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• W2321874125 abstract "Imidazolin-2-imines (ImRN-), derived from N-heterocyclic carbenes, have been shown to be strong electron donors when directly coordinated to metals or when used as a substituent in larger ligand frameworks. In an attempt to enhance the electron-donating properties of the guanidine ligand class, the effect of appending an ImRN- backbone onto a guanidinate scaffold was investigated. Addition of 1 equiv of [Li(Et2O)][ImtBuN] to the aryl carbodiimide (dippN)2C (dipp = 2,6-diisopropylphenyl) cleanly affords the lithium ImtBuN-functionalized guanidinate [Li(THF)2][(ImtBuN)C(Ndipp)2] (1). Subsequent metalation of the ligand with FeBr2 gives the yellow Fe(II) complex {[(ImtBuN)C(Ndipp)2]FeBr}2 (4) in good yield. Solid-state structural analyses of 1 and 4 show the ImtBuN- group acts as a non-coordinating backbone substituent. Direct structural comparison of 4 to the closely related guanidinate and ketimine-guanidinate complexes {[(X)C(Ndipp)2]FeBr}2 (X = tBu2C=N (5); N(iPr)2 (6)), differing only in their backbone, reveals a resonance contribution of the ImtBuN- group to the guanidinate ligand electronic structure. Moreover, the Fe(II)/Fe(III) redox couple of 4 (E1/2 = −0.67 V) is cathodically shifted by greater than 200 mV from the oxidation potentials of 5 (E1/2 = −0.42 V) and 6 (E1/2 = −0.45 V), demonstrating the [(ImtBuN)C(Ndipp)2]− system to be a quantifiably superior electron donor." @default.
• W2321874125 created "2016-06-24" @default.
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• W2321874125 date "2016-04-04" @default.
• W2321874125 modified "2023-09-25" @default.
• W2321874125 title "Advances in guanidine ligand design: synthesis of a strongly electron-donating, imidazolin-2-iminato functionalized guanidinate and its properties on iron" @default.
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• W2321874125 doi "https://doi.org/10.1080/00958972.2016.1167198" @default.
• W2321874125 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/5312970" @default.
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