31789-98-7Relevant academic research and scientific papers
REACTIONS OF IMIDIC ACID DERIVATIVES WITH NUCLEOPHILIC REAGENTS. KINETICS OF THE REACTION OF BENZIMIDOYL HALIDES WITH ARYLAMINES IN APROTIC MEDIA. THE EFFECT OF THE STRUCTURE OF THE SUBSTRATE
Litvinenko, L. M.,Mikhailov, V. A.,Drizhd, L. P.,Savelova, V. A.
, p. 163 - 167 (2007/10/02)
In the kinetics of the reaction of N-substituted benzimidoyl chlorides R1C6H4C(Cl)=NSO2C6H4R2 with 3-nitro-4-bromoaniline in acetonitrile at 25 deg C first order is observed in each of the reagents.The constants for the sensitivity of the rate of the bimolecular reaction to the effect of R1 and R2 are as follows: ρR1 0.87 +/- 0.07 and ρR2 0.73 +/- 0.06.The rate of the reaction of N-phenylsulfonylbenzimidoyl chloride with 3-nitroaniline decreases by a factor of 240 in the transition from acetonitrile to chlorobenzene.Substitution of the chlorine atom by fluorine in the substrate (R1 = R2 = H) leads to a substantial decrease (by more than two orders of magnitude) in its reactivity.Together, these and previously obtained data make it possible to give preference to a mechanism of biomolecular nucleophilic substitution with the formation of a polar tetrahedral intermediate product, which undergoes dissociation in the rate-determining stage.
REACTIONS OF IMIDIC ACID DERIVATIVES WITH NUCLEOPHILIC REAGENTS. KINETICS OF THE REACTION OF N-SUBSTITUTED BENZIMIDOYL CHLORIDES WITH ARYLAMIDES IN APROTIC MEDIA. THE EFFECT OF THE STRUCTURE OF THE AMINE
Litvinenko, L. M.,Mikhailov, V. A.,Drizhd, L. P.,Savelova, V. A.,Kryuchkova, E. N.
, p. 1139 - 1143 (2007/10/02)
The kinetics of the reaction of primary aromatic amines H2NC6H4X with N-substituted benzimidoyl chlorides C6H5C(Cl)=NR in acetonitrile (R = CH3; COC6H5, SO2C6H5) and dioxane (R = CH3) at 25 grad C were studied.The sensitivity of the rate of the processes to variation in the substituent X in the arylamine depends substantially on the electronic nature of the substituent R in the in the imidoyl chloride, but isoparametric effects are not observed.It is supposed that this is due to the realization of a mechanism of bimolecular nucleophilic substitution at the imidoyl carbon atom through various transition states, depending on the substituent R at C=N bond.
