Isokinetic correlation analysis of the series of electrophilic substitution reactions of o-substituted phenylmercurials

被引:0
作者
Wang, YL [1 ]
Wu, YJ
机构
[1] Chinese Acad Sci, Inst Chem Met, Natl Key Lab Biochem Engn, Beijing 100080, Peoples R China
[2] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China
来源
SCIENCE IN CHINA SERIES B-CHEMISTRY | 2001年 / 44卷 / 02期
关键词
isokinetic correlation; dominant factor; electrophilic substitution; arylmercurials;
D O I
10.1007/BF02879536
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isokinetic relationships of the series of electrophilic substitution reactions of o-substituted phenylmercurials are studied, and the results show, for the first time! that isokinetic correlation analysis can reveal the dominant factor in the system of the reactions. The analysis of S(E)2 of o-substituted phenylmercuric chlorides indicates that the steric effect of o-substituents is the predominant factor when I-2 is used as electrophilic agent, however, the electronic effect of o-substituents would become the predominant factor when HCl is used as the electrophilic agent. In S(E)1 of o-substituted phenylmercuric chlorides, the results of the analysis display that the predominant factor is the field effects of o-substituents. The determination of predominant factors in those reactions would provide further scientific basis for those reaction mechanisms.
引用
收藏
页码:182 / 190
页数:9
相关论文
共 12 条
[1]  
BELETSKAYA IP, 1965, IAN SSSR KH, V2, P240
[2]  
Connors K. A, 1990, CHEM KINETICS STUDY, P368
[3]  
ISAACS NS, 1987, PHYSICAL ORGANIC CHE, P129
[4]   MERCURY IN ORGANIC-CHEMISTRY .11. SYNTHESIS OF SYMMETRICAL 1,3-DIENES AND BIARYLS VIA RHODIUM CATALYZED DIMERIZATION OF VINYLMERCURIALS AND ARYLMERCURIALS [J].
LAROCK, RC ;
BERNHARDT, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1680-1684
[5]   MERCURY IN ORGANIC-CHEMISTRY .21. METHYLATION OF ORGANOMERCURIALS VIA ORGANORHODIUM SPECIES [J].
LAROCK, RC ;
HERSHBERGER, SS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 225 (01) :31-41
[6]   MERCURY IN ORGANIC-CHEMISTRY .19. RHODIUM PROMOTED METHYLATION OF ORGANOMERCURIALS [J].
LAROCK, RC ;
HERSHBERGER, SS .
TETRAHEDRON LETTERS, 1981, 22 (26) :2443-2446
[7]   THE ENTHALPY-ENTROPY RELATIONSHIP AND ITS IMPLICATIONS FOR ORGANIC CHEMISTRY [J].
LEFFLER, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (09) :1202-1231
[8]  
PAN ZH, 1985, ACTA CHIM SINICA, V43, P801
[9]   KINETICS AND MECHANISM OF DIMERIZATION OF ARYLMERCURIALS [J].
WANG, YL .
INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1993, 25 (02) :91-96
[10]   Effects of ortho-substituents in protonolysis of arylmercuric chlorides with hydrochloric acid [J].
Wang, YL ;
Wu, YJ .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2000, 65 (01) :35-46