Alkaline hydrolysis of 2-phenoxyquinoxaline in reactive counter-ion micelles: Effects of head group size

✍ Scribed by Angela Cuenca

• Book ID: 101249669
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 164 KB
• Volume: 30
• Category: Article
• ISSN: 0538-8066
• DOI: 10.1002/(sici)1097-4601(1998)30:11<777::aid-kin1>3.0.co;2-s

✦ Synopsis

The reaction of 2-phenoxyquinoxaline (1) with hydroxide ion is accelerated by reactive counter-ion micelles of cetyltrialkylammonium hydroxides ( Et, n-Pr, and alkyl ϭ Me, n-Bu), cetylmethylpiperidinium hydroxide, and cetylquinuclidinium hydroxide containing bulky head groups. First-order rate constants for reaction of (1) with OH Ϫ increase with increasing bulk of the head group and are associated with an increase in nucleophile reactivity as water is squeezed away from the micelle surface. Micellar effects upon the alkaline hydrolysis of compound (1) were analyzed by using a model that describes micelle-ion interactions in terms of Langmuir isotherms.