Electronic effects in 4-substituted bis(imino)pyridines and the corresponding reduced iron compounds

Jonathan M. Darmon; Zoë R. Turner; Emil Lobkovsky; Paul J. Chirik

doi:10.1021/om201212m

Electronic effects in 4-substituted bis(imino)pyridines and the corresponding reduced iron compounds

Jonathan M. Darmon, Zoë R. Turner, Emil Lobkovsky, Paul J. Chirik

Chemistry

Research output: Contribution to journal › Article › peer-review

69 Scopus citations

Abstract

A family of 4-substituted bis(imino)pyridines, 4-X- ^iPrPDI (4-X- ^iPrPDI = 2,6-(2,6- ⁱPr ₂-C ₆H ₃N=CMe) ₂-4-X-C ₅H ₂N; X = CF ₃, ^tBu, Bn, NMe ₂), has been synthesized and the iron coordination chemistry studied. Sodium amalgam reduction of the iron dihalides (4-X- ^iPrPDI)FeX ₂ (X = Cl, Br) in the presence of excess carbon monoxide furnished the corresponding iron dicarbonyl compounds (4-X- ^iPrPDI)Fe(CO) ₂. Equilibrium mixtures of the four- and five-coordinate iron dinitrogen compounds (4-X- ^iPrPDI)FeN ₂ and (4-X- ^iPrPDI)Fe(N ₂) ₂ were prepared by performing the sodium amalgam reduction of the iron dihalides under a dinitrogen atmosphere. Electrochemical and spectroscopic measurements were conducted on the free ligands and the iron derivatives to systematically evaluate the influence of each para pyridine substituent on the electronic structure of the compound.

Original language	English (US)
Pages (from-to)	2275-2285
Number of pages	11
Journal	Organometallics
Volume	31
Issue number	6
DOIs	https://doi.org/10.1021/om201212m
State	Published - Mar 26 2012

All Science Journal Classification (ASJC) codes

Inorganic Chemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/om201212m

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@article{5d338756894f4f0985e3d3c1b3e9486a,

title = "Electronic effects in 4-substituted bis(imino)pyridines and the corresponding reduced iron compounds",

abstract = "A family of 4-substituted bis(imino)pyridines, 4-X- iPrPDI (4-X- iPrPDI = 2,6-(2,6- iPr 2-C 6H 3N=CMe) 2-4-X-C 5H 2N; X = CF 3, tBu, Bn, NMe 2), has been synthesized and the iron coordination chemistry studied. Sodium amalgam reduction of the iron dihalides (4-X- iPrPDI)FeX 2 (X = Cl, Br) in the presence of excess carbon monoxide furnished the corresponding iron dicarbonyl compounds (4-X- iPrPDI)Fe(CO) 2. Equilibrium mixtures of the four- and five-coordinate iron dinitrogen compounds (4-X- iPrPDI)FeN 2 and (4-X- iPrPDI)Fe(N 2) 2 were prepared by performing the sodium amalgam reduction of the iron dihalides under a dinitrogen atmosphere. Electrochemical and spectroscopic measurements were conducted on the free ligands and the iron derivatives to systematically evaluate the influence of each para pyridine substituent on the electronic structure of the compound.",

author = "Darmon, {Jonathan M.} and Turner, {Zo{\"e} R.} and Emil Lobkovsky and Chirik, {Paul J.}",

year = "2012",

month = mar,

day = "26",

doi = "10.1021/om201212m",

language = "English (US)",

volume = "31",

pages = "2275--2285",

journal = "Organometallics",

issn = "0276-7333",

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TY - JOUR

T1 - Electronic effects in 4-substituted bis(imino)pyridines and the corresponding reduced iron compounds

AU - Darmon, Jonathan M.

AU - Turner, Zoë R.

AU - Lobkovsky, Emil

AU - Chirik, Paul J.

PY - 2012/3/26

Y1 - 2012/3/26

N2 - A family of 4-substituted bis(imino)pyridines, 4-X- iPrPDI (4-X- iPrPDI = 2,6-(2,6- iPr 2-C 6H 3N=CMe) 2-4-X-C 5H 2N; X = CF 3, tBu, Bn, NMe 2), has been synthesized and the iron coordination chemistry studied. Sodium amalgam reduction of the iron dihalides (4-X- iPrPDI)FeX 2 (X = Cl, Br) in the presence of excess carbon monoxide furnished the corresponding iron dicarbonyl compounds (4-X- iPrPDI)Fe(CO) 2. Equilibrium mixtures of the four- and five-coordinate iron dinitrogen compounds (4-X- iPrPDI)FeN 2 and (4-X- iPrPDI)Fe(N 2) 2 were prepared by performing the sodium amalgam reduction of the iron dihalides under a dinitrogen atmosphere. Electrochemical and spectroscopic measurements were conducted on the free ligands and the iron derivatives to systematically evaluate the influence of each para pyridine substituent on the electronic structure of the compound.

AB - A family of 4-substituted bis(imino)pyridines, 4-X- iPrPDI (4-X- iPrPDI = 2,6-(2,6- iPr 2-C 6H 3N=CMe) 2-4-X-C 5H 2N; X = CF 3, tBu, Bn, NMe 2), has been synthesized and the iron coordination chemistry studied. Sodium amalgam reduction of the iron dihalides (4-X- iPrPDI)FeX 2 (X = Cl, Br) in the presence of excess carbon monoxide furnished the corresponding iron dicarbonyl compounds (4-X- iPrPDI)Fe(CO) 2. Equilibrium mixtures of the four- and five-coordinate iron dinitrogen compounds (4-X- iPrPDI)FeN 2 and (4-X- iPrPDI)Fe(N 2) 2 were prepared by performing the sodium amalgam reduction of the iron dihalides under a dinitrogen atmosphere. Electrochemical and spectroscopic measurements were conducted on the free ligands and the iron derivatives to systematically evaluate the influence of each para pyridine substituent on the electronic structure of the compound.

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U2 - 10.1021/om201212m

DO - 10.1021/om201212m

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AN - SCOPUS:84859151123

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JO - Organometallics

JF - Organometallics

IS - 6

ER -

Electronic effects in 4-substituted bis(imino)pyridines and the corresponding reduced iron compounds

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