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Videos de Conceptos Relacionados

Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Preparation of Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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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...
3.3K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.7K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Arina heterocíclica de tipo nitrilio

Marisol Alvarado1, Lauren Tran1, Christina Tönshoff2

  • 1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.

Journal of the American Chemical Society
|June 2, 2025
PubMed
Resumen

Los investigadores informan de la primera síntesis de una N-hetarina de tipo nitrilio, una 1,6-BN-arina, que permite nuevas reacciones y acceso a nuevas estructuras de 1,2-azaborina.

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Área de la Ciencia:

  • Química orgánica
  • Química Heterocíclica
  • Metodología sintética

Sus antecedentes:

  • Las N-hetarinas son reactivos intermedios cruciales para la síntesis de compuestos heterocíclicos.
  • Las síntesis anteriores de N-hetarinas eran limitadas, lo que dificultaba el acceso a diversas estructuras.

Objetivo del estudio:

  • Para lograr la primera síntesis en la fase de solución de una N-hetarina de tipo nitrilio.
  • Explorar la reactividad y la utilidad sintética de este nuevo intermedio.

Principales métodos:

  • Síntesis en la fase de solución del 1,6-BN-arino derivado de la 1,2-azaborina.
  • Caracterización de la 1,6-BN-arina bajo condiciones de aislamiento de matriz.
  • Cálculos de la Teoría Funcional de Densidad (DFT) para aclarar la estructura electrónica.

Principales resultados:

  • El 1,6-BN-arine (2) fue sintetizado y caracterizado con éxito.
  • Demostró reactividad en las cicloadiciones [4+2], [3+2] y [2+2] y en la sustitución aromática electrofílica (EAS).
  • Las regioselectividades y las diastereoselectividades fueron consistentes con una especie polarizada de aryno/nitrilio.

Conclusiones:

  • El 1,6-BN-arine existe en resonancia entre las formas de ketenimine y nitrilium.
  • Este versátil bloque de construcción proporciona acceso a las 1,2-azaborinas funcionalizadas anteriormente inaccesibles.