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Related Concept Videos

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)01:19

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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 acid...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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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...
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...

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Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
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The hunt for HCO(aq).

Svend Knak Jensen1, Søren Rud Keiding, Jan Thøgersen

  • 1Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Aarhus C, Denmark. thogersen@chem.au.dk.

Physical Chemistry Chemical Physics : PCCP
|June 22, 2010
PubMed
Summary

The aqueous formyl radical (HCO(aq)) was not detected after formate photolysis. Experiments suggest it is highly unstable, reacting with water in under a picosecond.

Area of Science:

  • Photochemistry
  • Aqueous solution chemistry
  • Radical reactions

Background:

  • The formyl radical (HCO) is well-known in gas-phase reactions.
  • HCO has not been previously identified in aqueous solutions.
  • Understanding radical behavior in water is crucial for various chemical processes.

Purpose of the Study:

  • To identify the aqueous formyl radical (HCO(aq)) as a photoproduct.
  • To investigate the stability and reactivity of HCO(aq) in water.
  • To explore the photolysis of aqueous formate anions at 200 nm.

Main Methods:

  • Infrared femtosecond transient absorption spectroscopy.
  • Photolysis of aqueous formate anions (HCOO-(aq)) via excitation of the (n pi*) transition at 200 nm.

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Main Results:

  • The aqueous formyl radical (HCO(aq)) was not observed.
  • Evidence suggests HCO(aq) has an extremely short lifetime in water.
  • The transient species reacts with surrounding water molecules in less than one picosecond.

Conclusions:

  • The aqueous formyl radical (HCO(aq)) is transient and highly unstable.
  • HCO(aq) rapidly reacts with water, explaining its absence in aqueous solution studies.
  • This study provides insights into the short-lived intermediates in aqueous photochemistry.