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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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Lewis Acids and Bases02:33

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

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

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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...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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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.
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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:
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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.
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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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Ácidos de Lewis de nitrógeno

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
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron nuevos ácidos de Lewis centrados en el nitrógeno, desafiando los conceptos químicos tradicionales. Estos nuevos ácidos de Lewis permiten la síntesis de triazanos cíclicos únicos, abriendo nuevas vías en la investigación química.

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Área de la Ciencia:

  • Química
  • Química orgánica
  • Ciencias de los materiales

Sus antecedentes:

  • Los ácidos de Lewis son cruciales en la síntesis química, por lo general con elementos distintos del nitrógeno como el átomo central.
  • El nitrógeno se reconoce convencionalmente como una base de Lewis, limitando su papel en la química del ácido de Lewis.

Objetivo del estudio:

  • Para reportar los primeros ácidos de Lewis robustos y modificables centrados en átomos de nitrógeno.
  • Explorar la síntesis y las propiedades de nuevos compuestos derivados de estos ácidos de Lewis de nitrógeno.

Principales métodos:

  • Síntesis de ácidos de Lewis centrados en el nitrógeno.
  • Caracterización de los aductos formados con bases de Lewis.
  • Preparación de triazanos cíclicos utilizando ácidos de Lewis de nitrógeno.
  • Cálculos teóricos para explicar la reactividad.

Principales resultados:

  • Demostró los primeros ácidos de Lewis estables con un átomo central de nitrógeno.
  • Se han preparado con éxito triazanas cíclicas con un motivo secuencial N-N-N.
  • Caracterizado aductos estables con varias bases de Lewis.
  • Los estudios teóricos aclararon la reactividad de estos ácidos N-Lewis.

Conclusiones:

  • El nitrógeno puede funcionar como un átomo central en los ácidos de Lewis robustos, expandiendo el alcance de la química del ácido de Lewis.
  • El desarrollo de ácidos de Lewis de nitrógeno proporciona una nueva ruta sintética para las triazanas cíclicas.
  • Estos hallazgos sugieren propiedades intrigantes y aplicaciones potenciales para los ácidos de Lewis de nitrógeno en varios dominios químicos.