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• W2734765284 endingPage "8488" @default.
• W2734765284 startingPage "8476" @default.
• W2734765284 abstract "Second-order rate constants (k2) of the reactions of various barbiturate anions such as the parent barbiturate, 1,3-dimethylbarbiturate, 2-thiobarbiturate, and 1,3-diethyl-2-thiobarbiturate with diarylcarbenium ions and Michael acceptors have been determined in dimethyl sulfoxide solution at 20 °C. The reactivity parameters N and sN of the barbiturate anions were derived from the linear plots of log k2 versus the electrophilicity parameters E of these reference electrophiles, according to the linear-free-energy relationship log k2 (20 °C) = sN (E + N). Several reactions of these nucleophiles with benzylidenemalononitriles and quinone methides proceeded with reversible formation of the new C–C-bond followed by rate-determining proton shift. No evidence for initial attack of the electrophiles at the enolate oxygens of these nucleophiles was found by the kinetic measurements, in line with quantum chemical DFT calculations, which showed that in all cases C-attack is kinetically and thermodynamically preferred over O-attack. The nucleophilic reactivities of barbiturate anions were compared with those of structurally related carbanions, e.g., Meldrum’s acid and dimedone anions." @default.
• W2734765284 created "2017-07-21" @default.
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• W2734765284 date "2017-07-31" @default.
• W2734765284 modified "2023-10-11" @default.
• W2734765284 title "Kinetics of Electrophilic Alkylations of Barbiturate and Thiobarbiturate Anions" @default.
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• W2734765284 doi "https://doi.org/10.1021/acs.joc.7b01223" @default.
• W2734765284 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28715212" @default.
• W2734765284 hasPublicationYear "2017" @default.
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