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Cover Picture: Structure–Nucleophilicity Relationships for Enamines (Chem. Eur. J. 10/2003)
Author(s) -
Kempf Bernhard,
Hampel Nathalie,
Ofial Armin R.,
Mayr Herbert
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390220
Subject(s) - nucleophile , electrophile , chemistry , cover (algebra) , enamine , cyclohexene , computational chemistry , value (mathematics) , medicinal chemistry , organic chemistry , catalysis , mathematics , mechanical engineering , engineering , statistics
The cover picture shows the exponential decay of the UV/Vis absorption of a diarylmethyl cation in presence of 46 equivalents of 1‐(methylphenylamino)cyclohexene. Using diarylmethyl cations of different electrophilicity E allows us to perform a comprehensive comparison of enamine nucleophilicity ( N ) on the basis of the depicted correlation equation. Enamines, commonly characterized as strong nucleophiles, show dramatically different reactivities. For a typical s value of 0.85, the nucleophilicity range from N = 16 to N = 4 corresponds to relative reactions times of one minute versus 20 000 years. A detailed report on the relationships between structure and nucleophilicities of enamines is given by H. Mayr et al. on p. 2209 ff.