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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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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.
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Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Published on: January 19, 2016

Methyl 2,6-dicarboxybenzoate.

Sophie H Dale1, Mark R J Elsegood

  • 1Chemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 25, 2003
PubMed
Summary
This summary is machine-generated.

Regioselective methylation of hemimellitic acid produced a novel 2-methyl ester. This compound features a unique crystal structure with methyl ester groups interacting with hydrogen-bonded zigzag chains.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Hemimellitic acid is a tricarboxylic acid with potential applications in materials science.
  • Understanding the regioselective functionalization of such molecules is crucial for developing new chemical entities.

Purpose of the Study:

  • To synthesize and characterize the 2-methyl ester of hemimellitic acid.
  • To investigate the crystal packing and intermolecular interactions of the synthesized compound.

Main Methods:

  • Regioselective methylation of hemimellitic acid in basic methanol.
  • Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.

Main Results:

  • Successful synthesis of the title 2-methyl ester (C10H8O6).
  • The crystal structure reveals a unique packing arrangement where methyl ester groups are situated between zigzag chains formed by hydrogen bonding.
  • The hydrogen bonding utilizes a head-to-tail carboxylic acid-acid dimer motif.

Conclusions:

  • The study demonstrates a successful regioselective methylation of hemimellitic acid.
  • The determined crystal structure provides insights into the supramolecular assembly driven by hydrogen bonding and steric interactions.