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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.
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Preparation and Reactions of Thiols02:33

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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.
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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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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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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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Drug Metabolism: Phase II Reactions01:14

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

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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.
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Direct Organosulfate Production from Terpenoid-SO2 Interactions in the Aqueous Phase.

Xiangyu Zhang1,2,3, Junting Qiu1,2,3, Xinming Wang1,2,3

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Environmental Science & Technology
|January 6, 2026
PubMed
Summary

Dissolved sulfur dioxide (SO2) directly forms organosulfates (OSs) with biogenic terpenoids in atmospheric water, explaining previously unknown aerosol mass. This SO2 pathway is significant for atmospheric chemistry and climate models.

Keywords:
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Area of Science:

  • Atmospheric Chemistry
  • Aerosol Science
  • Organic Geochemistry

Background:

  • Organosulfates (OSs) are crucial components of secondary organic aerosols (SOAs).
  • A significant portion of ambient SOA mass remains chemically unexplained.
  • Biogenic terpenoids are abundant volatile organic compounds in the atmosphere.

Purpose of the Study:

  • To investigate the direct reaction of dissolved sulfur dioxide (SO2) with biogenic terpenoids.
  • To quantify the formation rates of organosulfates (OSs) via this novel pathway.
  • To assess the contribution of this reaction to atmospheric organosulfate loading and aerosol properties.

Main Methods:

  • Electrospray ionization mass spectrometry (ESI-MS) for product identification.
  • Kinetic experiments in varying solvent mixtures (acetonitrile/water) to determine rate constants.
  • pH-dependent studies to simulate cloud and aerosol water conditions.

Main Results:

  • Direct reaction of SO2 with terpenoids (α-pinene, β-pinene, d-limonene, β-caryophyllene, α-terpineol) forms OSs without traditional oxidants.
  • Second-order rate constant for α-pinene + SO2 determined as 4.0 ± 0.9 M⁻¹s⁻¹ in 50% acetonitrile/water, increasing with water content.
  • Reaction rates at pH 3-5 (cloud/aerosol conditions) are significant (60-80 M⁻¹s⁻¹ for α-pinene), comparable to known oxidant pathways.

Conclusions:

  • The direct reaction of dissolved SO2 with terpenoids is a viable pathway for OS formation in atmospheric condensed phases.
  • This mechanism can explain a substantial fraction of unexplained SOA mass.
  • Incorporating this chemistry into models will improve predictions of aerosol composition, acidity, and climate impact.