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Related Concept Videos

Phosphodiester Linkages01:01

Phosphodiester Linkages

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Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Complexation Equilibria: Factors Influencing Stability of Complexes01:09

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In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Related Experiment Video

Updated: Jan 5, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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A Highly Stabilized Phosphonium Ylide that Forms Supramolecular Dimers in Solution and the Solid State.

Min Ji Kim1, Stella M Luo1, Andrew J Greenlee1

  • 1Chemistry Department, Macalester College, Saint Paul, MN, 55105, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 15, 2019
PubMed
Summary

Researchers unexpectedly synthesized a highly stabilized phosphonium ylide. This unusual compound forms stable homodimers through intermolecular interactions and shows limited reactivity, indicating significant stabilization.

Keywords:
diimidesdimerizationsupramolecular chemistryylideszwitterions

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Supramolecular Chemistry
  • Organophosphorus Chemistry

Background:

  • Bisphosphonium pyromellitic diimides are complex molecules with potential applications.
  • Phosphonium ylides are versatile intermediates in organic synthesis.

Purpose of the Study:

  • To investigate the synthesis of novel bisphosphonium pyromellitic diimides.
  • To characterize the unexpected formation and properties of a unique phosphonium ylide.

Main Methods:

  • Spectroscopic characterization (e.g., NMR, IR).
  • X-ray crystallography.
  • Solution and solid-state studies of ylide behavior.

Main Results:

  • Unexpected formation of a novel phosphonium ylide.
  • Supramolecular homodimerization of the ylide via π-π and CH⋅⋅⋅O interactions.
  • Ylide exhibits high stability, inertness to typical reactions (Wittig, alkylation), and requires strong acids for protonation.

Conclusions:

  • The synthesized phosphonium ylide is exceptionally stable due to intermolecular interactions.
  • This compound represents a significant advancement in the understanding of phosphonium ylide stabilization.
  • The findings open new avenues for exploring highly stabilized ylides in chemistry.