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An improved scale of solvent nucleophilicity based on the solvolysis of the S-methyldibenzothiophenium ion

Dennis N. Kevill, +1 more
- 01 Mar 1991 - 
- Vol. 56, Iss: 5, pp 1845-1850
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This article is published in Journal of Organic Chemistry.The article was published on 1991-03-01. It has received 178 citations till now. The article focuses on the topics: Scale (ratio) & Solvolysis.

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Rate and product studies in the solvolyses of two arenesulfonic anhydrides

TL;DR: The specific rates of solvolysis of benzenesulfonic anhydride and p-toluenesulfonic a-hydride were measured conductometrically at -10°C in 34 solvents for 1 and 33 solvectors for 2 as discussed by the authors.
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Rate and Product Studies on the Solvolyses of Allyl Chloroformate

TL;DR: In this paper, the solvent kinetic isotope effect (SKIE, kMeOH/kMeOD) of 2.16 was also in accord with the SN2 mechanism, and the product selectivity (S) for the solvolyses of 3 in alcohol/water mixtures was 1.3 to 3.9, which was also consistent with the proposed bimolecular reaction mechanism.
Journal ArticleDOI

Kinetic Studies of the Solvolyses of Isopropenyl Chloroformate

TL;DR: In this paper, the aminolyses of acetyl chloride, MeCOCl, and methyl chloroformate, MeOC-OCl, have been proposed to proceed by rate-limiting breakdown of a zwitterionic tetrahedral intermediate, T
Journal ArticleDOI

Gas‐phase stability of tertiary carbenium ions and rates of solvolysis of tertiary derivatives

TL;DR: In this paper, the stability of tertiary carbenium ions was determined in the gas phase by ion cyclotron resonance (ICR) and by dissociative proton attachment (DPA).
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