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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
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.
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:
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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...
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.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

3-(p-Anis-yl)sydnone.

Hoong-Kun Fun, Jia Hao Goh, Nithinchandra

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a sydnone compound, 3-(4-meth-oxy-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate. Molecular interactions like C-H⋯O hydrogen bonds and π-π stacking dictate its sheet-like crystal packing.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Sydnone compounds are a class of mesoionic heterocycles with diverse chemical properties.
    • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical behavior.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of the sydnone compound 3-(4-meth-oxy-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate.
    • To analyze the spatial arrangement and bonding within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
    • Intermolecular interactions, including hydrogen bonding and π-π stacking, were identified and quantified.

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    Published on: June 13, 2022

    Main Results:

    • The oxadiazole ring within the sydnone compound is essentially planar, with a maximum deviation of 0.005 Å.
    • The planar oxadiazole ring is inclined at a dihedral angle of 30.32° relative to the benzene ring.
    • Adjacent molecules form sheets parallel to the (100) plane through intermolecular C-H⋯O hydrogen bonds.
    • Weak intermolecular π-π interactions with a centroid-centroid distance of 3.5812 Å contribute to crystal stabilization.

    Conclusions:

    • The crystal structure reveals a specific arrangement of the sydnone compound influenced by its planar heterocyclic and aromatic rings.
    • Intermolecular C-H⋯O hydrogen bonds and π-π interactions are key factors in the observed sheet-like crystal packing.
    • This structural information is valuable for the design and synthesis of novel sydnone derivatives with tailored properties.