1361954-46-2Relevant academic research and scientific papers
Nucleophilic reactivities of the anions of nucleobases and their subunits
Breugst, Martin,Corralbautista, Francisco,Mayr, Herbert
supporting information; experimental part, p. 127 - 137 (2012/03/09)
The kinetics of the reactions of different heterocyclic anions derived from imidazoles, purines, pyrimidines, and related compounds with benzhydrylium ions and structurally related quinone methides have been studied in DMSO and water. The second-order rate constants (logk2) correlated linearly with the electrophilicity parameters E of the electrophiles according to the correlation logk2 = sN(N+E) (H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957) allowing us to determine the nucleophilicity parameters N and sN for these anions. In DMSO, the reactivities of these heterocyclic anions vary by more than six orders of magnitude and are comparable to carbanions, amide and imide anions, or amines. The azole anions are generally four to five orders of magnitude more reactive than their conjugate acids. Copyright
