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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 9, Number 1
February 20, 1965 

Kinetic Studies of Chlorine Exchange between Benzyl Chloride and Radioactive Chloride Ion

Benzyl Chloride의 Chlorine 교환반응
Yong Ja Park, Ikchoon Lee

박용자, 이익춘
90% ethanol solution에서 benzyl chloride와 radioactive chloride(36Cl-)와의 exchange를 반응속도론적으로 연구하였으며 그 결과로 교환반응은 typical bimolecular reaction임을 알았고 그 activation parameter들은 각기 다음과 같았다. △H≠= 18.50 Kcal △S≠= -22.09 e.u. 특히 본실험 결과와 다른 실험결과를 종합토론함으로써 반응속도는 attacking anion의 nuclephilic ability에 크게 관계 됨을 입증할 수 있었으며 또한 exchange reaction에 있어서 halide들의 reactivity의 순서는 bond dissociation energy의 차로써 보다는 오히려 Swain의 nucleophilic parameter(n)로써 설명함이 더욱 타당함을 알았다.

Halogen exchanges between benzyl chloride and chloride ion have been studied in 90% ethanol-water mixture, and activation parameters in the exchange reaction have been determined; ΔH≠ = 18. 50 Kcal and ΔS≠ = -22. 09 e. u. Results indicated that the reaction proceeded via a typical bimolecular mechanism. The importance of nucleophilic ability of attacking anion in SN2 process has been stressed giving some experimental evidence. The order of reactivity of halides in the exchange reaction is better explained with the Swain's nucleophilic parameter than with the bond dissociation energies.

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