Reactions of ferrocenyl-stabilised carbocations with water: substituent, medium, salt, and solvent isotope effects on rates and equilibria
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 1267-1273
- https://doi.org/10.1039/p29790001267
Abstract
Rates and equilibrium constants have been measured for reactions of ferrocenylalkyl cations FcC(R)Ar,FcCAr2, and FcCH(CHCH)nFc (R = H, But, and 1 -adamantyl; Ar = Ph and p-methoxyphenyl; n= 0 and 1) with water in H2O and in H2O–MeCN in the absence and presence of mineral acid (HCl or H2SO4), and a HR Fc acidity function has been constructed for reactions in H2O–MeCN (H2SO4). The rates of water addition to the cations and of acid-promoted heterolysis of ferrocenylalkanols are sensitive to structural, steric, and conformational effects. Medium, salt, and solvent isotope effects on rates and equilibria are consistent with a carbocation-like transition state.Keywords
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