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Related Concept Videos

Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)01:19

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...
2D NMR: Overview of Heteronuclear Correlation Techniques01:18

2D NMR: Overview of Heteronuclear Correlation Techniques

Heteronuclear correlation spectroscopy is an analytical technique that investigates the coupling between different types of nuclei, often a proton and an X-nucleus, such as carbon-13 or nitrogen-15. This method is commonly used in nuclear magnetic resonance (NMR) spectroscopy to gain insights into complex chemical compounds' structural and compositional aspects. A typical heteronuclear correlation spectrum displays X-nucleus chemical shifts on one axis and a proton spectrum on the other axis.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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...
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β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

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Crown ether complexes of HPCl6.

Zin-Min Tun1, Matthew J Panzner, Vincenzo Scionti

  • 1Department of Chemistry, University of Akron, Akron, Ohio 44325-3601, USA.

Journal of the American Chemical Society
|November 18, 2010
PubMed
Summary

New superacid complexes, HPCl6, were synthesized using HCl, PCl5, and crown ethers. Crystal structures reveal proton positioning within the crown ether molecules, impacting complex formation and stability.

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Area of Science:

  • Inorganic Chemistry
  • Supramolecular Chemistry
  • Crystal Engineering

Background:

  • Superacids are highly acidic compounds capable of protonating even weak bases.
  • Crown ethers are cyclic polyethers known for their ability to complex metal cations.
  • The interaction of protons with crown ethers is less explored but crucial for understanding superacid behavior.

Purpose of the Study:

  • To synthesize and characterize novel superacid complexes involving protonated crown ethers.
  • To investigate the structural details of these complexes using X-ray crystallography.
  • To understand the role of crown ether structure in stabilizing the superacid HPCl6.

Main Methods:

  • Reaction of hydrogen chloride (HCl), phosphorus pentachloride (PCl5), and crown ethers (12-crown-4 or 18-crown-6) in chloroform (CHCl3).
  • Isolation and purification of the resulting complexes: [H(12-crown-4)][PCl6] and [H(18-crown-6)2][PCl6].
  • Single-crystal X-ray diffraction analysis to determine the precise molecular and crystal structures.

Main Results:

  • Successful synthesis of two new superacid complexes containing protonated crown ethers.
  • Crystal structure of [H(12-crown-4)][PCl6] shows the proton centrally located within the 12-crown-4 molecule.
  • Crystal structure of [H(18-crown-6)2][PCl6] reveals the proton situated between oxygen atoms of two distinct 18-crown-6 molecules.

Conclusions:

  • Crown ethers can effectively stabilize the superacid HPCl6 through proton complexation.
  • The size and structure of the crown ether dictate the mode of proton binding.
  • These findings offer insights into the design of novel proton-conducting materials and supramolecular assemblies.