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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 Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Composition of Polyprotic Acid Solutions as a Function of pH01:19

Composition of Polyprotic Acid Solutions as a Function of pH

Polyprotic acids of the type H2M constitute two ionizable protons. As a result, on titration with a base, they exhibit two equivalence points in the titration curve. During titration, the species H2M, HM−, and M2− will be present in the solution at different points. The fractions of H2M, HM−, and M2− present at the various instances of the titration are denoted by α0, α1, and α2, respectively.
A graph with the alpha values is plotted against the volume of base added during titration. Here, a...
Polyprotic Acids03:38

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

Gallic acid pyridine monosolvate.

Fu-Yue Dong1, Jie Wu, Hai-Yan Tian

  • 1Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of gallic acid and pyridine monosolvate. Hydrogen bonding and pi-pi interactions create a unique three-dimensional network in the crystal structure.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Gallic acid (3,4,5-trihydroxybenzoic acid) is a naturally occurring phenolic acid with diverse biological activities.
  • Understanding the crystal structure of gallic acid derivatives is crucial for developing new materials and pharmaceuticals.
  • Pyridine is a basic heterocyclic organic compound widely used in chemical synthesis.

Purpose of the Study:

  • To elucidate the crystal structure of the gallic acid-pyridine monosolvate.
  • To investigate the intermolecular interactions, including hydrogen bonding and pi-pi stacking, within the crystal lattice.
  • To understand the formation of the three-dimensional network in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding networks (O-H...N, O-H...O) and their geometric parameters.
  • Investigation of pi-pi interactions between aromatic rings (pyridine-pyridine and pyridine-benzene).

Main Results:

  • The gallic acid molecule is essentially planar with an intramolecular O-H...O hydrogen bond.
  • An intermolecular O-H...N hydrogen bond links gallic acid and pyridine molecules.
  • The crystal structure features a three-dimensional network stabilized by intermolecular hydrogen bonds and pi-pi interactions between aromatic rings.

Conclusions:

  • The crystal structure of gallic acid-pyridine monosolvate is characterized by a robust three-dimensional network.
  • Hydrogen bonding and pi-pi interactions play critical roles in stabilizing the crystal lattice.
  • This structural understanding could inform the design of novel crystalline materials with tailored properties.