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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

20.1K
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...
20.1K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.2K
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.
12.2K
Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

1.6K
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...
1.6K
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

8.5K
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...
8.5K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

10.1K
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...
10.1K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

3.0K
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.
3.0K

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

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Alkyl Isosteres.

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
Summary
This summary is machine-generated.

Researchers synthesized novel zwitterionic methyl isosteres by replacing carbon atoms with specific charged elements. These compounds are isoelectronic to alkyls and offer new possibilities in stabilizing charged aromatic systems.

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Area of Science:

  • * Organic Chemistry
  • * Computational Chemistry
  • * Materials Science

Background:

  • * Methyl isosteres are compounds analogous to alkyls, isoelectronic or iso-valence-electronic.
  • * Zwitterionic species, possessing both positive and negative charges, present unique chemical properties and stabilization challenges.
  • * Previous studies have explored certain zwitterionic compounds, but further examples are needed.

Purpose of the Study:

  • * To construct novel zwitterionic methyl isosteres using Group 13 and Group 15 elements.
  • * To explore strategies for stabilizing these formally zwitterionic species.
  • * To extend the concept to dicationic and dianionic xylene isosteres.

Main Methods:

  • * Conceptual design and theoretical construction of novel molecular structures.
  • * Utilizing charged substituents (ER3- and E'R3+) to replace neutral CR3 units.
  • * Focusing on 3-, 5-, 7-, and 8-membered ring systems.

Main Results:

  • * Successful theoretical construction of several new zwitterionic methyl isosteres.
  • * Demonstrated the viability of using charged elements to create isoelectronic analogs.
  • * Proposed a strategy for dicationic and dianionic xylene isosteres.

Conclusions:

  • * Zwitterionic methyl isosteres can be designed and synthesized using specific charged elements.
  • * These compounds offer potential for stabilizing countercharged aromatic systems.
  • * The strategy can be extended to create related dicationic and dianionic systems.