Naslov
How Fast Do RbondX Bonds Ionize? A Semiquantitative Approach

Autori
Denegri, Bernard ; Ofial, Armin ; Jurić, Sandra ; Streiter, Andre ; Kronja, Olga ; Mayr, Herbert

Izvornik
Chemistry - A European Journal (0947-6539) 12 (2006), 6; 1657-1666

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
carbocations • kinetics • nucleophilic substitution • reaction mechanisms • solvent effects

Sažetak
The correlation equation log k25 °C = sf(Nf + Ef), where sf and Nf are nucleofuge-specific parameters referring to leaving group/solvent combinations and Ef are electrofuge-specific parameters referring to the incipient carbocation R+, are used to predict ionization rate constants of alkyl derivatives RX. We show how to employ the Ef parameters of reference electrofuges and the sf and Nf parameters of reference nucleofuges reported in the preceding article for determining further sf, Nf, and Ef parameters. Since sf is usually close to 1.0, one comes to the semiquantitative rule that at 25 °C, compounds RX for which Nf + Ef>-2 will solvolyze with half-lives of less than a minute, while the solvolysis half-lives will exceed 1 month if Nf + Ef<-6.5.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA