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Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and...
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The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
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Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
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In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
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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.
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In ¹H NMR spectroscopy, acidic protons (–COOH) of carboxylic acids are highly deshielded and absorb far downfield, at around 9–12 ppm. The chemical shift value depends on the concentration and solvent used.
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Ethyl 1H-indole-2-carboxyl-ate.

Will E Lynch1, Christine R Whitlock1, Clifford W Padgett1

  • 1Georgia Southern University, Department of Chemistry and Biochemistry, Box 8064, Statesboro, GA 30460, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

Researchers synthesized ethyl 1H-indole-2-carboxylate, an indole derivative, for potential chelator applications. The compound crystallizes as hydrogen-bonded dimers, forming a herringbone molecular packing structure.

Keywords:
crystal structurehydrogen bondingindole

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Tris indole compounds are explored for their potential as chelating agents.
  • Understanding the synthesis and crystal structure of indole derivatives is crucial for developing new materials.

Purpose of the Study:

  • To synthesize and crystallize ethyl 1H-indole-2-carboxylate.
  • To investigate the molecular packing and hydrogen bonding interactions in the crystal structure.

Main Methods:

  • Synthesis of ethyl 1H-indole-2-carboxylate via thionyl chloride reaction of 1H-indole-2-carboxylic acid followed by dissolution in ethanol.
  • X-ray crystallography to determine the molecular and crystal structure.

Main Results:

  • Successful synthesis and crystallization of ethyl 1H-indole-2-carboxylate (C11H11NO2).
  • Observation of a herringbone molecular packing pattern with zigzag along the b-axis.
  • Formation of hydrogen-bonded dimers through O⋯H-N interactions, creating centrosymmetric R22(10) ring motifs.

Conclusions:

  • Ethyl 1H-indole-2-carboxylate was synthesized and its crystal structure elucidated.
  • The study reveals specific hydrogen bonding and molecular packing characteristics important for supramolecular assembly.