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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...

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

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Published on: March 24, 2018

Configuration and internal dynamics of CH2ClF...krypton.

Paolo Ottaviani1, Biagio Velino, Walther Caminati

  • 1Dipartimento di Chimica G. Ciamician dell'Università, Via Selmi 2, I-40126 Bologna, Italy.

The Journal of Physical Chemistry. A
|October 24, 2007
PubMed
Summary

The chlorofluoromethane-krypton molecular complex was studied using microwave spectroscopy. Researchers found the krypton atom tunnels between two positions, with a low energy barrier, revealing complex molecular dynamics.

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Area of Science:

  • Physical Chemistry
  • Molecular Spectroscopy
  • Quantum Mechanics

Background:

  • Understanding intermolecular forces and molecular dynamics is crucial in physical chemistry.
  • Fourier transform microwave spectroscopy provides high-resolution data on molecular structures and interactions.
  • Rare gas complexes offer insights into weak non-covalent interactions.

Purpose of the Study:

  • To investigate the structure and dynamics of the chlorofluoromethane-krypton (CH2ClF-Kr) molecular complex.
  • To determine the equilibrium configuration and intermolecular interactions within the complex.
  • To characterize the tunneling motion of the krypton atom and its associated energy barrier.

Main Methods:

  • Fourier transform microwave spectroscopy was employed to study the molecular complex in a supersonic expansion.
  • Rotational spectra of different isotopic species (CH235ClF...84Kr, CH235ClF...86Kr, CH237ClF...84Kr) were assigned.
  • Analysis of spectral splittings due to chlorine quadrupole coupling and tunneling motion was performed.

Main Results:

  • The equilibrium structure shows the krypton atom located out of the ClCF plane, interacting with both chlorine and fluorine atoms.
  • Rotational transitions exhibit splittings indicative of chlorine quadrupole interactions and a two-site tunneling motion of the krypton atom.
  • A low-energy pathway for krypton tunneling was identified, approximated by circular motion around the C-Cl bond, with an estimated barrier of ~74 cm⁻¹.

Conclusions:

  • The study elucidates the non-planar equilibrium structure and the dynamic behavior of the CH2ClF-Kr complex.
  • The observed tunneling motion highlights the subtle interplay of forces governing the complex's conformation.
  • The determined low tunneling barrier provides valuable data for theoretical modeling of weakly bound systems.