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Related Concept Videos

Lewis Acids and Bases02:33

Lewis Acids and Bases

43.5K
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 Symbols and the Octet Rule02:36

Lewis Symbols and the Octet Rule

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Chemical bonds are complex interactions between two or more atoms or ions, which reduce the potential energy of the molecule. Gilbert N. Lewis developed a model called the Lewis model that simplified the depiction of chemical bond formation and provided straightforward explanations for the chemical bonds seen in most common compounds.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.6K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
2.6K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

2.7K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
2.7K
Resonance and Hybrid Structures02:16

Resonance and Hybrid Structures

16.5K
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.
16.5K
Lewis Structures and Formal Charges02:19

Lewis Structures and Formal Charges

14.0K
Lewis symbols can be used to indicate the formation of covalent bonds, which are shown in Lewis structures—drawings that describe the bonding in molecules and polyatomic ions. The periodic table can be used to predict the number of valence electrons in an atom and the number of bonds that will be formed to reach an octet. Group 18 elements, such as argon and helium, have filled electron configurations and thus rarely participate in chemical bonding. However, atoms from group 17, such as...
14.0K

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Updated: Jun 7, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Lewis-Acid Mediated Reactivity in Single-Molecule Junctions.

Jazmine Prana1, Leopold Kim1, Thomas M Czyszczon-Burton1

  • 1Department of Chemistry, University of Southern California, Los Angeles, California 90089, United States.

Journal of the American Chemical Society
|November 19, 2024
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Summary

This study reveals how molecule structure and gold electrodes influence chemical reactions at the nanoscale. Understanding these interfacial reactions is key for developing new molecular electronics and sensors.

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Single-Molecule Imaging of Lateral Mobility and Ion Channel Activity in Lipid Bilayers using Total Internal Reflection Fluorescence TIRF Microscopy
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Area of Science:

  • Nanotechnology
  • Surface Chemistry
  • Molecular Electronics

Background:

  • Chemical reactions at gold electrodes are typically monitored by molecular conductance.
  • The intrinsic properties of nanostructured interfaces play crucial, yet often misunderstood, roles.

Purpose of the Study:

  • To evaluate the intrinsic properties of nanostructured interfaces in single-molecule junctions.
  • To investigate the influence of linker chemical structure and electrode properties on interfacial reactions.

Main Methods:

  • Formation of single-molecule junctions using 4,4'-biphenyl backbones with 12 sulfur-based linkers.
  • Analysis of in situ bond breaking and forming reactions.
  • Systematic study of thioether components with varying substituents.
  • First-principles calculations to model electronic coupling.

Main Results:

  • Observed in situ S-C(sp3) bond breaking and C(sp2)-C(sp3) bond forming reactions.
  • Demonstrated the limits of substituent influence on conductance in physisorbed junctions.
  • Showed that bulky substituents decrease junction conductance by reducing electronic coupling.

Conclusions:

  • Linker chemical structure and electrode Lewis character significantly mediate interfacial reactions in break-junction experiments.
  • Bulky substituents on sulfur linkers decrease conductance and alter junction formation.
  • Findings rationalize the behavior of molecular junctions and inform future molecular electronics design.