19759-89-8Relevant 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
Studies on the Thermal Isomerization of N-Arylmethylbenzotriazoles
Katritzky, Alan R.,Perumal, Subbu,Fan, Wei-Qiang
, p. 2059 - 2062 (2007/10/02)
The thermal isomerizations of N-benzyl-, N-diarylmethyl- and N-trityl-benzotriazole, and of N--, and N-trityl-5,6-dimethylbenzotriazole under nitrogen have been investigated.In all these cases , the N-1 isomer predominates over the N-2 isomer at thermodynamic equilibrium, to an extent which depends on the steric bulk of the N-substituent.The rate of attainment of equilibrium depends on the electronic effects of the substituents, both in the benzotriazole ring and in the migrating group.These results, in conjunction with a cross-over experiment, support a mechanism involving a heterolytic N-C bond cleavage followed by an intermolecular rearrangement.
