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Lewis Acids and Bases

Lewis Acids and Bases

In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...

Lewis Acids and Bases

Lewis Acids and Bases

This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...

α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the strong interaction...

Catalysis

Catalysis

Catalysis influences the rate of chemical reactions by providing an alternative reaction pathway with lower activation energy. A catalyst speeds up a reaction, but it is not consumed during the process. The fundamental principle of catalysis is the ability of a catalyst to alter the reaction mechanism, often introducing a more efficient pathway than the uncatalyzed process.In a catalyzed reaction, the catalyst participates directly in the reaction mechanism. It interacts with reactants to form...

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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Correction to "The Atroposelective Iodination of 2-Amino-6-arylpyridines Catalyzed by Chiral Disulfonimides Actually Proceeds via Brønsted Base Catalysis: A Combined Experimental, Computational, and Machine-Learning Study".

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Related Experiment Video

Updated: Jul 7, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

Lewis base catalysis in organic synthesis.

Scott E Denmark¹, Gregory L Beutner

¹Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA. denmark@scs.uiuc.edu

Angewandte Chemie (International Ed. in English)

|February 1, 2008

Summary

Gilbert Newton Lewis

Area of Science:

Organic Chemistry
Chemical Bonding Theory

Background:

Gilbert Newton Lewis's foundational concepts of donor-acceptor bonding.
The traditional understanding of acids and bases, including Brønsted acids.

Purpose of the Study:

To explore the growing recognition of Lewis bases as catalysts in chemical reactions.
To highlight the versatile catalytic capabilities of Lewis bases beyond their role as electronic complements to Lewis acids.

Main Methods:

Review of historical chemical bonding concepts.
Analysis of recent advancements in understanding Lewis base catalysis.

Main Results:

Lewis bases enhance both electrophilic and nucleophilic character in bound molecules.
Lewis bases exhibit remarkable versatility as catalysts.

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Last Updated: Jul 7, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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Published on: February 20, 2020

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Conclusions:

The catalytic role of Lewis bases is a significant and evolving area in organic chemistry.
Lewis bases offer diverse reactivity patterns for promoting chemical transformations.