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Acids, Bases and Neutralization Reactions03:26

Acids, Bases and Neutralization Reactions

An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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.
Acids, Bases and Neutralization Reactions01:27

Acids, Bases and Neutralization Reactions

Acids and bases play several important roles in biology. The pH of a biological system can significantly impact the function of biological molecules, including enzymes, proteins, and nucleic acids. For example, enzymes have optimal pH ranges for their activity, and changes in pH can denature or alter their structure, affecting their function. Acids and bases also play a crucial role in cellular signaling and communication. The pH of the extracellular fluid around cells can influence the...
Production of Organic Acids01:25

Production of Organic Acids

Lactic acid, an important organic acid extensively applied in food, pharmaceutical, and biodegradable polymer industries, is primarily produced via microbial fermentation. This method is favored over chemical synthesis due to its environmental sustainability and capacity for enantiomerically pure product formation. Among various microbial processes, the fermentation of starch-based substrates stands out due to the abundance and renewability of raw materials like corn and potatoes.Hydrolysis of...

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Updated: Jul 13, 2026

Two-way Valorization of Blast Furnace Slag: Synthesis of Precipitated Calcium Carbonate and Zeolitic Heavy Metal Adsorbent
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Hidroboración con borano de piridina a temperatura ambiente con hidroboración con borano de piridina a temperatura

Julia M Clay1, Edwin Vedejs

  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Journal of the American Chemical Society
|April 21, 2005
PubMed
Resumen

Nuevos complejos de piridina borano activan alquenos para la hidroboración a temperatura ambiente. Este método ofrece una formación selectiva de monoaducto y una fácil conversión en sales útiles de alquiltrifluoroborato de potasio.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química del organoborón Química del organoborón

Sus antecedentes:

  • El borano de piridina (Py.BH3) es un reactivo utilizado en la síntesis orgánica.
  • La hidroboración es una reacción clave para la funcionalización de los alquenos.

Objetivo del estudio:

  • Desarrollar complejos activados de piridina borano para una hidroboración eficiente.
  • Para investigar el mecanismo de esta nueva reacción de hidroboración.
  • Para sintetizar las sales de alquiltrifluoroborato de potasio de los productos de hidroboración.

Principales métodos:

  • Tratamiento del borano de piridina con yodo, bromo o ácidos fuertes para formar complejos Py.BH2X.
  • Reacción de los complejos Py.BH2X con alquenos para la hidroboración.
  • Conversión de los productos de hidroboración en sales de alquiltrifluoroborato de potasio utilizando KHF2.2. metanol.

Principales resultados:

  • Los complejos Py.BH2X activados efectivamente hidroboran alquenos a temperatura ambiente.
  • La evidencia sugiere un inusual mecanismo de hidroboración que involucra el desplazamiento de grupos.
  • Py.BH2I selectivamente produce monoadductos, a diferencia de THF.BH3.
  • Los productos crudos se convierten fácilmente en sales de alquiltrifluoroborato de potasio.

Conclusiones:

  • Los complejos activados de piridina borano ofrecen un método versátil y selectivo para la hidroboración de alquenos.
  • La reacción se produce a través de un mecanismo único.
  • Las sales de trifluoroborato resultantes son valiosos intermediarios sintéticos.