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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.4K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.4K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.1K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.1K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.6K
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...
14.6K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
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...
3.4K
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

1.9K
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...
1.9K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.3K
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...
17.3K

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Cyclohexane Vibrations: High-Resolution Spectra and Anharmonic Local Mode Calculations.

Peter F Bernath1, Edwin L Sibert Iii2

  • 1Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia 23529, United States.

The Journal of Physical Chemistry. A
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High-resolution infrared spectra reveal complex vibrational interactions in cyclohexane. Anharmonic local mode calculations explain how CH2 scissor modes perturb C-H stretching, organizing molecular energy levels.

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Area of Science:

  • Molecular Spectroscopy
  • Vibrational Dynamics
  • Quantum Chemistry

Background:

  • Cyclohexane, an oblate symmetric top molecule with D3 symmetry, exhibits complex vibrational spectra.
  • Understanding its vibrational modes is crucial for interpreting spectra of larger cyclic systems.

Purpose of the Study:

  • To record and analyze high-resolution infrared absorption spectra of cyclohexane.
  • To investigate the interactions between CH2 scissor modes and C-H stretching modes.
  • To elucidate the organization of vibrational energy levels in cyclohexane.

Main Methods:

  • High-resolution infrared absorption spectroscopy at room temperature and 241 K.
  • Rotational analysis of specific vibrational modes (ν27 and ν14).
  • Anharmonic local mode calculations for spectral interpretation.

Main Results:

  • Detailed spectra of cyclohexane recorded from 1100 to 4000 cm-1.
  • Rotational analysis of ν27 (eu) and ν14 (a2u) CH2 scissor modes.
  • Assignment of combination modes and identification of perturbations on C-H stretching modes by CH2 scissor overtones/combinations.
  • Observation of four main C-H stretching modes as two a2u eu pairs near 2862 and 2933 cm-1.

Conclusions:

  • Anharmonic local mode calculations are essential for interpreting perturbed C-H stretching modes.
  • Fermi-resonance coupling terms provide insight into the organization of cyclohexane's vibrational energy levels.
  • Cyclohexane serves as a model for understanding vibrational behavior in larger six-membered ring systems.