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Related Concept Videos

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.

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2,3,4,5,6-Penta-fluoro-trans-cinnamic acid.

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Acta Crystallographica. Section E, Structure Reports Online
|October 8, 2013
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structure of a fluorinated carboxylic acid, C9H3F5O2. It forms dimers and sheet-like structures stabilized by various intermolecular interactions, including hydrogen bonds and fluorine contacts.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Fluorine Chemistry

Background:

  • Understanding the crystal packing of organic molecules is crucial for predicting material properties.
  • Fluorinated organic compounds exhibit unique intermolecular interactions due to fluorine's high electronegativity.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C9H3F5O2.
  • To identify and analyze the intermolecular interactions governing its crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of intermolecular contacts, including hydrogen bonds, C-H···F, O···F, F···F, and π-π interactions.

Main Results:

  • The compound crystallizes as carboxylic acid dimers linked by O-H···O hydrogen bonds.
  • Sheet-like structures are formed through a combination of C-H···F, O···F, and F···F interactions.
  • These sheets are further stacked by π-π interactions, with an observed intramolecular C-H···F interaction.

Conclusions:

  • The crystal structure of C9H3F5O2 is characterized by a complex network of intermolecular interactions.
  • Hydrogen bonding and fluorine-mediated contacts play a significant role in stabilizing the observed sheet-like architecture.
  • The study provides insights into the supramolecular assembly of fluorinated carboxylic acids.