110210-11-2Relevant articles and documents
Studies of Tertiary Amine Oxides. Part 13. Solvent Effects on the Rate of Thermal Rearrangement of N-(2,4-Dinitrophenyl)piperidine N-Oxide
Khuthier, Abdul-Hussain,Hanna, Salim Y.,Al-Mallah, Khawla Y.
, p. 1157 - 1160 (1988)
The rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide was studied in ten aprotic solvents.Different correlations of the first-order rate coefficients (kobs.) with several solvent parameters were examined for the ten solvents with a range of 45 units in dielectric constant; the multiparameter equations of Krygowski and Fawcett, Koppel and Palm, and Kamlet and Taft were all examined.The kobs. values were correlated reasonably well with the Lewis basicity of the solvent, Gutmann's donor number, and Dimroth's ET(30) parameter when hydrogen-bond-donor solvents were excluded.
Studies of Tertiary Amine Oxides. Part 14. Protic Solvent Effects on the Rate of Thermal Rearrangement of N-(2,4-Dinitrophenyl)piperidine N-oxide
Al-Kazzaz, Abdul-Khalik S.,Hanna, Salim Y.,Khuthier, Abdul-Hussain
, p. 1661 - 1664 (2007/10/02)
The rate of rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide has been studied in 15 hydroxylic solvents.The first-order rate coefficients (kobs) have been successfully correlated with different solvent parameters.The results are explained in terms of the nucleophilic solvation capability of the solvent which in turn supports the previously proposed three-membered ring-activated complex.Moreover, the role of the HBD ability of the solvent in this reaction is also pronounced, particularly since reaction in alcohols exhibits lower reactivity and higher enthalpy and entropy of activation compared with aprotic solvents.