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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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...
Ionic Bonding and Electron Transfer02:48

Ionic Bonding and Electron Transfer

Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions.
Electrophiles02:28

Electrophiles

This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Ions as Acids and Bases02:54

Ions as Acids and Bases

Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
Mass Spectrometry: Alkyl Halide Fragmentation01:22

Mass Spectrometry: Alkyl Halide Fragmentation

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 1:1...
Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

Dialkyl chloronium ions.

Evgenii S Stoyanov1, Irina V Stoyanova, Fook S Tham

  • 1Department of Chemistry, University of California, Riverside, California 92521-0403, USA. evgeniis@ucr.edu

Journal of the American Chemical Society
|March 12, 2010
PubMed
Summary
This summary is machine-generated.

Carborane acid reacts with chloroalkanes to form stable dialkylchloronium salts. These salts offer a clean synthetic route to potent electrophilic methylating agents, useful in chemical synthesis.

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Area of Science:

  • Inorganic Chemistry
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Carborane acids are strong acids with unique properties.
  • Dialkylchloronium ions are reactive intermediates.

Purpose of the Study:

  • To synthesize and characterize novel dialkylchloronium ion salts.
  • To explore their stability and reactivity.
  • To develop a new methylating agent.

Main Methods:

  • Reaction of carborane acid H(CHB(11)Cl(11)) with chloroalkanes.
  • X-ray crystallography for structural determination.
  • Infrared (IR) spectroscopy for vibrational analysis.

Main Results:

  • Isolable dialkylchloronium ion salts [R(2)Cl][CHB(11)Cl(11)] were synthesized and found to be stable at room temperature.
  • X-ray structures revealed bent cation geometries (C-Cl-C angles of 101.5-105.8°).
  • Heating the dimethylchloronium salt yielded a sublimable methylating agent CH(3)(CHB(11)Cl(11)).

Conclusions:

  • Dialkylchloronium salts derived from carborane acid are stable and structurally characterized.
  • A new, potent electrophilic methylating agent was developed.
  • This work expands the utility of carborane chemistry in synthesis.