Vinyl cations. Part 13. Secondary kinetic deuterium isotope effects in the solvolysis of ring-substituted β-styryl trifluoromethanesulphonates
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1486-1490
- https://doi.org/10.1039/p29770001486
Abstract
The β-kinetic deuterium isotope effects have been measured in the solvolysis of a series of ring-substituted β-styryl trifluoromethanesulphonates. At 75 °C in aqueous 80% ethanol for the parent compound, kH/kD= 1.45; for p-Cl, kH/kD= 1.74; for m-Cl, kH/kD= 1.61; for p-CF3, kH/kD= 1.64; for p-NO2, kH/kD= 1.71. Both the protio- and deuterio-series gave an excellent Hammett correlation with σ+(ρ–4.12 and –4.17, respectively). The products of solvolysis were the corresponding acetophenones and phenylacetylenes. The significance of these results is discussed.Keywords
This publication has 0 references indexed in Scilit: