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Imidazol‐2‐ylidene: Generation of a Missing Carbene and Its Dication by Neutralization–Reionizatin and Charge‐Stripping Mass Spectrometry
Author(s) -
McGibbon Graham A.,
Heinemann Christoph,
Lavorato David J.,
Schwarz Helmut
Publication year - 1997
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.199714781
Subject(s) - dication , carbene , chemistry , neutralization , mass spectrometry , reionization , imidazole , molecule , acetonitrile , aldehyde , hydrogen , photochemistry , computational chemistry , catalysis , ionization , stereochemistry , organic chemistry , ion , chromatography , antibody , immunology , biology
Though not yet available off‐the‐shelf , the generation the title molecule 2 from aldehyde 1 and its detection in the gas phase confirms quantum chemical predictions that it should be stable, in particular towards its 1,2‐hydrogen shift isomer imidazole. Thus, substituents larger than hydrogen on the nitrogen atoms are not a feature essential to the inherent stability of imidazolylidene carbenes, although such groups may still play a role in hindering bimolecular processes (N = neutralization, R = reionization).