182805-17-0Relevant articles and documents
PARTICIPATION OF A NEIGHBORING AMIDE GROUP IN THE HYDROLYTIC C-OAr CLEAVAGE IN N-(ω-PHENOXYALKYL)AMIDES. PART II. N,N-BIS(2-PHENOXYETHYL)ACETAMIDE, N,N-BISACET- AND PROPIONAMIDES
Dobrzeniecka, Regina
, p. 515 - 523 (2007/10/02)
The hydrolysis rates of N,N-bis(2-phenoxyethyl)acetamide and the isomeric N,N-bisacet- and propionamides have been determined in a hydrochloric acid-dioxane solution in the range of 2.65-5.20 mole/dm3 at 94.6 deg C.In all cases the overall pseudo-first-order rate constant kobs = kA + kB, where kA is the rate constant for the formation of N,N-(bis(2-phenoxyethyl)amine A, while kB is the rate constant for the formation of 2-phenoxy-2'-hydroxydiethylamine B.It has been found that the alkyl group at the carbonyl carbon atom and the chlorine atom in the benzene ring have an influence on the overall rate of hydrolysis as well as on the proportion of products A and B.The values of the kB/kA ratio are higher in the case of propionamides, while the value of kB decreases in the following order para above ortho above meta for both series of the chloro substituted amides.