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Related Concept Videos

Lewis Acids and Bases02:16

Lewis Acids and Bases

17.8K
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...
17.8K
Lewis Acids and Bases02:33

Lewis Acids and Bases

48.9K
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...
48.9K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

4.0K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
4.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

5.1K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
5.1K
Exceptions to the Octet Rule02:55

Exceptions to the Octet Rule

38.2K
Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
38.2K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.6K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
5.6K

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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

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Nitrogen Lewis Acids.

Alla Pogoreltsev1, Yuri Tulchinsky1, Natalia Fridman1

  • 1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology , Technion City, Haifa 32000, Israel.

Journal of the American Chemical Society
|February 28, 2017
PubMed
Summary
This summary is machine-generated.

Researchers developed novel nitrogen-centered Lewis acids, challenging traditional chemical concepts. These new Lewis acids enable the synthesis of unique cyclic triazanes, opening new avenues in chemical research.

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Area of Science:

  • Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Lewis acids are crucial in chemical synthesis, typically featuring elements other than nitrogen as the central atom.
  • Nitrogen is conventionally recognized as a Lewis base, limiting its role in Lewis acid chemistry.

Purpose of the Study:

  • To report the first robust and modifiable Lewis acids centered on nitrogen atoms.
  • To explore the synthesis and properties of novel compounds derived from these nitrogen Lewis acids.

Main Methods:

  • Synthesis of nitrogen-centered Lewis acids.
  • Characterization of adducts formed with Lewis bases.
  • Preparation of cyclic triazanes using nitrogen Lewis acids.
  • Theoretical calculations to explain reactivity.

Main Results:

  • Demonstrated the first stable Lewis acids with a nitrogen central atom.
  • Successfully prepared cyclic triazanes featuring a sequential N-N-N motif.
  • Characterized stable adducts with various Lewis bases.
  • Theoretical studies elucidated the reactivity of these N-Lewis acids.

Conclusions:

  • Nitrogen can function as a central atom in robust Lewis acids, expanding the scope of Lewis acid chemistry.
  • The development of nitrogen Lewis acids provides a new synthetic route to cyclic triazanes.
  • These findings suggest intriguing properties and potential applications for nitrogen Lewis acids in various chemical domains.