Stereoelectronic and conformational effects in Meisenheimer complexes. Intrinsic reactivities of spiro vs. 1, 1-dimethoxy and 1-methoxy-1-phenoxy complexes

CF Bernasconi, KA Howard

Index: Bernasconi, Claude F.; Howard, Keith A. Journal of the American Chemical Society, 1982 , vol. 104, # 25 p. 7248 - 7257

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Abstract

Abstract: Rate and equilibrium constants of formation of spiro Meisenheimer complexes derived from 1-(2-hydroxyeth-oxy)-2, 6-dinitro-4-X-benzenes in aqueous solution are compared with those for 1, l-dimethoxy Meisenheimer complexes derived from 2, 6-dinitro-4- X-anisoles. Hammett p values for the equilibrium constants are 8.2 for the dimethoxy and 5.9 for the spiro complexes, while the normalized p values for the rate constants of complex ...