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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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...
Intermolecular Forces03:13

Intermolecular Forces

Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen bonds, and dispersion...
Intermolecular Forces03:13

Intermolecular Forces

Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen bonds, and dispersion...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Interactions between halide anions and a molecular hydrophobic interface.

Blake M Rankin1, Michael D Hands, David S Wilcox

  • 1Department of Chemistry, Purdue University, West Lafayette, Indiana, USA.

Faraday Discussions
|June 26, 2013
PubMed
Summary

Aqueous iodide ions disrupt the hydration shell of t-butyl alcohol (TBA), unlike fluoride ions. This interaction, confirmed by spectroscopy and simulations, shows iodide prefers TBA

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Understanding ion-solvent interactions is crucial in chemistry.
  • Tert-butyl alcohol (TBA) possesses a unique tetrahedral hydration shell.
  • Halide ions are common solutes with varying interaction potentials.

Purpose of the Study:

  • To investigate the specific interactions between halide ions (fluoride and iodide) and TBA in aqueous solution.
  • To elucidate the structural impact of these ions on TBA's hydration shell.
  • To compare experimental findings with theoretical predictions.

Main Methods:

  • Utilized a novel hydration-shell spectroscopic technique.
  • Employed high signal-to-noise Raman spectroscopy combined with multivariate curve resolution (Raman-MCR).
  • Performed theoretical cluster and liquid calculations, including effective fragment potential (EFP) molecular dynamics and hybrid quantum/EFP frequency calculations.

Main Results:

  • Fluoride ions exhibit minimal interaction with TBA's hydration shell.
  • Iodide ions significantly disrupt the tetrahedral structure of TBA's hydration shell.
  • A red-shift in TBA's CH stretch frequency was observed upon iodide interaction, consistent with theoretical models.
  • Calculations indicated a higher probability of iodide, compared to fluoride, in TBA's first hydration shell.

Conclusions:

  • Iodide ions have a pronounced effect on TBA's hydration structure, while fluoride ions do not.
  • The findings highlight the differential interaction strengths of halide ions with alcohol hydration shells.
  • Experimental and theoretical methods provide complementary insights into ion-solvent interactions.