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Related Concept Videos

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.4K
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...
1.4K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

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

1.8K
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.
1.8K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

16.7K
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...
16.7K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

17.3K
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...
17.3K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

11.9K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
11.9K
Prochirality02:05

Prochirality

5.4K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
5.4K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Cyclopropanone: Preparation, Rotational Spectroscopy, and Semi-Experimental Equilibrium (reSE) Structure.

W Hazel Styers1, Brian J Esselman1, Samuel A Wood1

  • 1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society
|March 30, 2026
PubMed
Summary

We analyzed the rotational spectra of cyclopropanone isotopologues, providing data for radioastronomical searches. This study also determined a precise molecular structure, highlighting challenges in theoretical chemistry predictions.

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Astrochemistry

Background:

  • Cyclopropanone is a key organic molecule with limited gas-phase data.
  • Previous studies lacked comprehensive spectroscopic analysis for radioastronomical applications.

Purpose of the Study:

  • To measure and analyze the microwave and millimeter-wave rotational spectra of cyclopropanone and its isotopologues.
  • To establish foundational spectral data for radioastronomical searches of cyclopropanone.
  • To determine the precise equilibrium structure of cyclopropanone through experimental data.

Main Methods:

  • Gas-phase rotational spectroscopy (microwave and millimeter-wave) was employed.
  • Synthesis of stable cyclopropanone oligomers allowed monomer generation under vacuum.
  • Analysis of 10 isotopologues provided 30 moments of inertia for structure determination.

Main Results:

  • Comprehensive spectral data were obtained for cyclopropanone and nine isotopologues.
  • Hyperfine-resolved rotational transitions were identified, crucial for low-temperature interstellar observations.
  • The first complete semiexperimental equilibrium structure (rSEe) of cyclopropanone was determined with high precision.

Conclusions:

  • The experimental spectral data enable radioastronomical searches for cyclopropanone in cold interstellar clouds.
  • The determined rSEe structure serves as an experimental benchmark for organic molecules.
  • Discrepancies between experimental and high-level theoretical structures highlight challenges in computational chemistry for precise molecular geometry prediction.