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Enhancing the Reactivity of an Electrophilic Barbiturate Dye by Cooperative Hydrogen Bonding
Author(s) -
Bauer Mirko,
Spange Stefan
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901066
Subject(s) - chemistry , electrophile , nucleophile , reactivity (psychology) , barbiturate , hydrogen bond , photochemistry , supramolecular chemistry , cyanide , computational chemistry , organic chemistry , catalysis , molecule , medicine , psychology , alternative medicine , pathology , psychiatry
The supramolecular complex formation by cooperativehydrogen bonding of a highly dipolar barbiturate dye and 2,6‐diacetamidopyridine is shown to have a marked effect on the reactivity of the barbiturate. The increase of both Lewis acidity and electrophilicity by hydrogen bonding is demonstrated by thermodynamic and kinetic studies using the electrophile–nucleophile recombination reaction with cyanide.