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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.
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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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.

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

4,4'-Bipyridine-3-nitro-benzoic acid (1/2).

Zhen Zhu, Feng-Qin Wang, Yong-Nan Zhao

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the unintentional synthesis of a novel compound through a hydrothermal reaction. The research reveals the transformation of 3-nitro-phthalic acid into 3-nitro-benzoic acid and the formation of a 3D supramolecular network via hydrogen bonding.

    Area of Science:

    • Coordination Chemistry
    • Supramolecular Chemistry
    • Crystallography

    Background:

    • Hydrothermal reactions offer a versatile route for synthesizing novel coordination compounds.
    • 4,4'-bipyridine is a common organic linker used in constructing metal-organic frameworks and supramolecular assemblies.
    • Phthalic acid derivatives can undergo decarboxylation reactions under specific conditions.

    Purpose of the Study:

    • To characterize the compound formed unintentionally during the hydrothermal reaction of cobalt(II) acetate, 4,4'-bipyridine, and 3-nitro-phthalic acid.
    • To investigate the in situ transformation of 3-nitro-phthalic acid under hydrothermal conditions.
    • To elucidate the crystal structure and supramolecular architecture of the resulting compound.

    Main Methods:

    • Hydrothermal synthesis.

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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    Published on: April 27, 2017

  • Single-crystal X-ray diffraction analysis.
  • Hydrogen bonding analysis (O-H...N and C-H...O).

    • Main Results:

    • The unintentional formation of a compound with the formula C(10)H(8)N(2)·2C(7)H(5)NO(4).
    • In situ decarboxylation of 3-nitro-phthalic acid to 3-nitro-benzoic acid during the reaction.
    • Formation of a 3D supramolecular network through alternating chains of 3-nitro-benzoic acid and 4,4'-bipyridine linked by O-H...N hydrogen bonds, further assembled by C-H...O hydrogen bonds.

    Conclusions:

    • The hydrothermal reaction conditions led to an unexpected decarboxylation pathway for 3-nitro-phthalic acid.
    • The resulting crystal structure exhibits a robust 3D supramolecular network driven by specific hydrogen bonding interactions.
    • This study highlights the complexity of hydrothermal synthesis and the potential for unexpected product formation and structural diversity.