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Related Concept Videos

Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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2-[4-(Morpholin-4-ylmeth-yl)phen-yl]benzonitrile.

Gangadhar Y Meti1, R R Kamble, A J Ravi

  • 1Department of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka, India.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study details the molecular structure of C18H18N2O, revealing a specific chair conformation of the morpholine ring and its dihedral angles relative to benzene rings. Crystal analysis found no significant intermolecular interactions.

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Facile Preparation of 4-Substituted Quinazoline Derivatives

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Morpholine derivatives are common scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

  • To elucidate the precise molecular geometry and crystal packing of the title compound, C18H18N2O.
  • To characterize the conformational preferences of the morpholine ring and its orientation relative to aromatic systems.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
  • Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular conformation.

Main Results:

  • The morpholine ring in C18H18N2O adopts a chair conformation with the exocyclic N-C bond in an equatorial position.
  • Key dihedral angles were measured: 87.87(7)° between the central benzene and morpholine rings, and 52.54(7)° between the central benzene and cyano-benzene rings.
  • The crystal structure lacks significant intermolecular interactions, indicating isolated molecular units.

Conclusions:

  • The study provides a detailed structural description of C18H18N2O, highlighting its specific conformation.
  • The observed conformational preference and lack of intermolecular interactions offer fundamental insights for further chemical and material applications.