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Related Concept Videos

Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
For example, cyclohexane molecular ions have a mass-to-charge ratio (m/z) of 84, which tends to produce a stronger signal than linear alkanes like hexane. This stability comes from...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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...
Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.

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Related Experiment Video

Updated: Jun 17, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Phosphate monoester hydrolysis in cyclohexane.

Randy B Stockbridge1, Richard Wolfenden

  • 1Department of Biochemistry and Biophysics, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27514, USA.

Journal of the American Chemical Society
|December 24, 2009
PubMed
Summary

Enzyme-catalyzed phosphate monoester hydrolysis is challenging. Transferring substrates from water to cyclohexane dramatically enhances hydrolysis rates, primarily due to increased entropy of activation.

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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
15:22

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

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Last Updated: Jun 17, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
15:22

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

Published on: April 3, 2014

Area of Science:

  • Biochemistry
  • Chemical Kinetics
  • Enzyme Catalysis

Background:

  • Phosphate monoester hydrolysis is a difficult reaction, often catalyzed by enzymes.
  • Enzyme catalysis may involve substrate extraction from aqueous solution.
  • Phosphohydrolases are enzymes that catalyze the hydrolysis of phosphate esters.

Purpose of the Study:

  • To investigate the effect of transferring phosphate monoester substrates from water to an organic solvent on hydrolysis rates.
  • To determine if substrate extraction influences catalytic effects observed in phosphohydrolase activity.

Main Methods:

  • Synthesized the tetrabutylammonium salt of neopentyl phosphate.
  • Dissolved the salt in wet cyclohexane to achieve measurable hydrolysis rates.
  • Measured the second-order rate constant for hydrolysis in the organic solvent.

Main Results:

  • The tetrabututylammonium salt of neopentyl phosphate dissolved in wet cyclohexane at measurable concentrations.
  • Hydrolysis rate constant for the phosphomonoester dianion was enhanced approximately 2 x 10(12)-fold upon transfer from water to cyclohexane.
  • This rate enhancement was attributed to an increase in the entropy of activation.

Conclusions:

  • Extraction of phosphate monoester substrates from water into a non-polar solvent significantly enhances hydrolysis rates.
  • The observed rate enhancement is primarily driven by favorable entropic changes upon transfer.
  • This finding supports the hypothesis that substrate partitioning plays a crucial role in the catalytic efficiency of phosphohydrolases.