354538-06-0Relevant articles and documents
A novel strategy for chromogenic chemosensors highly selective toward cyanide based on its reaction with 4-(2,4-dinitrobenzylideneamino)benzenes or 2,4-dinitrostilbenes
Heying, Renata S.,Nandi, Leandro G.,Bortoluzzi, Adailton J.,Machado, Vanderlei G.
, p. 1491 - 1499 (2015/02/19)
N-(2,4-dinitrobenzylidene)-4-methoxyaniline (1), 4-(N,N-dimethylamine)-N-(2,4-dinitrobenzylidene) aniline (2), 2,4-dinitro-4′-methoxystilbene (3), and 2,4-dinitro-4′-(dimethylamino)stilbene (4) were synthesized and studied in dimethyl sulfoxide in a novel strategy as anionic chromogenic chemosensors. The color of the solutions of these compounds changed only in the presence of cyanide. The kinetic studies were performed with compounds 1-3 in an excess of cyanide. Higher second-order rate constant values were obtained for the compounds containing a methoxy group in relation to the compounds with a dimethylamino substituent, since the methoxy group donates electronic density to the 2,4-dinitrophenyl electron-accepting group less easily compared with the dimethylamino group. Stilbenes generally have greater structural rigidity than imines, facilitating the action of the substituents through the mesomeric effect. The data obtained indicate that the anion acts as a nucleophile, being responsible for C=N bond breaking. The C=C bridge is not broken in the stilbene dyes, but cyanide performs a nucleophilic attack on the 2,4-dinitrophenyl group.
Precipitation-driven self-sorting of imines
Lirag, Rio Carlo,Osowska, Karolina,Miljanic, Ognjen S.
supporting information; experimental part, p. 4847 - 4850 (2012/07/14)
Judicious choice of precipitation conditions can lead to self-sorting of equilibrating mixtures of aromatic aldehydes and substituted anilines into a handful of imine products. The selectivity of this process is caused by the solubility differences among possible imines in the EtOH-H2O solvent mixtures used in precipitation.
