Aryl- and hetaryl-containing amide anions in reactions of aromatic nucleophilic substitution

Aryl- and hetaryl-containing amide anions in reactions of aromatic nucleophilic substitution Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 1995, Volume: 44, Number: 12, Pages: 2211-2215 Pages count : 5 DOI: 10.1007/BF00713583

Tags

aryl-containing amide anions; aryl halides; SNAr reactions; phase transfer catalysis; Bronsted coefficient

Authors

Vlasov V.M. ¹ , Oskina I.A. ¹ , Landini D. ² , Maia A. ²

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation
2	Department of Organic and Industrial Chemistry, University of Milan, via Golgi 19, 20133, Milan, Italy

The results of kinetic studies of SNAr reactions of p-nitrohalobenzenes, hexafluorobenzene, and pentafluoropyridine with aryl-, diaryl-, and hetarylamide anions under homogeneous conditions (in dimethyl sulfoxide) and under conditions of phase transfer catalysis (in toluene) are analyzed. The increase in the Bronsted coefficient beta(Nu) in reactions of amide anions in DMSO as the electrophilicity of the substrate increases and steric hindrance in nucleophiles decreases may result from a higher degree of charge transfer from a nucleophile to a substrate in the transition state. The possibility of replacement of the SNAr by the SET mechanism in these reaction is discussed.

Vlasov V.M. , Oskina I.A. , Landini D. , Maia A.
Aryl- and hetaryl-containing amide anions in reactions of aromatic nucleophilic substitution
Russian Chemical Bulletin. 1995. V.44. N12. P.2211-2215. DOI: 10.1007/BF00713583 WOS Scopus РИНЦ

Published print:

Dec 1, 1995

Web of science	WOS:A1995UE90700001
Scopus	2-s2.0-40449103382
Elibrary	28533413
OpenAlex	W2952137757