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Related Concept Videos

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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:
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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.
As with other organic compounds, alcohols and phenols...

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4-Acetyl-3-[2-(eth-oxy-carbon-yl)phen-yl]sydnone.

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

David A Grossie1, Kenneth Turnbull, Sandra Felix-Balderrama

  • 1Department of Chemistry, Wright State University, 3640 Colonel Glenn Hwy, Dayton, Ohio 45435, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

Sydnones are mesoionic compounds requiring aromatic substitution for stability. This study details the crystal structure of a specific sydnone derivative, revealing its twisted conformation and intermolecular interactions like pi-pi stacking and hydrogen bonding.

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Published on: January 3, 2018

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Sydnones are mesoionic heterocyclic compounds.
  • Aromatic substitution at the N-3 position is generally required for sydnone stability.
  • The title compound features a 2-acetamido-phenyl substituent.

Purpose of the Study:

  • To characterize the crystal structure of the sydnone compound C(10)H(9)N(3)O(3).
  • To investigate the molecular conformation and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and intermolecular distances.

Main Results:

  • The compound C(10)H(9)N(3)O(3) was structurally characterized.
  • The sydnone and phenyl rings exhibit a significant twist with an inter-planar angle of 63.13(5)°.
  • Molecules pack via π-π interactions between phenyl rings (3.4182(4) Å) and sydnone rings (3.2095(4) Å).
  • Intra- and intermolecular N-H⋯O and C-H⋯O hydrogen bonds were observed.

Conclusions:

  • The crystal structure provides insights into the conformational preferences of substituted sydnones.
  • Intermolecular forces, including π-π stacking and hydrogen bonding, play a crucial role in the packing of these molecules.
  • This structural data contributes to understanding the solid-state properties of mesoionic compounds.