Accession Number : AD0703098

Title :   THE SN MECHANISM IN AROMATIC COMPOUNDS. XXXVIII. COMPARATIVE REACTIVITY OF 1-HALOGENO-2,6-DINITROBENZENES AND SOME OTHER HALOGENONITROBENZENES,

Corporate Author : DEFENCE STANDARDS LABS MARIBYRNONG (AUSTRALIA)

Personal Author(s) : Biffin,M. E. C. ; Miller,J. ; Roper,R.

Report Date : 27 JUN 1969

Pagination or Media Count : 5

Abstract : The reactivity of 1-halogeno-2,6-dinitrobenzenes with methanolic methoxide has been studied quantitatively and compared with the results of similar studies of o- and p-halogenonitrobenzenes and 1-halogeno-2,4-dinitrobenzenes. Adverse steric interactions of the ortho-nitro group are very small in the o-halogenonitro- and 1-halogeno-2,4-dinitrobenzenes. The interactions are substantially larger in the reactions of 1-halogeno-2,6-dinitrobenzenes in displacement of Cl, Br, and I, but not of F, but they are small compared to steric interactions found in many other classes of reactions. Steric effects are observed as a reduction in rates affecting values of the Substituent Rate Factors of the o-nitro group, and affecting also the mobility as a leaving group of Cl, Br, and I, but not of F. (Author)

Descriptors :   (*NITROBENZENES, CHEMICAL REACTIONS), (*HALOGENATED HYDROCARBONS, NITROBENZENES), CHLORINE COMPOUNDS, FLUORINE COMPOUNDS, BROMINE COMPOUNDS, IODINE COMPOUNDS, AUSTRALIA

Subject Categories : Organic Chemistry
      Physical Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE