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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
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...
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

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High-Resolution Neutron Spectroscopy to Study Picosecond-Nanosecond Dynamics of Proteins and Hydration Water
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High-Resolution Neutron Spectroscopy to Study Picosecond-Nanosecond Dynamics of Proteins and Hydration Water

Published on: April 28, 2022

Stepwise hydration of protonated proline.

Catherine Michaux1, Johan Wouters, Eric A Perpète

  • 1Laboratoire de Chimie Biologique Structurale, Département de Chimie, Facultés Universitaires Notre-Dame de la Paix, Namur, Belgium.

The Journal of Physical Chemistry. B
|June 7, 2008
PubMed
Summary

This study details the hydration of the proline cation using advanced computational methods. Researchers identified distinct structures and energy profiles, offering insights to resolve experimental ambiguities in proline hydration.

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Sedimentation Equilibrium of a Small Oligomer-forming Membrane Protein: Effect of Histidine Protonation on Pentameric Stability
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Residue-Specific Exchange of Proline by Proline Analogs in Fluorescent Proteins: How "Molecular Surgery" of the Backbone Affects Folding and Stability
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Sedimentation Equilibrium of a Small Oligomer-forming Membrane Protein: Effect of Histidine Protonation on Pentameric Stability

Published on: April 2, 2015

Area of Science:

  • Computational Chemistry
  • Physical Chemistry
  • Biophysical Chemistry

Background:

  • Proline, an amino acid, plays a crucial role in protein structure and stability.
  • Understanding the hydration of amino acid cations is vital for elucidating their behavior in aqueous environments.
  • Protonated glycine hydration has been studied, providing a basis for comparison.

Purpose of the Study:

  • To computationally investigate the stepwise hydration of the proline cation.
  • To characterize the structures and energetics of proline cation-water clusters (0-3 water molecules).
  • To compare the hydration behavior of the proline cation with that of protonated glycine.

Main Methods:

  • Ab initio computational strategy was employed.
  • Basis set superposition error and electron-correlation effects were accounted for.
  • Structures and energies of hydrated proline cation clusters were calculated.

Main Results:

  • Structures for proline cation with 0-3 water molecules were obtained.
  • Significant differences in hydration patterns compared to protonated glycine were observed.
  • Multiple low-energy structures coexist at each hydration step, potentially explaining experimental uncertainties.
  • Theoretical enthalpies and entropies generally agree with experimental data.

Conclusions:

  • The study provides a detailed theoretical account of proline cation hydration.
  • Computational findings offer guidance for interpreting experimental results and resolving ambiguities.
  • While overall agreement with experiments is good, computed entropic changes for the third water molecule require further refinement.