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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.6K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.6K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.6K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.6K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.3K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.3K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.3K
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.4K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Methanesulfonyl Iodide.

Pradeepa Rajakaruna1, John D Gorden1, David M Stanbury1

  • 1Dept. of Chemistry and Biochemistry , Auburn University , Auburn , Alabama 36849 , United States.

Inorganic Chemistry
|October 23, 2019
PubMed
Summary
This summary is machine-generated.

Methanesulfonyl iodide (CH3SO2I) is synthesized in aqueous solutions via the reaction of triiodide and methanesulfinate. Its rapid formation and subsequent slow decomposition to sulfonate were characterized, providing insights into its chemical behavior.

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

  • Inorganic Chemistry
  • Physical Chemistry
  • Crystallography

Background:

  • Methanesulfonyl iodide (CH3SO2I) is an important intermediate in chemical synthesis.
  • Understanding its formation, stability, and reactivity in aqueous solutions is crucial for its effective utilization.
  • Previous studies have not fully elucidated the kinetics and equilibrium of its formation and decomposition pathways.

Purpose of the Study:

  • To investigate the production of methanesulfonyl iodide (CH3SO2I) in aqueous solutions.
  • To characterize the crystalline structures of its complexes with potassium and rubidium iodides.
  • To determine the equilibrium constant for its formation and the rate of its hydrolysis.

Main Methods:

  • Synthesis of methanesulfonyl iodide (CH3SO2I) from triiodide and methanesulfinate.
  • X-ray crystallography to determine the structure of (CH3SO2I)4·KI3·2I2 and (CH3SO2I)2·RbI3.
  • Spectrophotometry and stopped-flow kinetics to study the rapid equilibrium of CH3SO2I formation.
  • Hydrolysis experiments to determine the decomposition rate constant (khyd).

Main Results:

  • Dichroic crystals of (CH3SO2I)4·KI3·2I2 and (CH3SO2I)2·RbI3 were successfully synthesized and characterized.
  • X-ray crystallography revealed that CH3SO2I molecules coordinate via oxygen atoms to metal cations with an S-I bond length of 2.44 Å.
  • The equilibrium constant for CH3SO2- + I3- ⇌ CH3SO2I + 2I- was determined to be K_MSI = 1.07 ± 0.01 M.
  • The equilibrium was established within ~2 ms, and CH3SO2I solutions showed an absorbance maximum at 309 nm.
  • The hydrolysis rate constant was found to be khyd = 2.0 × 10^-4 s^-1, exhibiting an inverse-squared dependence on [I-].

Conclusions:

  • Methanesulfonyl iodide (CH3SO2I) is readily formed in aqueous solutions and can be isolated as crystalline complexes.
  • The rapid equilibrium of CH3SO2I formation and its subsequent slow decomposition are key aspects of its solution chemistry.
  • The inverse-squared dependence of the hydrolysis rate on iodide concentration is explained by the preceding equilibrium.