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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F12%3A00384930%21RIV13-AV0-61388963
rdf:type
skos:Concept n13:Vysledek
dcterms:description
A series of mono- and 1,1'-diheteroatom-substituted ferrocene derivatives as well as acylated ferrocenes was prepared efficiently by a unified strategy that consists of selective mono- and 1,1'-dilithiation reactions and subsequent coupling with carbon, phosphorus, sulfur and halogen electrophiles. Chemical oxidation of the ferrocene derivatives by benzoquinone, 2,3-dichloro-5,6-dicyanobenzoquinone, AgPF6, or 2,2,6,6-tetramethyl-1-oxopiperidinium hexafluorophosphate provided the corresponding ferrocenium salts. The redox potentials of the synthesized ferrocenes were determined by cyclic voltammetry, and it was observed that all new ferrocenium salts have stronger oxidizing properties than standard ferrocenium hexafluorophosphate. An initial application of selected derivatives in an oxidative bicyclization revealed that they mediate the transformation under considerably milder conditions than ferrocenium hexafluorophosphate. Quantum chemical calculations of the reduction potentials of the substituted ferrocenium ions were carried out by using a standard thermodynamic cycle that involved the gas-phase energetics and solvation energies of the contributing species. A remarkable agreement between theory and experiment was found: the mean average deviation amounted to only 0.030 V and the maximum deviation to 0.1 V. This enabled the analysis of various physical contributions to the computed reduction potentials of these ferrocene derivatives, thereby providing insight into their electronic structure and physicochemical properties. A series of mono- and 1,1'-diheteroatom-substituted ferrocene derivatives as well as acylated ferrocenes was prepared efficiently by a unified strategy that consists of selective mono- and 1,1'-dilithiation reactions and subsequent coupling with carbon, phosphorus, sulfur and halogen electrophiles. Chemical oxidation of the ferrocene derivatives by benzoquinone, 2,3-dichloro-5,6-dicyanobenzoquinone, AgPF6, or 2,2,6,6-tetramethyl-1-oxopiperidinium hexafluorophosphate provided the corresponding ferrocenium salts. The redox potentials of the synthesized ferrocenes were determined by cyclic voltammetry, and it was observed that all new ferrocenium salts have stronger oxidizing properties than standard ferrocenium hexafluorophosphate. An initial application of selected derivatives in an oxidative bicyclization revealed that they mediate the transformation under considerably milder conditions than ferrocenium hexafluorophosphate. Quantum chemical calculations of the reduction potentials of the substituted ferrocenium ions were carried out by using a standard thermodynamic cycle that involved the gas-phase energetics and solvation energies of the contributing species. A remarkable agreement between theory and experiment was found: the mean average deviation amounted to only 0.030 V and the maximum deviation to 0.1 V. This enabled the analysis of various physical contributions to the computed reduction potentials of these ferrocene derivatives, thereby providing insight into their electronic structure and physicochemical properties.
dcterms:title
Acceptor-Substituted Ferrocenium Salts as Strong, Single-Electron Oxidants: Synthesis, Electrochemistry, Theoretical Investigations, and Initial Synthetic Application Acceptor-Substituted Ferrocenium Salts as Strong, Single-Electron Oxidants: Synthesis, Electrochemistry, Theoretical Investigations, and Initial Synthetic Application
skos:prefLabel
Acceptor-Substituted Ferrocenium Salts as Strong, Single-Electron Oxidants: Synthesis, Electrochemistry, Theoretical Investigations, and Initial Synthetic Application Acceptor-Substituted Ferrocenium Salts as Strong, Single-Electron Oxidants: Synthesis, Electrochemistry, Theoretical Investigations, and Initial Synthetic Application
skos:notation
RIV/61388963:_____/12:00384930!RIV13-AV0-61388963
n13:predkladatel
n19:ico%3A61388963
n4:aktivita
n9:P n9:I n9:Z
n4:aktivity
I, P(GA203/09/0705), Z(MSM0021620857)
n4:cisloPeriodika
39
n4:dodaniDat
n15:2013
n4:domaciTvurceVysledku
Mahamulkar, Shraddha G. Jahn, Ullrich Khobragade, Dushant n16:2834057 n16:7465157
n4:druhVysledku
n10:J
n4:duvernostUdaju
n11:S
n4:entitaPredkladatele
n12:predkladatel
n4:idSjednocenehoVysledku
120843
n4:idVysledku
RIV/61388963:_____/12:00384930
n4:jazykVysledku
n20:eng
n4:klicovaSlova
metallocenes; cyclic voltammetry; lactones; oxidation; redox chemistry
n4:klicoveSlovo
n6:oxidation n6:cyclic%20voltammetry n6:metallocenes n6:lactones n6:redox%20chemistry
n4:kodStatuVydavatele
DE - Spolková republika Německo
n4:kontrolniKodProRIV
[79BEF0A87769]
n4:nazevZdroje
Chemistry - A European Journal
n4:obor
n14:CC
n4:pocetDomacichTvurcuVysledku
5
n4:pocetTvurcuVysledku
6
n4:projekt
n8:GA203%2F09%2F0705
n4:rokUplatneniVysledku
n15:2012
n4:svazekPeriodika
18
n4:tvurceVysledku
Khobragade, Dushant Pospíšil, Lubomír Císařová, I. Jahn, Ullrich Rulíšek, Lubomír Mahamulkar, Shraddha G.
n4:wos
000308879000016
n4:zamer
n17:MSM0021620857
s:issn
0947-6539
s:numberOfPages
11
n3:doi
10.1002/chem.201201499