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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...
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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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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...
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The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
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Ethyl 2-[(2-oxo-2H-chromen-6-yl)-oxy]acetate.

Navneet Goyal1, James P Donahue2, Anthony Thompson1

  • 1Department of Chemistry, Xavier University of Louisiana, 1 Drexel Dr., New Orleans, Louisiana 70125, USA.

Acta Crystallographica. Section E, Crystallographic Communications
|June 7, 2024
PubMed
Summary

This study details the crystal structure of ethyl 2-[(2-oxo-2H-chromen-6-yl)-oxy]acetate, a coumarin derivative. The coumarin molecules form sheets reinforced by hydrogen bonds and π-π stacking interactions.

Keywords:
chromen-2-onecoumarincrystal structuresheet structureweak C—H⋯O H-bondingπ–π stacking

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Coumarins are a pharmacologically significant class of organic compounds.
  • Understanding the crystal structure of coumarin derivatives is crucial for their applications.
  • Ethyl 2-[(2-oxo-2H-chromen-6-yl)-oxy]acetate is a specific coumarin derivative with potential biological activity.

Purpose of the Study:

  • To determine and describe the crystal structure of ethyl 2-[(2-oxo-2H-chromen-6-yl)-oxy]acetate.
  • To elucidate the intermolecular interactions governing the crystal packing.
  • To provide insights into the solid-state behavior of this coumarin derivative.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • The crystal system and space group were identified (monoclinic, C2/c).
  • Intermolecular interactions, including hydrogen bonding and π-π stacking, were analyzed.

Main Results:

  • The compound crystallizes in monoclinic space group C2/c, forming sheet-like structures.
  • Molecules within the sheets are related by inversion centers and 21 axes.
  • Weak C-H⋯O hydrogen bonds and coumarin π-π stacking interactions stabilize the crystal lattice.

Conclusions:

  • The crystal structure reveals a layered arrangement stabilized by specific weak interactions.
  • The findings contribute to the understanding of coumarin crystal engineering.
  • This structural information can inform the design of new coumarin-based materials and pharmaceuticals.