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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Some thio-ether-ketones and their related derivatives.

Molly A O'Connor1, Anna V Pavlishchuk2,3, Raymond J Butcher4

  • 1Department of Chemistry Drexel University, 3141 Chestnut St Philadelphia PA 19104-2816 USA.

Acta Crystallographica. Section E, Crystallographic Communications
|June 9, 2025
PubMed
Summary

This study details the structural characteristics of five novel thio-ether-ketones and pyridyl-hydrazone derivatives. Three compounds exhibit conformational enantiomerism, with DFT calculations revealing hydrogen bonding and weak C-H⋯S interactions.

Keywords:
crystal structureintra- and inter­molecular hydrogen bondingthio­ether ketones derivatives

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Investigation of novel sulfur- and nitrogen-containing organic compounds.
  • Exploration of structural diversity and stereochemistry in synthesized molecules.
  • Understanding intermolecular interactions in the solid state.

Purpose of the Study:

  • To characterize the structural properties of five new compounds: Dtdpe, Mtdp, Dhpk, Prpsb, and Ctrsp.
  • To investigate the phenomenon of conformational enantiomerism in the solid state.
  • To analyze intra- and intermolecular hydrogen bonding using DFT calculations.

Main Methods:

  • Single-crystal X-ray diffraction for structural determination.
  • Density Functional Theory (DFT) calculations for analyzing intermolecular interactions.
  • Spectroscopic methods for compound characterization (implied).

Main Results:

  • Detailed structural elucidation of two thio-ether-ketones (Dtdpe, Mtdp) and three pyridyl-hydrazone derivatives (Dhpk, Prpsb, Ctrsp).
  • Observation of conformational enantiomerism in three of the five synthesized compounds.
  • Identification of significant N-H⋯N and N-H⋯S hydrogen bonds, alongside weaker C-H⋯S interactions.

Conclusions:

  • The synthesized compounds exhibit diverse structural features, including conformational enantiomerism.
  • Hydrogen bonding plays a crucial role in the solid-state packing of these molecules.
  • DFT calculations provide valuable insights into the nature and strength of intermolecular forces.