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Lewis Acid/Base Interaction Matrix Database


Type 13 Lewis Acid/Base Complexation Chemistry

Reduction of Lewis Acid
Bonding:

s-HOMO Lewis bases are reducing agents, so complexation with hydride or hydrogen is also classed as reduction.

However, with respect to carbenium ions and organic chemistry, as C-H bonds are polarised Cδ––Hδ+, ie as weak Brønsted acids, Type 13 complexes reverse their C-H bond polarisation:

C+ +   H    →   C–H    →   Cδ––Hδ+

and so become Type 3 complexes.

Charge: Complexes may be negatively charged or they may be neutral, or a reaction may occur.
Chemistry:

Carbenium ion (ie where the Lewis acid = R3C+ + hydride ion) complexation reactions are rare as both species interact strongly with their counter ions.

  • The true X + Y → X-Y complexation reaction would have to be performed under high vacuum vapor phase conditions with the reactive species generated by an experimentally exotic process such as laser induced dissociation.
  • Alkyl halides, such as 3-bromohexane, are readily reduced by H2 plus a catalyst, or by hydride ion donor reagents, as are carbonyl functions.
  • Proton abstraction may occur if there is an acidic proton present and a strongly basic hydride donor reagent is used.
  • A few C-H functions can act donors of hydride ion: aldehydes in the Cannizzaro reaction and isopropoxide ions during Meerwein-Ponndorf-Varley reduction.
Congeneric Series: Few series.
Type 13 Lewis acid/base complex (generic)
Acetaldehyde

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Aldehyde (generic)

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1° Alkoxide ion (generic)

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Alkoxy aluminium hydride ion (generic)

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Alkoxy borohydride ion (generic)

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Alkyl aluminium hydride ion (generic)

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Alkyl borohydride ion (generic)

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Alkyl, -CH2- (generic)

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Dialkoxyaluminium hydride ion (generic)

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Dialkoxyborohydride ion (generic)

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Dialkylaluminium hydride ion (generic)

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Dialkylborohydride ion (generic)

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Diborane

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Diisobutylaluminium hydride

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Ethoxide ion

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Hydrogen bromide

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Hydrogen chloride

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Hydrogen iodide

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Isopropyl alkoxide ion

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Methoxide ion

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Tetrahydroaluminate

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Tetrahydroborate ion

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Trialkoxyaluminium hydride ion (generic)

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Trialkoxyborohydride ion (generic)

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Trialkylaluminium hydride ion (generic)

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Trialkylborohydride ion (generic)

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