Ranking Lewis Acids: Weak to Strong - Resources & Tables

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Discussion Overview

The discussion revolves around the ranking of Lewis acids from weak to strong, focusing on their reactivity and the factors influencing their acidity. Participants seek resources, tables, and charts to clarify the ranking and properties of various Lewis acids.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant requests resources for ranking Lewis acids and expresses difficulty in finding clear information on their reactivity.
  • Another participant questions whether the original poster has conducted any prior research on the topic.
  • A participant shares insights from organic synthesis books, noting that the classification of Lewis acids as strong or weak is vague and lacks numerical evaluation.
  • Factors affecting Lewis acidity mentioned include the metal's unoccupied molecular orbitals, electronegativity of substituents, and the influence of bulky groups on acidity.
  • Hard/soft acid analysis is introduced, with examples provided, such as Iron(II) chloride being softer than Iron(III) chloride and Zinc(II) chloride being a stronger Lewis acid than Cadmium(II) chloride.
  • Some knowledge of electron affinity is suggested as relevant to understanding Lewis acids, emphasizing their role as electron acceptors.

Areas of Agreement / Disagreement

Participants do not reach a consensus on a specific ranking of Lewis acids, and multiple views on the factors influencing their acidity are presented.

Contextual Notes

The discussion highlights limitations in the clarity and numerical evaluation of Lewis acid strength, as well as the dependence on various factors such as substituent effects and the hard/soft acid concept.

endy
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Hello,
Just wondering if anyone could post some resources on lewis acids: ie weak to strong lewis acid ranking
or maybe some table or chart of lewis acids and their reactivity

I haven't been able to find any resources thus far regarding lewis acids and their reactivity rankings...

... thanks!
 
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Have you done any research on the problem?
 
well after checking out couple organic synthesis books... yes, and results aren't as clear cut as expected

I understand that the metal's unoccupied molecular orbitals and the electronegativity of its subsituents affect its ability to accept electrons but all the material I've read categorizes them as either strong or weak lewis acids (vague). There seems to be no numerical way of evaluating the acidity of a lewis acid. So i was wondering if anyone could give a general ranking.

These are what I might be interested in working with:
Comments on what would be more acidic than the other and why would be appreciated...
(To start off i know AlCl3 is a strong lewis acid, and what is typically used for F-C alkyl/acylations...)

Aluminum isopropoxide ≥98%
Aluminum chloride anhydrous
Aluminum bromide anhydrous

Boron trichloride
Boron trifluoride
Boron trifluoride tetrahydrofuran complex

Iron(III) chloride anhydrous,
Iron(III) bromide

Montmorillonite

Tin(IV) chloride

Titanium(IV) chloride

Titanium(IV) isopropoxide
 
You are actually asking several questions in one. Lewis acids are not usually ranked for strength like mineral acids are but many of the same principles apply. In general, electron withdrawing groups increase the acidity of the metal and electron releasing groups lower the acidity. If the substituted group is bulky and prevents close approach by the reacting species, effective acidity can be lowered. Hard/soft acid analysis is important. Hard acids are acids with high charge and small size while soft acids have lower charge and larger size. Iron(II) chloride is a softer acid than iron(III) chloride, for example. Zinc(II) chloride is a stronger Lewis acid than cadmium(II) chloride.
Since Lewis acids are electron acceptors, some knowledge of electron affinity is useful as well. Does that help?
 

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