Journal of the American Chemical Society

Mechanism of solvolysis of substituted benzoyl halides

BD Song, WP Jencks

Index: Song, Byeong Doo; Jencks, William P. Journal of the American Chemical Society, 1989 , vol. 111, # 22 p. 8470 - 8479

Full Text: HTML

Citation Number: 111

Abstract

Abstract: Most substituted benzoyl fluorides undergo hydrolysis in aqueous solution through an associative mechanism with p= 1.7, kHOH/kmD= 2.3 i 0.2, little dependence on the leaving group (kCl/kF= 1.2), and general-base catalysis by fluoride ion. There is an abrupt change to a dissociative mechanism through an acylium ion intermediate for the hydrolysis of p-(dimethy1amino) benzoyl and (in part) p-anisoyl fluorides, with p+ 5-1.2, kcl/kF= 106- ...

Related Articles:

Vinylic cations from solvolysis. 29. Solvolysis of 9-(. alpha.-bromoarylidene) anthrones as a probe to the reactivity-selectivity relationship in solvolysis reactions

[Rappoport, Zvi; Apeloig, Yitzhak; Greenblatt, Jeremy Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3837 - 3848]

Facile oxidative conversion of alcohols to esters using molecular iodine

[Mori, Naoshi; Togo, Hideo Tetrahedron, 2005 , vol. 61, # 24 p. 5915 - 5925]

Solvent polarity and organic reactivity in mixed solvents: Evidence using a reactive molecular probe to assess the role of preferential solvation in aqueous alcohols

[Bentley, T. William; Ebdon, David N.; Kim, Eun-Ju; In, Sun Koo Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1647 - 1653]

More Articles...