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Related Concept Videos

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...
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
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...
Mass Spectrometry: Cycloalkane Fragmentation01:05

Mass Spectrometry: Cycloalkane Fragmentation

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...
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...

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Related Experiment Video

Updated: Jun 4, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Cyclopentanone and cyclobutanone.

Dmitry S Yufit1, Judith A K Howard

  • 1Department of Chemistry, University of Durham, Durham, England. d.s.yufit@durham.ac.uk

Acta Crystallographica. Section C, Crystal Structure Communications
|March 4, 2011
PubMed
Summary
This summary is machine-generated.

Cyclopentanone and cyclobutanone crystals, both isostructural, reveal unique molecular arrangements. Antiparallel dimers and C-H...O interactions form distinct structural motifs in these organic compounds.

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Cyclopentanone and cyclobutanone are cyclic ketones with distinct ring sizes.
  • Understanding their solid-state structures is crucial for predicting chemical behavior.
  • Isostructural relationships can offer insights into molecular packing and intermolecular forces.

Purpose of the Study:

  • To investigate and characterize the crystal structures of cyclopentanone and cyclobutanone.
  • To determine the intermolecular interactions governing their solid-state arrangements.
  • To compare the structural features of these two isostructural compounds.

Main Methods:

  • In situ crystal growth of cyclopentanone and cyclobutanone on a diffractometer.
  • Single-crystal X-ray diffraction analysis to determine molecular and crystal structures.
  • Analysis of intermolecular interactions, including dipole-dipole and hydrogen bonding.

Main Results:

  • Both cyclopentanone (C(5)H(8)O) and cyclobutanone (C(4)H(6)O) were found to be isostructural.
  • Two crystallographically independent molecules exist for each compound.
  • Molecules form antiparallel dipole-dipole dimers across twofold axes.
  • Ribbons are formed by other molecules via pairs of C-H...O interactions.

Conclusions:

  • The study elucidates the detailed crystal structures of cyclopentanone and cyclobutanone.
  • Isostructurality allows for direct comparison of molecular packing and interactions.
  • Antiparallel dipole-dipole interactions and C-H...O bonds are key to their solid-state organization.