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황원자의 친핵성 치환반응(제15보) 메탄올 - 아세토니트릴 혼합용매계에서의 염화나프탈렌술포닐의 가용매 분해반응
이익춘,강한근,송호봉,이정균 충북대학교 건설기술연구소 1982 建設技術論文集 Vol.1 No.1
Heats of solution were measured calorimetrically for MeOH, MeCN, 1-NSC, 2-NSC in MeOH-MeCN mixtures. Kinetic studies for the methanolysls of 1-NSC. 2-NSC and BSC both in MeOH-MeCN and MeOH-C_6H_6 mixtures have been conducted. Heats of solution of all substrates were positive value in MeOH-MeCN mixtures. It has been shown that the number of free methanols increases by addition of acetonitrile in methanol. The methanolyais rates of studied substrates were faster in MeOH-MeCN mixtures than in MeOH-C_6H_6 mixtures. This shows that the solvation of transition state is major factor in determining reaction rates. It has been found that the rates increase in the order of electron donating ability of arylmethyl system, but there was peri-hydrogen effect for 1-NSC. The reaction was entropy-controlled.
메탄올-아세토니트릴 혼합용매에서 염화알칸술포닐과 아닐린의 친핵 치환반응에 대한 속도론적 연구
이익춘,강한근,이해황,Ikchoon Lee,Han Keun Kang,Hai Whang Lee 대한화학회 1985 대한화학회지 Vol.29 No.5
염화 알칸술포닐과 파라 치환된 아닐린간의 친핵성 치환반응을 메탄올-아세토니트릴 혼합용매하에서 연구하였다. 기질의 반응성, 친핵체의 치환기효과 및 용매효과로 부터 반응 메카니즘이 $S_N2$임을 알았다. i-PSC의 경우 메탄올 조성이 커짐에 따라 전이상태가 더 loose해 짐을 알았다. Nucleophilic substitution reactions between Alkanesulfonylchlorides and p-substituted anilines in methanol-acetonitrile mixture have been studied kinetically. Reactivities of substrates, substituent effects of nucleophile and solvent effects indicate that the studied reaction proceeds via $S_N2$. The kinetic results show that transition state of the reaction between i-PSC and anilines becomes looser as the composition of methanol increases.