Alkaline hydrolysis of n-ethyl-2,4-dinitroacetanilide

Journal Article · Fri Apr 23 04:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00348a035· OSTI ID:5261678

Skarzewski, J; Aoki, M; Sekiquchi, S

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), Journal Name: J. Org. Chem.; (United States) Vol. 47:9; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALINE HYDROLYSIS
AMINES
ANILINE
ANIONS
AROMATICS
BASES
CATALYTIC EFFECTS
CHARGED PARTICLES
CHEMICAL REACTIONS
DATA
DECOMPOSITION
EQUATIONS
EXPERIMENTAL DATA
HYDROLYSIS
INFORMATION
IONS
ISOTOPE EFFECTS
KINETICS
LYSIS
MEDIUM TEMPERATURE
NITRO COMPOUNDS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
REACTION KINETICS
SOLVOLYSIS
STEREOCHEMISTRY
THERMODYNAMIC ACTIVITY