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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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...
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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).
NMR Spectroscopy of Benzene Derivatives01:37

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...

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2-[2-(2,4-Dinitro-phen-yl)eth-yl]-1,3,5-trinitro-benzene.

Zhi-Hua Wei1, Wen-Yan Wang, Ying Diao

  • 1School of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary

This study details the molecular structure of C(14)H(9)N(5)O(10), revealing specific dihedral angles between benzene rings and nitro groups. Weak intermolecular hydrogen bonding was also observed in its crystal structure.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
  • Nitro-substituted aromatic compounds are important in various chemical applications, necessitating detailed structural characterization.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(14)H(9)N(5)O(10).
  • To quantify the dihedral angles between the aromatic rings and the orientation of the nitro groups relative to these rings.
  • To identify and describe any significant intermolecular interactions, such as hydrogen bonding, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
  • Analysis of the resulting crystal structure data to calculate dihedral angles and identify hydrogen bonding networks.

Main Results:

  • The crystal structure of C(14)H(9)N(5)O(10) was successfully determined.
  • A dihedral angle of 14.81° was measured between the two benzene rings.
  • Nitro groups exhibited varying degrees of twist relative to the benzene rings, with angles ranging from 2.80° to 62.58°.
  • Weak intermolecular C-H⋯O hydrogen bonds were identified as a feature of the crystal packing.

Conclusions:

  • The study provides precise geometric parameters for C(14)H(9)N(5)O(10), highlighting significant deviations from planarity due to nitro group substitution.
  • The observed hydrogen bonding network contributes to the stabilization of the crystal structure.
  • These structural insights are valuable for computational modeling and understanding structure-property relationships in related compounds.