191226-78-5Relevant academic research and scientific papers
15N NMR and FTIR studies of 2,4-dinitroanilines and their salts
Gierczyk,Leska,Nowak-Wydra,Schroeder,Wojciechowski,Bartl,Brzezinski
, p. 217 - 225 (2007/10/03)
Twenty-two 2,4-dinitroanilines were synthesised and their pK(a) values were determined. The 2,4-dinitroanilines and their protonated forms were studied by 15N NMR spectroscopy. The relations between the 15N NMR chemical shifts and the pK(a) values of the 2,4-dinitroanilines and their salts were found to be linear. The deprotonation reaction of N-methyl-2,4- dinitroanilines and N-methyl-2,4,6-trinitroaniline by MTBD was successful only for the latter and yielded protonated MTBD molecule and the anion in which the electrons are strongly delocalised. The kinetic parameters of the 2,4-dinitroanilines in reactions with hydroxide ions in mixed solvent DMSO:water (95:5, v/v) were determinated and discussed. (C) 2000 Elsevier Science B.V.
Kinetics and mechanism of reactions between 1-N-crown ether-2,4-dinitrobenzenes and alkali metal hydroxides
LESka, BogusLawa,Schroeder, Grzegorz,Gierczyk, BLazej
, p. 461 - 470 (2007/10/03)
The following macrocylic compounds: 1-N-12C4-2,4-dinitrobenzene, 1-N-15C5-2,4-dinitrobenzene and 1-N-18C6-2,4-dinitrobenzene were synthesized. Kinetics and spectroscopic studies of reactions between these compounds and alkali metal hydroxides (LiOH, NaOH, KOH, RbOH and CsOH) in mixed solvent DMSO water (95:5 v/v) were investigated. The results were compared to analogous reactions of 1-X-2,4-dinitrobenzenes. These studies show that the kinetics of the formation of both 3-hydroxy complex and phenolate ions depend strongly on the size of the cation. The formation of the stable complex of cations and 1-N-crown ether-2,4-dinitrobenzene increases the rate constant of formation of both 3-hydroxy complex and phenolate ions. The process of complex formation between the alkali metal cation and macrocylic compounds in mixed solvent DMSO : water is very fast and precedes the nucleophilic attack of hydroxide ion on the benzene ring.
