Alkaline hydrolysis of n-ethyl-2,4-dinitroacetanilide
The alkaline hydrolyses of anilides have been studied extensively, but those of anilides bearing ortho substituents seem to be a rather unexplored field. As was shown for p-nitroacetanilide (1), the reaction mechanism of the base-catalyzed hydrolyses of anilides with strongly electron-withdrawing substituents on the phenyl moiety differs somewhat from the general one. The difference is caused by higher acidity of leaving-group nitroanilines. The results obtained in the case of the alkaline hydrolysis of N-ethyl-2,4-dinitroacetanilide are expected to conform to the reaction mechanism proposed for all other anilides, but the rate-determining step may change for such sterically hindered derivatives. That this prediction is fulfilled will be developed in latter sections.
- Research Organization:
- Gunma Univ., Japan
- OSTI ID:
- 5261678
- Journal Information:
- J. Org. Chem.; (United States), Vol. 47:9
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
NITRO COMPOUNDS
ALKALINE HYDROLYSIS
ANILINE
ANIONS
BASES
CATALYTIC EFFECTS
EQUATIONS
EXPERIMENTAL DATA
ISOTOPE EFFECTS
MEDIUM TEMPERATURE
REACTION KINETICS
STEREOCHEMISTRY
THERMODYNAMIC ACTIVITY
AMINES
AROMATICS
CHARGED PARTICLES
CHEMICAL REACTIONS
DATA
DECOMPOSITION
HYDROLYSIS
INFORMATION
IONS
KINETICS
LYSIS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SOLVOLYSIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)