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Related Concept Videos

Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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Vibrational Spectra of a N719-Chromophore/Titania Interface from Empirical-Potential Molecular-Dynamics Simulation, Solvated by a Room Temperature Ionic Liquid
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Vibrational Spectra of a N719-Chromophore/Titania Interface from Empirical-Potential Molecular-Dynamics Simulation, Solvated by a Room Temperature Ionic Liquid

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Optimized intermolecular potential for nitriles based on Anisotropic United Atoms model.

Mohamed Kamel Hadj-Kali1, Vincent Gerbaud, Xavier Joulia

  • 1Université de Toulouse, Laboratoire de Génie Chimique, UMR 5503 CNRS-UPS-INPT, BP 1301, 5 Rue Paulin Talabot, 31106, Toulouse Cedex 1, France. Mohamed.HadjKali@ensiacet.fr

Journal of Molecular Modeling
|May 15, 2008
PubMed
Summary

A new intermolecular potential model for nitriles accurately predicts vapor-liquid equilibrium. This model shows excellent agreement with experimental data for acetonitrile and other nitrile compounds.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry

Background:

  • Accurate molecular models are crucial for predicting the thermodynamic properties of chemical substances.
  • Existing models for nitriles may not fully capture their complex intermolecular interactions.

Purpose of the Study:

  • To develop and validate an extended anisotropic united atoms (AUA) intermolecular potential model for nitriles.
  • To improve the prediction of vapor-liquid equilibrium (VLE) properties for nitrile compounds.

Main Methods:

  • Utilized Mulliken population analysis for atomic charges to model electrostatic interactions.
  • Employed transferable AUA4 repulsion-dispersion parameters and regressed Lennard-Jones parameters for nitrile groups.
  • Performed Gibbs Ensemble Monte Carlo (GEMC) simulations to calculate VLE data.

Main Results:

  • The developed AUA model shows very good agreement with experimental VLE data for acetonitrile.
  • The model's predictions for acetonitrile surpass the accuracy of previous molecular potentials.
  • Successfully transferred the potential to accurately predict VLE for propionitrile and n-butyronitrile without re-parameterization.

Conclusions:

  • The extended anisotropic united atoms model provides a robust and transferable description of nitrile intermolecular interactions.
  • This model significantly enhances the ability to predict VLE properties for various nitrile compounds.
  • The findings offer a valuable tool for computational studies involving nitriles.