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An estimate of steric influence on nucleophilic solvent assistance in secondary solvolysis.

✍ Scribed by Addy Pross; Rodi Koren

Book ID: 104234931
Publisher: Elsevier Science
Year: 1974
Tongue: French
Weight: 193 KB
Volume: 15
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82601-0

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✦ Synopsis

Nordlander' has recently evaluated expression (i) for a number of solvents, where k pinOTs and kg adOTs are the solvolytic rate constants for pinacolyl tosylate and Z-adamantyl tosylate respectively in those solvents and interpreted the data in terms of ion-pair return in the solvolysis of 2-adamantyl derivatives. This conclusion was based on the assumption that both 2-adamantyl and pinacolyl tosylates undergo idealized kc reaction.

2.3 Furthermore, it was assumed that in pinacolyl tosylate, methyl migration pre-empted ion-pair return and therefore, that deviations of expression (i) from a value of 1 reflected the degree of ion-pair return in 2-adamantyl tosylate in the particular solvent.

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## Abstract Kinetic studies are reported for the reactions with aniline in benzene of a series of X‐phenyl 2,4,6‐trinitrophenyl ethers [X = H; 2‐, 3‐, 4‐CH~3~; 2,4‐, or 2,6‐(CH~3~)~2~] a–f, and the results compared with those of the corresponding nitro derivatives. In the methyl series, kinetic dat