Lewis Acid/Base Interaction Matrix Database


Type 16 Lewis Acid/Base Complexation Chemistry
Electrophilic Addition and SEAr Reactivity

Bonding: Halogen/alkene Type 16 complexes exhibit extensive back-bonding.
Charge: Positively charged complex, such as the bromonium ion, or some reaction pathway may yield products with a variety of charges.
Chemistry:

Classical Organic Chemistry

Many vacant p orbital Lobe-LUMO Lewis acids, particularly carbenium ions and acylium ions, are aggressive electrophiles, E+, able to react with π-HOMO organics, such as alkenes, via electrophilic addition or electrophilic addition-followed-by-elimination. For example:

An electrophile, E+, may react with benzene and other aromatics to give (Friedel-Crafts or nitration) electrophilic aromatic substitution products:

Congeneric Series:

Few congeneric series or planars of interest.

Type 16 Lewis acid/base complex (generic)
Benzoate ion

more here
Benzophenone

more here
Benzyl bromide

more here
Cyclopropane (generic)

more here
(+/-) trans 1,2-Dibromocyclohexane

more here
trans 1,2-Dichloroalkene (generic)

more here
(+/-) trans 1,2-Dichlorocyclohexane

more here
Disiamylborane

more here
gem-Dichloride (generic)

more here
1,1,2,2- Tetrachloroalkane (generic)

more here
Triphenylmethyl chloride

more here


Interactions and reactions classified as:
Type 16 Lewis Acid/Base Complexation Chemistry
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +1 1
      1 +4 2
      1 +1 1
      1 +1 1
       +
      1 +1 1
       + +
      1 +1 1
      1 +1 +1 1 +1 +1



Poster
Nucleophiles & Bases

© Mark R. Leach 1999-


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