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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 11
BKCSDE 31(11)
November 20, 2010 

Kinetics and Mechanism of Nucleophilic Substitution Reaction of 4-Substituted-2,6-dinitrochlorobenzene with Benzylamines in MeOH-MeCN Mixtures
Young Sun Kim, Hojune Choi, Kiyull Yang*, Jong Keun Park, In Sun Koo*
Hydrogen bond, Isodielectric solvents, SNAr-Ad.E mechanism
The reaction rates of 4-X-2,6-dinitrochlorobenzenes (X = NO2, CN, CF3) with Y-substituted benzylamines (Y = p-OCH3, p-CH3, H, p-Cl) in MeOH-MeCN mixtures were measured by conductometry at 25 oC. It was observed that the rate constant increased in the order of X = NO2 > CN > CF3 and in the order of Y = p-OCH3 > p-CH3 > H > p-Cl. When the solvent composition was varied, the rate constant increased in the order of 100% MeOH < 50% (v/v) MeOH-MeCN < 100% MeCN. These results may be ascribed to the formation of hydrogen bonds between the alcoholic hydrogen and nitrogen of benzylamines in groud state (GS). We conclude that the reaction takes place via SNAr base on the transition state parameters ρX, ρY, βnuc, and solvent effects.
3279 - 3282
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