Solvolysis of o-methylbenzenediazonium tetrafluoroborate in acidic methanol-water mixtures. Further evidence for nucleophilic attack on a solvent separated aryl cation
✍ Scribed by R. Pazo-Llorente; M. J. Sarabia-Rodriguez; E. Gonzalez-Romero; C. Bravo-Diaz
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 154 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0538-8066
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✦ Synopsis
Rate constants for dediazoniation product formation and arenediazonium ion loss and product yields of solvolysis of o-methylbenzenediazonium tetrafluoroborate in acidic methanol-water mixtures at T ϭ 35ЊC are reported. Observed rate constants for diazonium ion loss and product formation are the same, increasing about 45% ongoing from water to methanol, and are not affected by added electrolytes like HCl, NaCl, and CuCl 2 . Only three dediazoniation products are detected, o-cresol, o-chlorotoluene, and o-anisole. All data are consistent with a rate-determining step formation of an aryl cation that reacts immediately with available nucleophiles. The selectivity of the reaction toward nucleophiles, S, which can be