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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
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...
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...
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...
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,...
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...

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

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Cyclopentadecanone.

Eric A Noe1, Diwakar M Pawar, Frank R Fronczek

  • 1Department of Chemistry, Jackson State University, 1400 J. R. Lynch Street, Jackson, MS 39217-0510, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|February 7, 2008
PubMed
Summary
This summary is machine-generated.

Exaltone (C15H28O) crystal structure reveals a non-disordered, quinquangular conformation. Temperature adjustment to 90 K resolves nonmerohedral twinning, correcting previous literature findings.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • The crystal structure of exaltone (C15H28O), a 15-membered macrocyclic ketone, has been previously described with disorder.
  • Understanding the precise molecular conformation and crystalline arrangement is crucial for its applications.

Purpose of the Study:

  • To accurately determine and describe the crystal structure of exaltone.
  • To clarify the nature of twinning and its dependence on temperature.
  • To correct inaccuracies in the existing literature regarding exaltone's crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Variable-temperature crystallographic studies.
  • Structural refinement and analysis.

Main Results:

  • Exaltone crystallizes without disorder in a quinquangular [13353] C(1) symmetry conformation.
  • The crystal exhibits nonmerohedral twinning, which can be treated as pseudo-merohedral at 90 K.
  • The previously reported disordered orthorhombic structure with a halved a-axis length is corrected.

Conclusions:

  • The precise crystal structure of exaltone has been elucidated, revealing a specific conformation and symmetry.
  • Temperature-dependent twinning behavior was characterized, providing a more accurate structural model.
  • This study corrects and refines the understanding of exaltone's solid-state properties.