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[(α‐Cyanobenzyllithium. Tetramethylethylenediamine) 2 . Benzene]: X‐ray Structure Analysis of an α‐Nitrile “Carbanion”
Author(s) -
Boche Gernot,
Marsch Michael,
Harms Klaus
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198603731
Subject(s) - carbanion , ketene , tetramethylethylenediamine , nitrile , chemistry , benzene , enol , medicinal chemistry , double bond , x ray , photochemistry , polymer chemistry , organic chemistry , catalysis , physics , quantum mechanics
A “ketene iminate”and not a carbanionis present in the title compound 1 ·C 6 H 6 . The bond lengths in the CCN group deviate considerably from those in ketene imines such as 2 . In comparison, enolates have practically the same bond lengths as enol ethers. This difference is due to the different stabilization of a negative charge by nitriles and carbonyl compounds.