Following our recently published work on the two-electron redox chemistry of p-nitro- and p-cyanobenzene diazohydroxides in mixed acetonitrile (AN) and phosphate buffer mixtures, 50:50% v/v, we have studied the reaction of hydroxide addition to a series of aryl substituted diazonium tetrafuoroborate salts in AN and or dimethyl sulfoxide (DMSO)-aqueous phosphate buffer mixtures. The rate of hydroxide addition to the electrophilic aryldiazonium ion is significantly catalyzed in the mixed solvent relative to 100% aqueous buffers. In addition to validating the Hammett structure-reactivity relationship, we will report on the role of anion desolvation in dipolar-aprotic solvents, polarity of the mixed solvent, and general-base catalysis in the formation of aryl diazohydroxides.

Role of dipolar-aprotic solvents in the addition reaction of hydroxide ion to aryldiazonium tetrafluoroborate salts

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.