PROTON-TRANSFER REACTIONS FROM N-H ACID TO VARIOUS N-BASES IN ACETONITRILE

Deprotonation of 1,8-bis(4-toluenesulphonamido)-2,4,5,7-tetranitronaphthalene (TSATNN) by three proton sponges, three cryptands and pentaisopropylguanidine (PiPG) have been studies by FTIR, H-1 NMR and kinetic methods. In the case of the proton sponges the products of the proton transfer reactions were cations and an anion with [N-H ... N](+) and [N-H ... N](-) homoconjugated intramolecular hydrogen bonds, respectively. The reaction of the cryptands or PiPG with TSATNN yielded an [N-H ... N](-) anion with a homoconjugated intramolecular hydrogen bond and the protonated N-bases. The kinetic parameters of these reactions in acetonitrile were explained by the structure of the transition state.