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Generating and Trapping Metalla‐N‐Heterocyclic Carbenes
Author(s) -
Ruiz Javier,
García Lucía,
Vivanco Marilín,
Berros Ángela,
Van der Maelen Juan Francisco
Publication year - 2015
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.201411647
Subject(s) - carbene , chemistry , singlet state , trapping , transition metal , metal , proton , computational chemistry , photochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , excited state , ecology , physics , quantum mechanics , nuclear physics , biology
By means of a combined experimental and theoretical approach, the electronic features and chemical behavior of metalla‐N‐heterocyclic carbenes (MNHCs, N‐heterocyclic carbenes containing a metal atom within the heterocyclic skeleton) have been established and compared with those of classical NHCs. MNHCs are strongly basic (proton affinity and p K a values around 290 kcal mol −1 and 36, respectively) with a narrow singlet–triplet gap (around 23 kcal mol −1 ). MNHCs can be generated from the corresponding metalla‐imidazolium salts and trapped by addition of transition‐metal complexes affording the corresponding heterodimetallic dicarbene derivatives, which can serve as carbene transfer agents.