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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

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Benzene diazonium ion

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Benzyl bromide

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Benzyl isocyanide

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Diazonium ion (generic)

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Triphenylmethyl chloride

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