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Crown Ethers02:36

Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
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Structure and Nomenclature of Epoxides02:38

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Halogens03:01

Halogens

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Fluoren-9-one oxime.

Bernhard Bugenhagen1, Yosef Al Jasem2, Mariam Al-Azani3

  • 1Institute for Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|April 26, 2014
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a fluorene-based molecule (C13H9NO), revealing intramolecular hydrogen bonding and intermolecular O-H⋯N hydrogen bonds that form chains. These chains exhibit pi-pi stacking interactions between fluorene systems.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular packing and intermolecular interactions is crucial for materials science.
  • Fluorene derivatives are known for their unique photophysical properties and potential applications.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of a specific fluorene-based molecule (C13H9NO).
  • To investigate the role of hydrogen bonding and pi-pi stacking in the solid-state organization of the molecule.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Analysis of non-covalent interactions, including hydrogen bonds and pi-pi stacking, was performed.

Main Results:

  • The fluorene system and oxime group are nearly coplanar in the molecule.
  • Intramolecular C-H⋯O hydrogen bonding forms an S(6) ring.
  • Intermolecular O-H⋯N hydrogen bonds link molecules into [100] chains.
  • Chains exhibit pi-pi stacking interactions between fluorene rings with a 3.347 Å inter-planar distance.
  • A short C-H⋯π contact is observed between adjacent chains.

Conclusions:

  • The crystal structure is dictated by a combination of intramolecular and intermolecular interactions.
  • The observed packing arrangement, including hydrogen bonding and pi-pi stacking, influences the molecule's solid-state properties.
  • This structural insight provides a foundation for designing fluorene-based materials with tailored properties.