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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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Based on their attached substituent groups, ethers can be classified into two...
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Structure and Nomenclature of Epoxides

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 is more in the ring having a smaller number of...
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
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Crown Ethers02:36

Crown Ethers

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.
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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(E)-1,2-Bis(4-fluoro-phen-yl)ethane-1,2-dione.

Hoong-Kun Fun1, Reza Kia

  • 1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

This study details a unique substituted benzil structure featuring an elongated central carbon-carbon bond. This structural anomaly is attributed to minimizing dipole-dipole interactions and facilitating pi-system overlap in the crystalline solid.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Benzil derivatives are important organic compounds with diverse applications.
  • Understanding the conformational preferences and bonding characteristics of benzil derivatives is crucial for predicting their reactivity and properties.

Purpose of the Study:

  • To characterize the molecular structure and conformation of a novel substituted benzil compound.
  • To investigate the unusual C-C bond length and its implications for electronic interactions.
  • To analyze the intermolecular interactions governing the crystal packing.

Main Methods:

  • Single crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, torsion angles, and intermolecular contacts was performed.
  • Computational methods may be used to further investigate electronic effects (though not explicitly stated in the abstract).

Main Results:

  • The compound exhibits an s-trans conformation of the dicarbonyl unit with a significant O-C-C-O torsion angle.
  • An unusually long central C-C bond (1.536 Å) was observed between the carbonyl groups.
  • Weak intermolecular C-H···O hydrogen bonds and π-π stacking interactions stabilize the crystal structure.

Conclusions:

  • The elongated C-C bond is likely a consequence of reducing unfavorable vicinal dipole-dipole interactions between the oxygen atoms.
  • Orbital overlap between the dione and the benzene rings' π systems contributes to the observed structure.
  • The crystal packing is influenced by a combination of hydrogen bonding and π-π interactions, highlighting the interplay of forces in solid-state structures.