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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
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...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
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...
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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Related Experiment Video

Updated: May 22, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

5-Chloro-2-nitro-phenol.

Dong-Mei Ren1

  • 1Security and Environment Engineering College, Capital University of Economics and Business, Beijing 10070, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 17, 2012
PubMed
Summary

This study details the crystal structure of C(6)H(4)ClNO(3), revealing specific molecular arrangements and hydrogen bonding interactions. These interactions form a complex three-dimensional network within the crystal lattice.

Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding molecular structure and intermolecular interactions is crucial for predicting material properties.
  • C(6)H(4)ClNO(3) is a compound with potential applications in various chemical fields.
  • Previous studies may not have fully elucidated the detailed crystal packing and hydrogen bonding network of this specific compound.

Purpose of the Study:

  • To determine the precise crystal structure of C(6)H(4)ClNO(3).
  • To investigate the intra- and intermolecular hydrogen bonding patterns.
  • To analyze the formation of a three-dimensional network through various bonding interactions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the crystal structure.

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  • The asymmetric unit was examined, revealing two independent molecules.
  • Hydrogen bonding and non-covalent interactions were identified and characterized.

    • Main Results:

    • The dihedral angles between the benzene ring and nitro groups were found to be 2.5(1)° and 8.5(1)°.
    • Intramolecular hydrogen bonds formed S(6) six-membered rings involving hydroxy and nitro groups.
    • A three-dimensional network was constructed via O-H⋯O, O-H⋯Cl, C-H⋯O hydrogen bonds, and Cl⋯O contacts.

    Conclusions:

    • The crystal structure of C(6)H(4)ClNO(3) exhibits specific molecular conformations and significant intermolecular interactions.
    • The identified hydrogen bonding network plays a key role in stabilizing the crystal structure.
    • Further research could explore the implications of this structure on the compound's physical and chemical properties.