The kinetics of the reactions of some 2-L-5-nitro-3-X-thiophenes with primary and secondary amines in methanol at various temperatures have been studied with the aim of obtaining information about the proximity effects of 3-X ortho-like substituents. The results obtained have shown that for all the substituents considered, except for X = Br, the proximity effects of steric nature are of little relevance with respect to the electronic ones. Thus, it has been possible to establish a set of ortho sigma constants which account well for the electronic effects of 3-X substituents and to obtain excellent linear free energy ortho-correlations.
Consiglio G., Frenna V., Guernelli S., Macaluso G., Spinelli D. (2002). Analysis of substituent effects: The reactions of some 2-L-5-nitro-3-X-thiophenes with primary and secondary amines in methanol. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2, 5, 965-970 [10.1039/b111541c].
Analysis of substituent effects: The reactions of some 2-L-5-nitro-3-X-thiophenes with primary and secondary amines in methanol
Consiglio G.
;Guernelli S.;
2002
Abstract
The kinetics of the reactions of some 2-L-5-nitro-3-X-thiophenes with primary and secondary amines in methanol at various temperatures have been studied with the aim of obtaining information about the proximity effects of 3-X ortho-like substituents. The results obtained have shown that for all the substituents considered, except for X = Br, the proximity effects of steric nature are of little relevance with respect to the electronic ones. Thus, it has been possible to establish a set of ortho sigma constants which account well for the electronic effects of 3-X substituents and to obtain excellent linear free energy ortho-correlations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
