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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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.
5.5K
Ion Exchange01:17

Ion Exchange

937
Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
937
Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

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Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
4.7K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.4K
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,...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

7.4K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Updated: Dec 6, 2025

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry
13:06

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry

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A novel exchange method to access sulfated molecules.

Jaber A Alshehri1, Anna Mary Benedetti1, Alan M Jones2

  • 1School of Pharmacy, University of Birmingham, Edgbaston, B15 2TT, UK.

Scientific Reports
|October 7, 2020
PubMed
Summary

A new double ion-exchange method simplifies the synthesis of organosulfates and sulfamates. This efficient technique uses readily available reagents and is suitable for sensitive molecules, yielding good to excellent results.

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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange
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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange

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Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand
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Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand

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Last Updated: Dec 6, 2025

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry
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Author Spotlight: Functionalizing Metal-Organic Frameworks: Advancements, Challenges, and the Power of Post-Synthetic Ligand Exchange
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Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand
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Sulfate Separation by Selective Crystallization with a Bis-iminoguanidinium Ligand

Published on: September 8, 2016

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Organosulfates and sulfamates are crucial bioactive molecules.
  • Their polar nature presents significant challenges in preparation and purification.

Purpose of the Study:

  • To develop an operationally simple and efficient method for synthesizing organosulfates and sulfamates.
  • To provide an alternative sulfation route addressing the demand for complementary synthetic strategies.

Main Methods:

  • A novel 3-step procedure utilizing tributylamine as a solubilizing agent.
  • A double ion-exchange method employing commercially available sulfating agents.
  • The use of TriButylSulfoAmmonium Betaine (TBSAB) as an inspiration for reagent development.

Main Results:

  • Successful synthesis of organosulfates and sulfamates with good to excellent isolated yields.
  • The method is applicable to various substituted benzyl alcohols, benzylamines, and aniline.
  • The procedure can be performed at low temperatures, accommodating sensitive substrates.

Conclusions:

  • The developed method offers an inexpensive, molecularly efficient, and solubilizing cation-exchanging route.
  • This approach provides a valuable alternative for the synthesis of organosulfates and sulfamates.
  • The technique is versatile and amenable to a range of substrates and conditions.