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Related Concept Videos

Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...
Molecular Geometry and Dipole Moments02:36

Molecular Geometry and Dipole Moments

The VSEPR theory can be used to determine the electron pair geometries and molecular structures as follows:
Phosphodiester Linkages01:01

Phosphodiester Linkages

Overview
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
DNA and RNA are polynucleotides or long chains of nucleotides that are linked together. A nucleotide is...
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...

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Related Experiment Video

Updated: Jun 11, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Hydrogen bonding in phosphine oxide/phosphate-phenol complexes.

Ruud Cuypers1, Ernst J R Sudhölter, Han Zuilhof

  • 1Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen,The Netherlands.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|July 6, 2010
PubMed
Summary

Researchers developed a new solvent-impregnated resin (SIR) for removing phenols and thiophenols. Trialkylphosphine oxide shows promise as an extractant, with strong binding affinities for phenols and thiophenols in water treatment applications.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

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Last Updated: Jun 11, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

  • Environmental Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Phenols and thiophenols are common water pollutants requiring efficient removal methods.
  • Solvent-impregnated resins (SIRs) offer a promising approach for selective pollutant extraction.
  • Understanding complex formation mechanisms is crucial for designing effective SIR systems.

Purpose of the Study:

  • To investigate the complexation of phosphine oxides and phosphates with phenols and thiophenols.
  • To evaluate the potential of these compounds as extractants in novel SIR systems for water remediation.
  • To compare the efficacy of various computational methods and experimental techniques in studying these interactions.

Main Methods:

  • Isothermal titration calorimetry (ITC) was used for experimental binding studies.
  • Quantum chemical modeling, including B3LYP, M06-2X, MP2, SCS-MP2, MP2/CBS, and CBS-Q methods, was employed for theoretical analysis.
  • The PCM solvent model was used to investigate solvent effects computationally.

Main Results:

  • Trialkylphosphine oxide demonstrated significant binding enthalpies (e.g., -14.5 kcal mol(-1) with phenol via MP2/CBS).
  • Dimethyl phosphate showed the strongest binding (-15.1 kcal mol(-1) via MP2/CBS) due to dual hydrogen bonding, but suffered from competing dimer formation.
  • SCS-MP2 and M06-2X computational methods showed good agreement with the more rigorous MP2/CBS method for predicting binding affinities.

Conclusions:

  • Trialkylphosphine oxides are identified as highly promising extractants for phenol removal in SIR systems.
  • Phosphate-based extractants, while strong binders, face challenges with dimer formation impacting practical application.
  • SCS-MP2 and M06-2X offer computationally efficient and accurate alternatives for studying such molecular interactions.