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Ambident Reactivities of Methylhydrazines
Author(s) -
Nigst Tobias A.,
Ammer Johannes,
Mayr Herbert
Publication year - 2012
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.201107315
Subject(s) - reactivity (psychology) , nucleophile , nitrogen atom , chemistry , nitrogen , kinetics , position (finance) , content (measure theory) , group (periodic table) , medicinal chemistry , organic chemistry , physics , mathematics , catalysis , medicine , economics , alternative medicine , pathology , quantum mechanics , mathematical analysis , finance
Kinetics versus thermodynamics : Methyl groups increase the nucleophilic reactivity of the substituted position of hydrazines and reduce the nucleophilicity of the adjacent nitrogen center. As a result, the tertiary nitrogen atom of 1,1‐dimethylhydrazine is 3000 times more reactive than the NH 2 group, but under thermodynamic control substitution of an NH 2 proton occurs (see picture).