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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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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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UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

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UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a...
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Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

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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.
As with other organic compounds, alcohols and...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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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:
18.3K
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although...
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3-{5-Bromo-2-[(tri-phenyl-phosphanyl-idene)amino]-phen-yl}-4,5-di-hydro-1,2,3-oxa-diazol-3-ylium-5-olate.

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3-(2-Acetamido-phen-yl)sydnone.

Acta crystallographica. Section E, Structure reports online·2011
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Structure-optical property relationships in organometallic sydnones.

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Updated: May 3, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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4-Acetyl-3-[2-(eth-oxy-carbon-yl)phen-yl]sydnone.

David Grossie1, Leanna Harrison1, Kenneth Turnbull1

  • 1Department of Chemistry, Wright State University, Dayton, OH 45435, USA.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
PubMed
Summary
This summary is machine-generated.

Sydnones are mesoionic heterocyclic compounds. The study synthesized a novel sydnone derivative with an aromatic substituent, revealing insights into its structural stability and intermolecular interactions.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Sydnones are mesoionic five-membered heterocyclic compounds.
  • Aromatic substituents at the N3 position enhance sydnone stability.
  • Understanding the structural and bonding characteristics of sydnone derivatives is crucial.

Purpose of the Study:

  • To synthesize and characterize a novel sydnone derivative with a 2-(ethoxy-carbonyl)phenyl substituent.
  • To investigate the intra- and intermolecular interactions within the synthesized compound.
  • To analyze the crystal structure and molecular geometry of the title compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of hydrogen bonding networks (intra- and intermolecular).
  • Calculation of the inter-planar angle between the sydnone and phenyl rings.

Main Results:

  • The crystal structure of 4-acetyl-3-[2-(ethoxy-carbonyl)phenyl]-1,2,3-oxadiazol-3-ium-5-olate (C13H12N2O5) was determined.
  • Intra- and intermolecular hydrogen bonds were identified.
  • A significant inter-planar angle of 71.94° between the sydnone and benzene rings was observed.
  • π-ring⋯carbonyl interactions of 3.2038 Å were found between the sydnone ring and a symmetry-related carbonyl group.

Conclusions:

  • The synthesized sydnone derivative exhibits a specific molecular conformation influenced by the bulky aromatic substituent.
  • The presence of both hydrogen bonds and π-ring interactions contributes to the crystal packing and stability.
  • This study provides valuable structural data for sydnone chemistry and supramolecular assembly.