Comparison of the Electrophilic Reactivities of  N ‐Acylpyridinium Ions and Other Acylating Agents | Zendy

Nigst Tobias A. | Zendy; Mayr Herbert | Zendy

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Comparison of the Electrophilic Reactivities of N ‐Acylpyridinium Ions and Other Acylating Agents

Author(s) -

Nigst Tobias A.,

Mayr Herbert

Publication year - 2013

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.201201540

Subject(s) - nucleophile , chemistry , carbanion , electrophile , acetonitrile , medicinal chemistry , dimethyl sulfoxide , acylation , carboxylate , organic chemistry , catalysis

The kinetics of the reactions of carbanions, carboxylate anions, and primary and secondary amines with acylating agents were studied in acetonitrile and dimethyl sulfoxide (DMSO) under first‐order conditions by UV/Vis spectrophotometry and conductimetry. Whereas reactions of a large variety of nucleophiles with ordinary carbanions and Michael acceptors generally follow the linear free energy relationship lg k 2 (20 °C) = s N ( N + E ), separate correlation lines for different types of nucleophiles were found when (lg k 2 )/ s N was plotted against N for the reactions with acyl derivatives 2 – 5 . Even when nucleophilic attack is rate determining, the reactivities of acylating agents towards nucleophiles cannot be described by a single set of nucleophile‐independent electrophilicity parameters.

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