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The Mechanism of the Acid-catalysed Hydrolysis of 1-Aryl-2,2,2-trifluorodiazoethanes

✍ Scribed by Georges Diderich

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
569 KB
Volume
55
Category
Article
ISSN
0018-019X

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✦ Synopsis

Szinzmavy. The rates of the acid-catalysetl hydrolysis < I f a serics of hryi-2,2,2-trifluorocliazocthanes Ia-d havc been mcasured in dioxan/\vatcr/HC104. Thc results arc well corrclatetl with the Hanznzett equation when up substituent constants are used ( @ = -1.74 and er, = -1.75).

Kinetic solvent isotope effccts, about 2.1, and general acid catalysis indicate that proton transfer is rate-determining ( A -S E ~ mechanism). Rate measurements havc also been made a t prcssures up t o 1400 atni. The cvaluatcd activation volumes, about -20 cm3/molc, indicate that a t least onc water molecule is bound in thc transition state of protonation. Katc measurements at low water conccntrations indicatc that no apparent change in mechanism has occurcd.

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