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Videos de Conceptos Relacionados

Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
16.6K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
2.1K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

7.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
7.3K
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

2.2K
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
2.2K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.0K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

3.4K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
3.4K

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

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Una nueva herramienta para guiar las reacciones de halofuncionalización: la escala de afinidad al halenio (HalA).

Kumar Dilip Ashtekar1, Nastaran Salehi Marzijarani, Arvind Jaganathan

  • 1Engineering and Process Sciences, The Dow Chemical Company , Midland, Michigan 48674, United States.

Journal of the American Chemical Society
|August 26, 2014
PubMed
Resumen

Introducimos HalA, una nueva escala que mide la afinidad de iones de halenio, para predecir la selectividad de la reacción. Esta herramienta cuantifica las fuerzas de enlace, ayudando en el descubrimiento de nuevas reacciones químicas.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química computacional es la química computacional.

Sus antecedentes:

  • Predecir la quimioselectividad en reacciones con múltiples sitios nucleófilos es un desafío.
  • Los métodos existentes a menudo se basan en la intuición química cualitativa, que puede ser insuficiente para sistemas complejos.

Objetivo del estudio:

  • Introducir un nuevo descriptor cuantitativo, la afinidad al halenio (HalA), para evaluar las fuerzas de enlace del grupo funcional a los iones de halenio.
  • Desarrollar una herramienta predictiva para la quimioselectividad en reacciones de halofuncionalización.

Principales métodos:

  • Desarrollo de la escala HalA para clasificar los posibles aceptores de iones de halenio.
  • Clasificación de varias bases de Lewis, incluidos alquenos, aminas, amidas, carbonilos y éteres, en la escala HalA.
  • Utilizando cálculos HalA para tener en cuenta intrínsecamente los efectos electrónicos, estéricos, anquiméricos y estereoelectrónicos.

Principales resultados:

  • La escala HalA proporciona una medida cuantitativa de la estabilización de iones de halenio por diferentes grupos funcionales.
  • Los alquenos, aminas, amidas, carbonilos y éteres han sido clasificados con éxito.
  • Los cálculos HalA ofrecen evaluaciones cuantitativas que van más allá de la intuición química tradicional.

Conclusiones:

  • La escala HalA permite una predicción rápida y directa de la quimioselectividad en sistemas de reacción complejos.
  • Este enfoque teórico-experimental facilita la predicción e identificación de nuevas reacciones químicas.
  • HalA sirve como una herramienta valiosa para comprender y controlar la reactividad en la halofuncionalización.