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Related Concept Videos

Nomenclature of Aromatic Compounds with a Single Substituent01:23

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).
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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...
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Benzene-1,2-dicarb-oxy-lic acid-pyridinium-2-olate (1/1).

Chua-Hua Yu1

  • 1Orderd Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|July 19, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a compound formed by o-phthalic acid and pyridin-2-ol. The molecules form zigzag chains through hydrogen bonding, revealing insights into molecular interactions.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the self-assembly of organic molecules is crucial in materials science.
  • Phthalic acid derivatives and pyridine-based compounds are widely studied for their diverse chemical properties.
  • Investigating zwitterionic forms provides insights into charge distribution and intermolecular interactions.

Purpose of the Study:

  • To characterize the crystal structure of the compound formed between o-phthalic acid and pyridin-2-ol.
  • To elucidate the intermolecular interactions, including hydrogen bonding, within the crystal lattice.
  • To analyze the conformational aspects of the o-phthalate and pyridin-2-ol moieties.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided conformational details.
  • Hydrogen bonding networks were identified and characterized using geometric parameters.

Main Results:

  • The asymmetric unit contains one molecule of o-phthalic acid and one zwitterionic pyridin-2-ol molecule.
  • The carboxylate groups of o-phthalic acid exhibit significant twisting from the benzene ring (dihedral angles of 13.6° and 73.1°).
  • The hydroxyl hydrogen atom of the pyridin-2-ol moiety is disordered over two positions (1:1 ratio).
  • O-H⋯O and N-H⋯O hydrogen bonds link the molecules into zigzag chains along the [-101] direction.

Conclusions:

  • The crystal structure reveals a specific arrangement driven by hydrogen bonding interactions.
  • The zwitterionic nature of pyridin-2-ol and the conformation of o-phthalic acid influence the overall packing.
  • This study contributes to the understanding of crystal engineering with organic acids and heterocyclic compounds.