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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.
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IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic...
7.4K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
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.
3.2K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

10.8K
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...
10.8K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

7.6K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
7.6K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

10.4K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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2,3-Difluoro-benzoic acid.

Aleksandra A Knapik1, Wladek Minor, Maksymilian Chruszcz

  • 1University of Virginia, Department of Molecular Physiology and Biological Physics, 1340 Jefferson Park Avenue, Charlottesville, VA 22908, USA.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

2,3-Difluoro-benzoic acid molecules form stable dimers through hydrogen bonds. These dimers then stack together, further stabilized by weak interactions between carbon, hydrogen, fluorine, and oxygen atoms.

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Area of Science:

  • Crystallography and Molecular Interactions
  • Organic Chemistry

Background:

  • 2,3-Difluoro-benzoic acid is an organic compound with the chemical formula C(7)H(4)F(2)O(2).
  • Understanding the intermolecular interactions of such molecules is crucial for predicting their solid-state structures and properties.

Purpose of the Study:

  • To investigate the self-assembly and crystal packing of 2,3-Difluoro-benzoic acid.
  • To identify the key non-covalent interactions stabilizing the observed structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of intermolecular contacts, including hydrogen bonds and weaker interactions, was performed.

Main Results:

  • 2,3-Difluoro-benzoic acid molecules form centrosymmetric dimers.
  • These dimers are stabilized by a strong intermolecular hydrogen bond between the carboxylic acid groups.
  • The dimers stack into columns, which are further associated through weaker C-H⋯F and C-H⋯O interactions.

Conclusions:

  • Hydrogen bonding is the primary interaction driving the formation of dimers in 2,3-Difluoro-benzoic acid.
  • Weaker C-H⋯F and C-H⋯O interactions play a significant role in the three-dimensional crystal packing, stabilizing the stacked dimer arrangement.