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Lewis Acid/Base Interaction Matrix Database


Type 14 Lewis Acid/Base Complexation Chemistry

Friedel-Crafts Reagents
Bonding: Charge controlled ionic complexes are highly reactive (transient) species which are prepared in solution where they show little or no ion pairing.
Charge: The charge on a Type 14 complex is always neutral.
Chemistry:

Type 14 complexes include electrophilic haloenium ion or carbenium ion reagents with non-electrophilic counter ions.

Lobe-LUMO Lewis acids have a strong symbiotic affinity for halogen anion ligands, close in type to those they already possess. Thus:

•   AlCl3 has a high affinity for Cl to give [AlCl4]

•   FeBr3 has a high affinity for Br to give [FeBr4]

Type 14 complexes are not prepared from the cation plus anion, but from the dihalogen, organic halide or acyl halide plus halophilic Lewis acid:

Cl2        +      AlCl3      →        Cl+   [AlCl4]

R–Cl     +      AlCl3      →        R+    [AlCl4]

The resulting Type 14 complexes act as sources of "naked" electrophilic Cl+, Br+ and R3C+, etc. that are able to undergo electrophilic aromatic substitution with benzene and other aromatics:

Congeneric Series: Few series.
Type 14 Lewis acid/base complex (generic)
Acyl cation/tetrachloroaluminate complex (generic)

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Bromine tetrabromoferrate

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Carbenium ion/tetrachloro aluminate complex (generic)

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Chlorine perchlorate

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Chlorine tetrachloroaluminate

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N5 hexafluoroarsinate

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Nitronium tetrafluoroborate

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Xenon fluoride hexafluoroplatinate(V)

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