Fischer aminocarbene complexes of chromium and iron: Anomalous electrochemical reduction of p-carbonyl substituted derivatives

This contribution shows how a small change of a remote substituent (COOCH 3 for e.g. OCH 3) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of π-electron delocalization and, consequently, redox properties of these potential catalysts. Du...

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Vydané v:	Electrochimica acta Ročník 56; číslo 19; s. 6853 - 6859
Hlavní autori:	Hoskovcová, Irena, Zvěřinová, Radka, Roháčová, Jana, Dvořák, Dalimil, Tobrman, Tomáš, Záliš, Stanislav, Ludvík, Jiří
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	Kidlington Elsevier Ltd 30.07.2011 Elsevier
Predmet:	Bonding Carbonyl and nitrosyl metals Chemistry Chromium Derivatives DFT calculations Electrochemistry Electrode potentials Electronics Exact sciences and technology Fischer aminocarbene complexes Fittings General and physical chemistry Inorganic chemistry and origins of life Iron Kinetics and mechanism of reactions LFER LUMO location Mathematical analysis Preparations and properties Electrochemistry LUMO location Fischer aminocarbene complexes LFER DFT calculations Chromium Organic compounds Chromium Carbonyl Complexes Orbital interaction Ylidene complex Chemical reduction Ester Carboxylic acid Chlorine Organic compounds Aminocarbene Electrochemical reaction Ether Frontier orbital Benzene derivatives Theoretical study Transition metal Carbonyl Complexes Iron Organic compounds Iron Carbonyl Complexes Density functional method Fluorine Organic compounds Kinetics
ISSN:	0013-4686, 1873-3859
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Abstract	This contribution shows how a small change of a remote substituent (COOCH 3 for e.g. OCH 3) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of π-electron delocalization and, consequently, redox properties of these potential catalysts. During investigation of redox properties of extended series of title compounds, an exceptionally positive reduction potential was observed (non fitting the LFER plot) for p-COOR substituents. This effect is caused by a strong intramolecular electronic interaction, which is specific for p-phenylene dicarbonyl compounds. In this context, the CN bond in aminocarbene moiety has a double bond character and resembles carbonyl function. The interpretation was proved by DFT calculations.
AbstractList	This contribution shows how a small change of a remote substituent (COOCH 3 for e.g. OCH 3) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of π-electron delocalization and, consequently, redox properties of these potential catalysts. During investigation of redox properties of extended series of title compounds, an exceptionally positive reduction potential was observed (non fitting the LFER plot) for p-COOR substituents. This effect is caused by a strong intramolecular electronic interaction, which is specific for p-phenylene dicarbonyl compounds. In this context, the CN bond in aminocarbene moiety has a double bond character and resembles carbonyl function. The interpretation was proved by DFT calculations. This contribution shows how a small change of a remote substituent (COOCH sub(3 for e.g. OCH) sub(3)) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of [pi]-electron delocalization and, consequently, redox properties of these potential catalysts. During investigation of redox properties of extended series of title compounds, an exceptionally positive reduction potential was observed (non fitting the LFER plot) for p-COOR substituents. This effect is caused by a strong intramolecular electronic interaction, which is specific for p-phenylene dicarbonyl compounds. In this context, the CN bond in aminocarbene moiety has a double bond character and resembles carbonyl function. The interpretation was proved by DFT calculations.
Author	Záliš, Stanislav Hoskovcová, Irena Zvěřinová, Radka Dvořák, Dalimil Ludvík, Jiří Tobrman, Tomáš Roháčová, Jana
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Cites_doi	10.1063/1.476673 10.1103/PhysRevA.38.3098 10.1021/om0605837 10.1063/1.464913 10.1016/j.electacta.2010.02.057 10.1016/j.electacta.2004.12.047 10.1007/BF00533485 10.1016/S0022-0728(68)80198-6 10.1021/om00011a027 10.1039/c0cc02337j 10.1021/om00011a022
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Keywords	Electrochemistry LUMO location Fischer aminocarbene complexes LFER DFT calculations Chromium Organic compounds Chromium Carbonyl Complexes Orbital interaction Ylidene complex Chemical reduction Ester Carboxylic acid Chlorine Organic compounds Aminocarbene Electrochemical reaction Ether Frontier orbital Benzene derivatives Theoretical study Transition metal Carbonyl Complexes Iron Organic compounds Iron Carbonyl Complexes Density functional method Fluorine Organic compounds Kinetics
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Snippet	This contribution shows how a small change of a remote substituent (COOCH 3 for e.g. OCH 3) on Fischer aminocarbene complexes can change totally the LUMO... This contribution shows how a small change of a remote substituent (COOCH sub(3 for e.g. OCH) sub(3)) on Fischer aminocarbene complexes can change totally the...
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SubjectTerms	Bonding Carbonyl and nitrosyl metals Chemistry Chromium Derivatives DFT calculations Electrochemistry Electrode potentials Electronics Exact sciences and technology Fischer aminocarbene complexes Fittings General and physical chemistry Inorganic chemistry and origins of life Iron Kinetics and mechanism of reactions LFER LUMO location Mathematical analysis Preparations and properties
Title	Fischer aminocarbene complexes of chromium and iron: Anomalous electrochemical reduction of p-carbonyl substituted derivatives
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