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Related Concept Videos

π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...
π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
[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.
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Related Experiment Video

Updated: Jun 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

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Published on: August 16, 2018

1-Allyl-3,3-diphenyl-indolin-2-one.

S Nirmala, E Theboral Sugi Kamala, L Sudha

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    This study details the molecular structure of a novel oxindole compound. Its planar oxindole core is nearly perpendicular to phenyl rings, with packing stabilized by hydrogen bonds.

    Area of Science:

    • Organic Chemistry
    • Crystallography

    Background:

    • Oxindole derivatives are important scaffolds in medicinal chemistry.
    • Understanding the solid-state structure of organic compounds is crucial for predicting their properties.

    Purpose of the Study:

    • To elucidate the crystal structure and molecular geometry of a specific oxindole compound (C23H19NO).
    • To investigate the intermolecular interactions governing the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
    • Analysis of dihedral angles and intermolecular interactions (hydrogen bonds, C-H⋯N interactions).

    Main Results:

    • The oxindole residue exhibits a planar geometry.

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    Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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    A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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    Published on: August 16, 2018

    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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    Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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    Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

    Published on: May 27, 2015

  • The phenyl rings are positioned almost perpendicularly to the oxindole core, with dihedral angles of 72.1° and 77.6°.
  • Molecular packing is significantly influenced by C-H⋯O hydrogen bonds and C-H⋯N interactions.

    • Conclusions:

    • The study provides detailed structural insights into the C23H19NO oxindole derivative.
    • The identified intermolecular interactions are key to understanding the compound's solid-state behavior and potential applications.