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Related Concept Videos

π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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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...
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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...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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Related Experiment Video

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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
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Dimethyl biphenyl-4,4'-dicarboxyl-ate.

Verena Ritzerfeld1, Axel Pyrlik, Yutian Wang

  • 1Institut für Anorganische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany.

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

This study details the crystal structure of a biphenyl-dicarboxylic acid ester. The molecule forms a typical molecular crystal without hydrogen bonds, with minimal deviation from planarity.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Biphenyl-dicarboxylic acid esters are important organic compounds.
  • Understanding molecular packing is crucial for material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(16)H(14)O(4).
  • To analyze the molecular geometry and intermolecular interactions in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Least-squares plane analysis was performed to assess molecular planarity.

Main Results:

  • The asymmetric unit contains half a molecule, with the full molecule generated by an inversion center.
  • The biphenyl-dicarboxylic acid ester moiety is essentially planar, with minor deviations at methyl groups (max 0.124(2) Å).
  • The crystal structure is characterized as a typical molecular crystal lacking classical hydrogen bonds.

Conclusions:

  • The compound crystallizes as a discrete molecular entity.
  • Intermolecular contacts are consistent with van der Waals forces, indicating weak interactions.