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Related Concept Videos

Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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...
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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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...
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...

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Isopropyl 4-chloro-3,5-dinitro-benzoate.

Xiao-Xi Tai1, Jing Sun

  • 1Guangdong Food and Drug Vocational College, Guangzhou 510520, People's Republic of China.

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

This study details the molecular structure of a chlorinated nitrobenzene derivative. Analysis reveals specific dihedral angles of nitro and ester groups and highlights weak intermolecular interactions in its crystal lattice.

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 chemical behavior and physical properties.
  • Nitroaromatic compounds and their derivatives are important in various chemical applications, including pharmaceuticals and materials science.

Purpose of the Study:

  • To elucidate the detailed molecular structure of the title compound, C(10)H(9)ClN(2)O(6), through crystallographic analysis.
  • To investigate the spatial orientation of functional groups (nitro and ester) relative to the benzene ring.
  • To identify and characterize intermolecular interactions within the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and confirm the molecular structure.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

  • Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
  • Intermolecular interactions, such as hydrogen bonds and short non-bonded contacts, were identified using crystallographic data.

    • Main Results:

    • The crystal structure of C(10)H(9)ClN(2)O(6) was successfully determined.
    • Specific dihedral angles were quantified: 49.42°(13)/87.61°(13) for the two nitro groups and 9.10°(10) for the ester group, relative to the benzene ring.
    • A weak C-H⋯O intermolecular interaction and a short Cl⋯O contact (2.972 Å) were observed in the crystal lattice.

    Conclusions:

    • The study provides precise structural data for the chlorinated nitrobenzene derivative, C(10)H(9)ClN(2)O(6).
    • The observed dihedral angles indicate a specific conformation of the molecule in the solid state.
    • The identified intermolecular interactions offer insights into crystal packing and potential intermolecular forces influencing the compound's properties.