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Related Concept Videos

Resonance and Hybrid Structures02:16

Resonance and Hybrid Structures

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According to the theory of resonance, if two or more Lewis structures with the same arrangement of atoms can be written for a molecule, ion, or radical, the actual distribution of electrons is an average of that shown by the various Lewis structures.
Resonance Structures and Resonance Hybrids
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N–O and N=O bonds.
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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Lewis Acids and Bases

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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...
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Lewis Acids and Bases02:16

Lewis Acids and Bases

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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...
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VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

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Effect of Lone Pairs of Electrons on Molecule Geometry
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Resonance02:52

Resonance

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The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds.
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Related Experiment Video

Updated: Feb 18, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

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An Intramolecular Lewis Adduct with Diverse FLP Reactivity.

Hui Li1, Shaoying Ju1, Ting Chen1

  • 1Institute of Drug Discovery Technology and Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo 315211, Zhejiang, China.

Inorganic Chemistry
|February 16, 2026
PubMed
Summary

A stable intramolecular Lewis adduct was synthesized and demonstrated frustrated Lewis pair reactivity. This compound enables diverse chemical transformations, including additions, dimerizations, and cycloadditions.

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Supramolecular Chemistry

Background:

  • Intramolecular Lewis adducts offer unique reactivity profiles.
  • Frustrated Lewis pairs (FLPs) are Lewis acids and bases that cannot directly neutralize each other, leading to unique reactivity.
  • Designing stable FLP-type molecules is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To synthesize a stable intramolecular Lewis adduct.
  • To investigate the frustrated Lewis pair-type reactivity of the synthesized adduct.
  • To explore its utility in catalyzing diverse organic transformations.

Main Methods:

  • Hydroboration of 2-diphenylphosphinobenzaldehyde with HB(C6F5)2 to form the intramolecular Lewis adduct.
  • Reaction of the adduct with various unsaturated substrates like aldehydes, alkynes, azides, and isocyanides.
  • Full characterization of all isolated products using spectroscopic and analytical techniques.

Main Results:

  • A stable intramolecular Lewis adduct (1) was successfully prepared.
  • Compound 1 exhibited frustrated Lewis pair-type reactivity towards aldehydes, alkynes, azides, and isocyanides.
  • Diverse products were isolated, including aldehyde 1,2-addition derivatives (2-4), alkyne dimers (5-6), phosphinimine (7), isocyanide adducts (8-9), and a [4+2] cycloaddition product (10).

Conclusions:

  • The synthesized intramolecular Lewis adduct displays significant frustrated Lewis pair reactivity.
  • This reactivity enables a range of valuable organic transformations.
  • The study provides insights into the mechanism of these reactions and the potential of such adducts in synthesis.