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Molecular Orbital Studies on Nucleophilic Reactivities of Phenethyl Chlorides
이억석,이익춘,Lee, Euk-Suk,Lee, Ik-Choon Korean Chemical Society 1972 대한화학회지 Vol.16 No.2
1-염화 및 2-염화 훼네틸의 친핵성 반응에 대하여 분자 궤도론적 방법을 적용하여 상대적인 반응성을 연구하였다. EHT 계산에 의한 Population Analysis로 부터 할로겐 교환반응의 상대 속도를 설명할 수 있음을 밝혔으며 친핵성이 적은 Nucleophile의 경우 상대반응성이 바뀐다는 사실도 결합형성 과정이 중요하다는 것으로 이론적인 해석이 가능함을 밝혔다. Nucleophilic reactivities of 1-and 2-phenethyl chlorides have been investigated MO-theoretically using the EHT method. It has been shown that results of population analysis are consistent with the experimental order of relative nucleophilic reactivities and furthermore the reversal of the reactivity order for the less reactive nucleophile, $I^-$, could also be explained satisfactorily.
Ethanol-Water 溶液內에서의 p-Nitrobenzyl Chloride의 Solvolysis
이억석,Lee, Euk-Suk 대한화학회 1966 대한화학회지 Vol.10 No.1
Ethanol-water mixture 內에서 일어나는 p-nitrobenzyl chloride의 solvolysis反應에 대한 熱力學的 parameter를 구하고 이 data를 ${\delta}_M{\Delta}H^{\neq} = a'Y + b{\delta}_M{\Delta}S^{\leq}$에 適用함으로써 反應常數 a'가 50% 이하의 alcohol solvent에서나 50% 이상의 solvent에서 같다는 것을 알 수 있었다. 즉 water-rich solvent에서나 alcohol-rich solvent에서나 solvolysis反應의 mechanism은 변함이 없다는 것을 알았다. The thermodynamic parameters for the solvolysis of the p-nitrobenzyl chloride which take place in the ethanol-water mixture media were determined. From the application of this data to the formula ${\delta}_M{\Delta}H^{\neq} = a'Y + b{\delta}_M{\Delta}S^{\leq}$ the following conclusion was obtained. The substrate constant a' for this reaction was not varied in the media which contain more than 50% alcohol and less than 50% alcohol. From this, it is clear that the mechanism of this reaction is the same both in the water-rich solvent and in the alcohol-rich solvent.
이억석,홍승연,전윤탁 경성대학교 1985 부산수산대학 논문집 Vol.6 No.2
The substitution reactions of methyl para-substituted benzenesulfonates with nucleophils such as methanol, pyridine and sodium methoxide in methanol at 30℃ were investigated by conductometry and spectrometry in order to understand the reactivityselectivity relationship. The Hammett plot of kinetic data showed ρ values of 1.29, 1.18, 1.04 for the nucleophilic substitution reaction with methanol, pyridine and methoxide, respectively. Taking ρvalues as a selectivity parameter of the nucleophiles and considering the results with a series of nucleophiles showing the increase of reactivity in that order, there seems to be an inverse relationship between reactivity and selectivity.