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Related Concept Videos

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of Carboxylic Acids: Overview01:31

Preparation of Carboxylic Acids: Overview

There are various methods for the preparation of carboxylic acids. For example, oxidation of primary alcohols or aldehydes using strong oxidizing agents results in a carboxylic acid. Aldehydes can also be oxidized in the presence of mild oxidizing agents.
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

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Related Experiment Video

Updated: Jun 1, 2026

Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins
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Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins

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Oxonium 2-carb-oxy-3-(2-fur-yl)acrylate.

Wen-Xian Liang1, Gang Wang, Zhi-Rong Qu

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structure of H(3)O(+)·C(8)H(5)O(5) (-), highlighting a 1D chain framework formed by hydrogen bonds. The structure is further stabilized by π-π interactions, crucial for understanding molecular assembly.

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Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins
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Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Understanding the self-assembly of molecular compounds is key in materials science.
  • Hydrogen bonds and π-π interactions are fundamental forces driving crystal structure formation.
  • The specific compound H(3)O(+)·C(8)H(5)O(5) (-) presents an interesting case for structural analysis.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, H(3)O(+)·C(8)H(5)O(5) (-).
  • To identify and characterize the intermolecular interactions responsible for the observed crystal packing.
  • To provide insights into the factors governing the stability of this molecular framework.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • Analysis of hydrogen bonding networks (O-H⋯O) was performed.
  • Investigation of π-π stacking interactions, including centroid-centroid distances, was conducted.

Main Results:

  • The crystal structure exhibits a one-dimensional chain framework along the [001] direction.
  • Neighboring cations (H(3)O(+)) and anions (C(8)H(5)O(5) (-)) are linked by robust O-H⋯O hydrogen bonds.
  • π-π interactions with a centroid-centroid distance of 3.734(3) Å further stabilize the crystal lattice.

Conclusions:

  • The crystal structure of H(3)O(+)·C(8)H(5)O(5) (-) is characterized by a 1D chain assembly driven by hydrogen bonding.
  • π-π interactions play a significant role in the overall structural stability.
  • This detailed structural understanding contributes to the broader knowledge of supramolecular chemistry and crystal engineering.