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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.6K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

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Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...
11.7K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.2K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.2K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.8K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.8K

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Updated: Jun 14, 2025

Fast and Specific Assessment of the Halogenating Peroxidase Activity in Leukocyte-enriched Blood Samples
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Leveraging Chlorination-Based Mechanism for Resolving Subcellular Hypochlorous Acid.

Fung Kit Tang1, Lawrence Tucker1, Maheshwara Reddy Nadiveedhi1

  • 1Department of Chemistry & Biochemistry, Clarkson University, NY, 13676, United States.

Biorxiv : the Preprint Server for Biology
|September 4, 2024
PubMed
Summary

New HOCl indicators, HOClSense dyes, offer a novel chlorination-based mechanism for precise sub-cellular detection. This breakthrough enables better understanding of cellular processes and disease mechanisms related to hypochlorous acid (HOCl) levels.

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Area of Science:

  • Biomedical Engineering
  • Chemical Biology
  • Cellular Biology

Background:

  • Hypochlorous acid (HOCl) is vital for immunity but its dysregulation causes inflammation and tissue damage.
  • Current HOCl detection methods rely on oxidation, potentially misrepresenting chlorinative stress.
  • Accurate visualization of HOCl in sub-cellular compartments is needed to understand its biological roles.

Purpose of the Study:

  • To develop novel indicators for sensitive and selective detection of HOCl in sub-cellular environments.
  • To introduce a new chlorination-based sensing mechanism distinct from oxidation methods.
  • To enable visualization of HOCl dynamics within specific organelles and cellular compartments.

Main Methods:

  • Design and synthesis of a new series of HOCl indicators, termed HOClSense dyes.
  • Utilizing a chlorination-based sensing mechanism for HOCl detection.
  • Employing click chemistry for functionalization and targeting specific sub-cellular locations like plasma membrane and lysosomes.

Main Results:

  • HOClSense dyes demonstrate switch-on/off detection modes with diverse emission colors and redshift.
  • The indicators exhibit high selectivity for HOCl.
  • Successful subcellular HOCl mapping in plasma membrane and lysosomes.
  • Discovery of STING pathway-induced HOCl production and abnormal HOCl in Niemann-Pick diseases.

Conclusions:

  • HOClSense represents the first chlorination-based indicator series for resolving sub-cellular HOCl.
  • This new tool provides unprecedented insights into HOCl biology and pathology.
  • The findings pave the way for understanding HOCl's role in immune response and diseases.