interaction of weak acids and aldehydes with bis-allylpalladium complexes, addition of CO 2 to 2-lithio-1,3-dithiane, addition of methyl cation to arene tricarbonylchromium complexes, and protonation of η 2 -allene, of η 2 -alkynes, of biological macromolecules, and of titanium peroxo complexes .…”

Section: Resultsmentioning

confidence: 99%

Protic Conversion of Nitrile into Azavinylidene Complexes of Rhenium, a Mechanistic Theoretical Study

2005

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The mechanism of the protonation of the rhenium nitrile chloro-complexes [ReCl(NCCH3)(PH3)4] (2), taken as models of the real systems [ReCl(NCR)(dppe)(2)] (dppe = Ph2PCH2CH2PPh2), leading to the azavinylidene products [ReCl(NC(H)CH3)(PH3)4]+ (3) was investigated by theoretical methods at the B3LYP level of theory. Electrostatic and molecular orbital arguments and thermodynamic, kinetic, and steric factors are analyzed and indicate that the chlorine atom is the most probable site of the initial proton attack, although the direct protonation of the nitrile carbon atom is also possible as a concurrent process. For the cis-isomer of 2, the initially formed chloro-protonated species cis-[Re(ClH)(NCCH3)(PH3)4]+ further converts to the azavinylidene cis-3 via either an acid-independent 1,4-proton shift or an acid-base catalyzed pathway involving a second protonation of the nitrile carbon atom to give cis-[Re(ClH)(NC(H)CH3)(PH3)4]2+ followed by elimination of the proton from the chlorine atom.

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Section: Resultsmentioning

confidence: 99%

Protic Conversion of Nitrile into Azavinylidene Complexes of Rhenium, a Mechanistic Theoretical Study

2005

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“…Chemical oxidation of 7b produced the corresponding Te−Te bonded dication as deduced from 1 H, 13 C, and 125 Te NMR spectroscopic studies. Ab initio molecular orbital calculations on the dications derived from 1a − f with a transannular chalcogen−chalcogen bond were reported …”

Section: Introductionmentioning

confidence: 99%

Electrochemical and Chemical Oxidation of Dithia-, Diselena-, Ditellura-, Selenathia-, and Tellurathiamesocycles and Stability of the Oxidized Species

et al. 2010

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The diverse electrochemical and chemical oxidations of dichalcogena-mesocycles are analyzed, broadening our understanding of the chemistry of the corresponding radical cations and dications. 1,5-Diselenocane and 1,5-ditellurocane undergo reversible two-electron oxidation with inverted potentials analogous to 1,5-dithiocane. On the other hand, 1,5-selenathiocane and 1,5-tellurathiocane undergo one-electron oxidative dimerization. The X-ray crystal structures of the Se-Se dimer of the 1,5-selenathiocane one-electron oxidized product and the monomeric two-electron oxidized product (dication) of 1,5-tellurathiocane are reported. 1,5-Dithiocanes and 1,5-diselenocanes with group 14 atoms as ring members undergo irreversible oxidation, unlike the reversible two-electron oxidation of the corresponding silicon-containing 1,5-ditellurocanes. These results demonstrate the chemical consequences of the dication stabilities Te(+)-Te(+) > Se(+)-Se(+) > S(+)-S(+), as well as Se(+)-Se(+) > Se(+)-S(+) and Te(+)-Te(+) > Te(+)-S(+).

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Bicyclic Systems with Bridgehead (Ring Junction) Sulfur, Selenium, or Tellurium Atoms

Forristal

2008

Comprehensive Heterocyclic Chemistry III

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Cited by 4 publications

References 13 publications

Protic Conversion of Nitrile into Azavinylidene Complexes of Rhenium, a Mechanistic Theoretical Study

Protic Conversion of Nitrile into Azavinylidene Complexes of Rhenium, a Mechanistic Theoretical Study

Electrochemical and Chemical Oxidation of Dithia-, Diselena-, Ditellura-, Selenathia-, and Tellurathiamesocycles and Stability of the Oxidized Species

Bicyclic Systems with Bridgehead (Ring Junction) Sulfur, Selenium, or Tellurium Atoms

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