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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.
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Base-Stabilized Phosphinidene Oxide, Imide and Sulfide.

Aliona G Baradzenka1, Sergei F Vyboishchikov2, Melanie Pilkington1

  • 1Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario, L2S 3A1, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 25, 2023
PubMed
Summary

This study details the synthesis and characterization of novel phosphinidene oxides, dioxides, and sulfides. These compounds undergo unique reactions, including P=O/N=C metathesis and cycloaddition, yielding complex organophosphorus structures.

Keywords:
Iminophosphoranephosphinidenephosphinidene imidephosphinidene oxidephosphinidene sulfide

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Area of Science:

  • Organophosphorus Chemistry
  • Inorganic Synthesis
  • Reaction Mechanisms

Background:

  • Phosphinidenes are highly reactive intermediates crucial in organophosphorus chemistry.
  • Stabilized phosphinidenes offer a pathway to explore their unique reactivity.
  • Understanding the oxidation and functionalization of phosphinidenes is key to developing new synthetic methodologies.

Purpose of the Study:

  • To synthesize and characterize novel oxidized derivatives of base-stabilized phosphinidenes.
  • To investigate the reactivity of phosphinidene oxides and imines with various reagents.
  • To elucidate reaction mechanisms using computational methods and structural analysis.

Main Methods:

  • Oxidation of a base-stabilized phosphinidene using N2O and pyridine oxide.
  • Trapping reactions with isocyanates and azides.
  • Characterization using NMR spectroscopy, single-crystal X-ray diffraction (SC XRD), and Density Functional Theory (DFT) calculations.

Main Results:

  • Isolation and characterization of phosphinidene oxide, dioxide, and sulfide derivatives.
  • Observation of P=O/N=C metathesis leading to urea-ligated phosphines.
  • Formation of transient imines and subsequent cycloaddition or P,N-heterocycle synthesis.
  • Elucidation of reaction pathways via DFT calculations.

Conclusions:

  • Base-stabilized phosphinidenes serve as versatile precursors for a range of oxidized and functionalized organophosphorus compounds.
  • The study expands the known reactivity of phosphinidenes, showcasing novel metathesis and cycloaddition pathways.
  • Comprehensive characterization provides valuable insights into the structure and bonding of these unique molecules.