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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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

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Related Experiment Video

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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4,5-Dihydro-cyclo-penta-[b]thio-phen-6-one.

Lyall R Hanton1, Stephen C Moratti, Zheng Shi

  • 1Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.

Acta Crystallographica. Section E, Structure Reports Online
|February 21, 2012
PubMed
Summary

This study details the crystal structure of a C(7)H(6)OS compound, revealing two similar molecules. These molecules exhibit near-planarity and are arranged in columns via pi-pi and C-H...pi interactions, forming an extended network through hydrogen bonds.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
  • The title compound, C(7)H(6)OS, presents an interesting molecular framework for structural investigation.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(7)H(6)OS.
  • To analyze the molecular arrangement and intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of the crystal packing involved identifying pi-pi stacking and hydrogen bonding interactions.

Main Results:

  • The asymmetric unit contains two similar molecules of C(7)H(6)OS.
  • Both molecules are nearly planar, with slight inclinations between the thiophene and dihydro-cyclopentadienone rings.
  • Molecules are stacked into columns along the b-axis through pi-pi and C-H...pi interactions.
  • Extensive C-H...O hydrogen bonds link these columns, forming an extended network structure.

Conclusions:

  • The crystal structure of C(7)H(6)OS is characterized by planar molecules arranged in columns.
  • Intermolecular interactions, including pi-pi stacking and hydrogen bonding, dictate the formation of a 3D network.
  • This detailed structural information provides a foundation for further studies on the compound's properties and potential applications.