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Related Concept Videos

Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Polyprotic Acids03:38

Polyprotic Acids

Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

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...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
Acid–Base Equilibria: Activity-Based Definition of pH01:10

Acid–Base Equilibria: Activity-Based Definition of pH

For an ideal solution, the pH is defined as the negative logarithm of the hydrogen ion concentration. For a non-ideal solution, an accurate measurement of the pH must consider the negative logarithm of the hydrogen ion activity rather than concentration. In such a solution, the pH can be more accurately defined as the negative logarithm of a product of the hydrogen ion concentration and its activity coefficient.
In solutions of very low ionic strength—for example, pure water—the activity...
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...

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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Host-guest interactions in acid-porphyrin complexes.

Matthew J Webb1, Stéphanie Deroo, Carol V Robinson

  • 1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.

Chemical Communications (Cambridge, England)
|August 16, 2012
PubMed
Summary

Researchers utilized weak interactions of acid-porphyrin complexes to selectively bind acids to a cyclic porphyrin dimer. The study characterized these interactions using NMR spectroscopy and nano-electrospray ionisation spectrometry.

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Last Updated: May 19, 2026

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry

Background:

  • Porphyrin dimers are macrocyclic compounds with potential applications in molecular recognition.
  • Selective binding of guest molecules is crucial for developing advanced chemical sensors and separation materials.

Purpose of the Study:

  • To investigate the selective binding of competing acids to a rigid cyclic porphyrin dimer.
  • To characterize the interactions between the acid-porphyrin complexes using advanced spectroscopic techniques.

Main Methods:

  • Utilizing weak interactions between acid-porphyrin complexes for selective binding.
  • Employing Nuclear Magnetic Resonance (NMR) spectroscopy for interaction characterization.
  • Using nano-electrospray ionisation spectrometry for detailed analysis of the complexes.

Main Results:

  • Demonstrated selective binding of specific acids to the porphyrin dimer faces.
  • Provided detailed characterization of the resulting acid-porphyrin complexes.
  • Confirmed the efficacy of weak interactions in driving selective molecular assembly.

Conclusions:

  • Weak interactions offer a viable strategy for selective acid binding within porphyrin macrocycles.
  • NMR spectroscopy and nano-electrospray ionisation spectrometry are powerful tools for studying supramolecular interactions.