125253-84-1Relevant articles and documents
1-Acceptor Substituted Vinamidinium Salts: Stability and Reactivity
Bacher, Erwin,Gompper, Rudolf,Mertz, Ronald,Wagner, Hans-Ulrich
, p. 839 - 850 (2007/10/02)
1-Chloro- and 1,3-dichloro-vinamidinium salts react with potassium cyanide to afford 1-cyano- and 1,3-dicyano-vinamidinium salts.The former add nucleophiles at the C-3 position.MNDO calculations, competitive hydrolysis experiments and cyclic voltammetry reveal the following sequence of stabilities of vinamidinium salts: 1,3-(NMe2)2 > 1-NMe2 > 2-Aza > H > 2-(p-MeOC6H4) > 2-OMe > 2-Cl > 2-CN > 1,3-(SMe)2 > 1-Cl > 1-CO2Et > 2-NO2 > 1-CN > 1,3-(CN)2.Interestingly enough, reduction potentials show that 1,3-dicyanovinamidinium salt is more stable than a 1,3-dichlorovinamidinium salt, whereas a 1-chlorovinamidinium salt is more stable than a 1-cyanovinamidinium salt. - Keywords: Vinamidinium Salts, Hydrolysis, Cyclovoltammetry, MNDO Calculations