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Related Concept Videos

Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Gallic Acid.

Jianping Zhao, Ikhlas A Khan, Frank R Fronczek

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study reveals that anhydrous 3,4,5-trihydroxy-benzoic acid is nearly planar. Its crystal structure features cyclic dimers and a 3D network formed by hydrogen bonds involving carboxyl and phenolic groups.

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    Ganglioside Extraction, Purification and Profiling

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • 3,4,5-trihydroxy-benzoic acid, also known as gallic acid, is a phenolic acid with diverse biological activities.
    • Understanding its anhydrous crystal structure is crucial for its applications in pharmaceuticals and materials science.

    Purpose of the Study:

    • To determine the precise molecular and crystal structure of anhydrous 3,4,5-trihydroxy-benzoic acid.
    • To investigate the hydrogen bonding patterns within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to elucidate the structure.
    • Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
    • Graph set analysis was used to characterize the hydrogen bonding motifs.

    Main Results:

    • The anhydrous acid is essentially planar, with minimal deviations of non-hydrogen atoms from coplanarity.
    • Carboxyl groups form centrosymmetric hydrogen-bonded cyclic dimers (R(2)(2)(8)).
    • Phenolic hydroxyl groups engage in both intra- and intermolecular hydrogen bonds, creating a 3D network.

    Conclusions:

    • The planar nature and extensive hydrogen bonding network dictate the solid-state properties of anhydrous 3,4,5-trihydroxy-benzoic acid.
    • The detailed structural information provides a foundation for predicting and controlling its behavior in various applications.