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Related Concept Videos

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.
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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
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.4K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
12.4K
Solubility03:00

Solubility

20.6K
Solution, Solubility, and Solubility Equilibrium
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
In a solution, the solute particles (molecules,...
20.6K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.5K
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,...
5.5K
Solubility Equilibria: Overview01:09

Solubility Equilibria: Overview

1.3K
When a substance such as sodium chloride is added to water, it dissolves, forming an aqueous solution. The extent of dissolution is called solubility. The process of dissolution can exist in equilibrium, just like other chemical processes. Solubility equilibria are also called precipitation equilibria because the process of solubility can be reversible. The reverse of the solubility process is called precipitation.
Solubility is important in biological and environmental processes. A notable...
1.3K

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Linear Oligosulfoxides: Synthesis and Solubility Studies.

Bhaskar Halami1, Dhananjani N A M Eriyagama1, Komal Chillar1

  • 1Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA.

Tetrahedron Letters
|December 3, 2019
PubMed
Summary
This summary is machine-generated.

Researchers synthesized linear oligosulfoxides using SN2 reactions and sodium periodate oxidation. These compounds exhibited unexpected limited solubility, challenging the "like dissolves like" principle and suggesting conformational effects influence dissolution.

Keywords:
dissolution modeloligosulfoxidepolyethylene glycolsynthesis

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Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Materials Science

Background:

  • Sulfoxide groups are highly polar, typically conferring good solubility in polar solvents.
  • Linear oligomers' solubility can be influenced by factors beyond simple polarity, such as molecular conformation.
  • Understanding solubility patterns is crucial for the application of novel chemical structures.

Purpose of the Study:

  • To synthesize linear oligosulfoxides with multiple sulfoxide functionalities.
  • To investigate the solubility behavior of these novel oligosulfoxides.
  • To explore the relationship between molecular structure, conformation, and solubility.

Main Methods:

  • Oligosulfides were synthesized via sequential SN2 reactions between alkanethiols and alkyl tosylates.
  • Oligosulfides were oxidized to oligosulfoxides using sodium periodate, carefully controlling conditions to prevent partial or over-oxidation.
  • Solubility of the synthesized oligosulfoxides was tested in various solvents, including DMSO and water.

Main Results:

  • Linear oligosulfoxides containing up to six sulfoxide groups were successfully synthesized.
  • The synthesized oligosulfoxides demonstrated limited solubility in polar solvents like DMSO and water, contrary to expectations based on the 'like dissolves like' rule.
  • The solubility was discussed in comparison to polyethylene glycol (PEG) and other polyethers, highlighting potential conformational influences.

Conclusions:

  • The unexpected solubility of oligosulfoxides suggests that molecular conformation plays a significant role in the dissolution process of linear oligomers.
  • The findings challenge the direct application of the 'like dissolves like' rule for these specific structures and propose a dissolution model based on conformational compatibility with the solvent.
  • The limited solubility observed in this study may not be indicative of all similar oligosulfoxide molecules, suggesting further investigation into structure-solubility relationships is warranted.