Lewis Acid/Base Interaction Matrix Database


Type 19 Lewis Acid/Base Complexation Chemistry
Nucleophilic Attack on π-Systems

Bonding: Complexation leads to normal covalent and/or polar-covalent bonding.
Charge: Complexes may be negatively charged, positively charged or they may be neutral.
Chemistry: Nucleophilic attack, usually in an ambidentate manner, upon the π-LUMO Lewis Acid. One way to form π-LUMO Lewis Acids is to have a nucleofugal leaving group attached to a pro- π-LUMO Lewis Acid. Proton abstracters remove H+ to form the corresponding π-system.
Congeneric Series:

A number of interacting congeneric series are known, for example, phenyl methane carbenium ion/halogen anion complexes:

Chloride and other halogen anion nucleofuges are more easily substituted by hydroxide ion nucleophiles as –NO2 electron withdrawing group (EWG) functions are added (ortho and para) to the Nfg:

Type 19 Lewis acid/base complex (generic)
Allyl alcohol

more here
Benzene diazonium ion

more here
Benzyl bromide

more here
Benzyl isocyanide

more here
Diazonium ion (generic)

more here
Triphenylmethyl chloride

more here


Interactions and reactions classified as:
Type 19 Lewis Acid/Base Complexation Chemistry
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Poster
Nucleophiles & Bases

© Mark R. Leach 1999-


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