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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 10
BKCSDE 31(10)
October 20, 2010 

Single Electron Transfer (SET) Pathway: Nucleophilic Substitution Reaction of 4-Chloro-7-nitrobenzofurazan with Anilines in MeOH-MeCN Mixtures
Hojune Choi, Kiyull Yang*, Sang Gyeong Lee, Jong Pal Lee, In Sun Koo*
Single electron transfer (SET) pathway, SNAr-Ad.E mechanism, Structure-reactivity correlations, Hydrogen bond, Isodielectric solvents
A nucleophilic substitution reaction of 4-chloro-7-nitrobenzofurazan (NBF-Cl) with anilines in MeOH-MeCN mixtures was conducted at 25, 35, and 45 oC. Based on the higher βnuc values (1.0 - 1.6) of the reaction and a good correlation of the rate constants with the reduction potentials of the aniline nucleophiles, the present reaction was initiated by a single electron transfer (SET). After this step, the reaction proceeds through a transition state similar to the normal SNAr-Ad.E pathway.
2801 - 2805
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