SEARCH FOR ACID CATALYSIS OF REACTION OF THIOPHENOXIDE ION WITY 2,4-DINITROFLUOROBENZENE

In five different kinds of systems designed to elicit evidence of acid catalysis of the reaction named in the title, no evidence of such catalysis has been found. No evidence was found either of general acid catalysis or of a thiophenol term in the rate law; the latter would appear if there were catalysis by the solvated proton. Inasmuch as the separation of fluoride ion from carbon is known to respond to catalysis by acids, we conclude that the first step of the intermediate complex mechanism is rate limiting for this reaction. This conclusion is contrary to one reached by other workers on the basis of thermochemical calculations. © 1969, American Chemical Society. All rights reserved.