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[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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Diazonium Group Substitution: –OH and –H01:19

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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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Structure of Conjugated Dienes

Introduction
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...
Indicators02:39

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Certain organic substances change color in dilute solution when the hydronium ion concentration reaches a particular value. For example, phenolphthalein is a colorless substance in any aqueous solution with a hydronium ion concentration greater than 5.0 × 10−9 M (pH < 8.3). In more basic solutions where the hydronium ion concentration is less than 5.0 × 10−9 M (pH > 8.3), it is red or pink. Substances such as phenolphthalein, which can be used to determine the pH of a solution, are called...

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3-(Diphenyl-methyl-idene)indolin-2-one.

Maosen Yuan1, Qi Wang, Shujun Zhang

  • 1College of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China.

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

This study details the propeller-like structure of a C(21)H(15)NO molecule, revealing specific dihedral angles between its indoline-2-one and benzene groups. The crystal structure shows molecules linked into chains via hydrogen bonding.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • The molecule C(21)H(15)NO features an indoline-2-one core with two benzene substituents.
  • Understanding the spatial arrangement of these groups is crucial for predicting molecular properties.

Purpose of the Study:

  • To elucidate the three-dimensional structure and crystal packing of the title molecule.
  • To characterize the dihedral angles and intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles was performed.

Main Results:

  • The molecule adopts a propeller-like conformation around the central carbon atom.
  • Key dihedral angles were measured: 73.32° between benzene rings and 76.54°/67.69° between benzene rings and the indoline-2-one group.
  • An intermolecular N-H⋯O hydrogen bond was identified, forming chains along the c-axis.

Conclusions:

  • The study provides precise structural data for C(21)H(15)NO.
  • The observed propeller-like arrangement and hydrogen bonding dictate the molecule's packing in the solid state.