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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...
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

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Chlorine isotopes exist as 35Cl and 37Cl in a 3:1 ratio, while bromine isotopes exist as 79Br and 81Br in a 1:1 ratio. The mass spectrum of alkyl halides typically produces two distinct molecular ion peaks, the molecular ion peak, [M], and the molecular ion plus two, [M + 2] peak. The relative heights of these two peaks are proportional to the isotopic abundance ratios of the halide. For example, 2‐chloropropane and 1‐bromopropane display two peaks with relative peak heights in a 3:1 and...
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Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

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This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Updated: Feb 5, 2026

Identification of Novel CK2 Kinase Substrates Using a Versatile Biochemical Approach
11:11

Identification of Novel CK2 Kinase Substrates Using a Versatile Biochemical Approach

Published on: February 21, 2019

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Alquilo isósteros

Priyakumari Chakkingal Parambil1, Roald Hoffmann1

  • 1Department of Chemistry and Chemical Biology , Cornell University , 162 Sciences Drive , Ithaca , New York 14853 , United States.

Journal of the American Chemical Society
|September 12, 2018
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores sintetizaron nuevos isósteros de metilo zwitteriónicos reemplazando los átomos de carbono con elementos cargados específicos. Estos compuestos son isoelectrónicos a los alquilos y ofrecen nuevas posibilidades en la estabilización de sistemas aromáticos cargados.

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Área de la Ciencia:

  • * Química orgánica
  • * Química computacional
  • * Ciencias de los materiales

Sus antecedentes:

  • * Los isósteros de metilo son compuestos análogos a los alquilos, isoelectrónicos o de isovalencia electrónica.
  • * Las especies zwitteriónicas, que poseen cargas positivas y negativas, presentan propiedades químicas únicas y desafíos de estabilización.
  • * Estudios anteriores han explorado ciertos compuestos zwitteriónicos, pero se necesitan más ejemplos.

Objetivo del estudio:

  • * Construir nuevos isósteros de metilo zwitteriónicos utilizando elementos del grupo 13 y del grupo 15.
  • * Explorar estrategias para estabilizar estas especies formalmente zwitteriónicas.
  • * Extender el concepto a los isósteros de xileno dicationicos y dianiónicos.

Principales métodos:

  • * Diseño conceptual y construcción teórica de nuevas estructuras moleculares.
  • * Utilizando sustituyentes cargados (ER3- y E'R3+) para sustituir las unidades CR3 neutras.
  • * Centrándose en los sistemas de anillos de 3, 5, 7 y 8 miembros.

Principales resultados:

  • * Construcción teórica exitosa de varios nuevos isósteros de metilo zwitteriónicos.
  • * Demostró la viabilidad del uso de elementos cargados para crear análogos isoelectrónicos.
  • * Propuso una estrategia para los isósteros de xileno dicationicos y dianiónicos.

Conclusiones:

  • * Los isósteros de metilo zwitteriónicos pueden diseñarse y sintetizarse utilizando elementos cargados específicos.
  • * Estos compuestos ofrecen potencial para estabilizar sistemas aromáticos contracargados.
  • * La estrategia puede ampliarse para crear sistemas dicationic y dianionic relacionados.