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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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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[6]Cyclo-2,7-naphthyl-ene: a redetermination.

Waka Nakanishi1, Jing Yang Xue, Tomoaki Yoshioka

  • 1Department of Chemistry, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|August 13, 2011
PubMed
Summary

Researchers refined the crystal structure of the macrocyclic hydrocarbon [6]cyclo-2,7-naphthylene ([6]CNAP). This study corrects previous assignments and reveals minimal strain in its naphthyl rings.

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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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Published on: March 20, 2017

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Macrocyclic hydrocarbons represent a significant class of organic compounds.
  • Previous structural determination of [6]cyclo-2,7-naphthylene ([6]CNAP) had limitations.

Purpose of the Study:

  • To prepare high-quality single crystals of [6]CNAP.
  • To accurately determine the crystal structure and molecular geometry of [6]CNAP.
  • To investigate the packing motif and intermolecular interactions in [6]CNAP crystals.

Main Methods:

  • Recrystallization of [6]CNAP from anthracene melt.
  • Single-crystal X-ray diffraction analysis.
  • Refinement of crystallographic parameters, including space group and anisotropic displacement parameters.

Main Results:

  • Obtained single crystals of [6]CNAP suitable for detailed structural analysis.
  • Corrected the space-group assignment to Cmca and refined atomic parameters.
  • Identified the smallest strain in naphthyl rings among congeners, with C2h point symmetry.
  • Observed a herringbone packing motif with short C-C (3.119 Å) and C-H (2.80 Å) distances.

Conclusions:

  • The corrected crystal structure provides precise molecular and packing information for [6]CNAP.
  • The minimal strain suggests favorable stability and potential for further functionalization.
  • The observed packing and short intermolecular contacts are crucial for understanding solid-state properties.