An analysis of electrophilic aromatic substitution: a "complex approach"

被引:24
|
作者
Stamenkovic, Nikola [1 ]
Ulrih, Natasa Poklar [1 ]
Cerkovnik, Janez [2 ]
机构
[1] Univ Ljubljana, Biotech Fac, Dept Food Sci & Technol, Jamnikarjeva 101, Ljubljana 1000, Slovenia
[2] Univ Ljubljana, Fac Chem & Chem Technol, Dept Chem & Biochem, Vecna Pot 113, Ljubljana 1000, Slovenia
关键词
DENSITY-FUNCTIONAL THEORY; GAS-PHASE; REGIOSELECTIVE BROMINATION; ORGANIC-COMPOUNDS; RESPONSE KERNEL; ARENIUM IONS; PI-COMPLEX; BENZENE; SPECTROSCOPY; ARENES;
D O I
10.1039/d0cp05245k
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Electrophilic aromatic substitution (EAS) is one of the most widely researched transforms in synthetic organic chemistry. Numerous studies have been carried out to provide an understanding of the nature of its reactivity pattern. There is now a need for a concise and general, but detailed and up-to-date, overview. The basic principles behind EAS are essential to our understanding of what the mechanisms underlying EAS are. To date, textbook overviews of EAS have provided little information about the mechanistic pathways and chemical species involved. In this review, the aim is to gather and present the up-to-date information relating to reactivity in EAS, with the implication that some of the key concepts will be discussed in a scientifically concise manner. In addition, the information presented herein suggests certain new possibilities to advance EAS theory, with particular emphasis on the role of modern instrumental and theoretical techniques in EAS reactivity monitoring.
引用
收藏
页码:5051 / 5068
页数:18
相关论文
共 50 条
  • [22] ELECTROPHILIC - AROMATIC-SUBSTITUTION DISCOVERY LAB
    JARRET, RM
    NEW, J
    PATRAITIS, C
    JOURNAL OF CHEMICAL EDUCATION, 1995, 72 (05) : 457 - 459
  • [23] An ab initio study of electrophilic aromatic substitution
    Daniel Zerong Wang
    Andrew Streitwieser
    Theoretical Chemistry Accounts, 1999, 102 : 78 - 86
  • [24] ELECTROPHILIC AROMATIC-SUBSTITUTION OF POLY(METHYLPHENYLPHOSPHAZENE)
    IRIARTE, JM
    ISLAM, MS
    WOOD, CE
    WISIANNEILSON, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 199 - INOR
  • [25] ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS OF ARSABENZENE
    ASHE, AJ
    CHAN, WT
    SMITH, TW
    TABA, KM
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05): : 881 - 885
  • [26] ELECTROPHILIC AROMATIC-SUBSTITUTION REACTIONS OF ARSABENZENE
    ASHE, AJ
    CHAN, WT
    SMITH, TW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 115 - 115
  • [27] Origin of deactivation of chlorobenzene in aromatic electrophilic substitution
    Tomoda, S
    Takamatsu, K
    Iwaoka, M
    CHEMISTRY LETTERS, 1998, (07) : 581 - 582
  • [28] Role of dynamics in enzymatic electrophilic aromatic substitution
    Merz, Kenneth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [29] ELECTROPHILIC AROMATIC-SUBSTITUTION IN CYCLOPROPENIUM IONS
    CLARK, T
    WEISS, R
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10): : 1790 - 1794
  • [30] ELECTROPHILIC SUBSTITUTION OF POLYSTYRENE WITH AROMATIC ANHYDRIDES - COMMENT
    SHERRINGTON, DC
    AITKEN, D
    JOURNAL OF APPLIED POLYMER SCIENCE, 1983, 28 (07) : 2463 - 2463