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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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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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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

4.1K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.1K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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

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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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4,4'-(Acridine-2,7-di-yl)bis-(2-methyl-but-3-yn-2-ol).

Masaki Yamamura1, Seira Ikuma2, Tatsuya Nabeshima2

  • 1Center for Liberal Arts and Science Faculty of Engineering Toyama Prefectural University, 5180 Kurokawa Imizu Toyama 939-0398 Japan.

Iucrdata
|November 12, 2025
PubMed
Summary

A novel acridine derivative was synthesized using Sonogashira coupling. The resulting crystal structure features a columnar arrangement due to π-π stacking and intermolecular hydrogen bonds.

Keywords:
acridinecrystal structurehydrogen bondπ–π stacking

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Crystallography

Background:

  • Acridine derivatives are known for their diverse applications in materials science.
  • Understanding the self-assembly behavior of organic molecules is crucial for designing new functional materials.

Purpose of the Study:

  • To synthesize a novel acridine derivative with specific functional groups.
  • To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Sonogashira coupling reaction for synthesis.
  • Single-crystal X-ray diffraction for structural analysis.

Main Results:

  • Successful synthesis of the target acridine derivative (C23H21NO2).
  • Formation of a columnar structure in the crystal lattice driven by π-π stacking of acridine units.
  • Observation of intermolecular hydrogen bonds involving the 2-methyl-but-3-yn-2-ol moieties.

Conclusions:

  • The synthesized acridine derivative exhibits ordered self-assembly in the solid state.
  • The interplay of π-π stacking and hydrogen bonding dictates the crystal packing.
  • This study provides insights into the structure-property relationships of functionalized acridines.