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Calcium Hydride Reactivity: Formation of an Anionic N‐Heterocyclic Olefin Ligand
Author(s) -
Causero Andrea,
Elsen Holger,
Pahl Jürgen,
Harder Sjoerd
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703037
Subject(s) - deprotonation , chemistry , ligand (biochemistry) , olefin fiber , reactivity (psychology) , bifunctional , hydride , medicinal chemistry , aromaticity , stereochemistry , organic chemistry , molecule , ion , metal , receptor , medicine , biochemistry , alternative medicine , pathology , catalysis , polymer
An anionic N‐heterocyclic olefin ligand was serendipitously obtained by reaction of an amidinate calcium hydride complex with 1,3‐dimethyl‐2‐methyleneimidazole (NHO). Instead of anticipated addition to the polarized C=CH 2 bond to form an unstabilized alkylcalcium complex, deprotonation of the NHO ligand in the backbone was observed. Preference for deprotonation versus addition is explained by loss of aromaticity in the latter conversion. Theoretical calculations demonstrate the substantially increased ylidic character of this anionic NHO ligand which, like N‐heterocyclic dicarbenes, shows strong bifunctional coordination.