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Ionic Crystal Structures02:42

Ionic Crystal Structures

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Ionic crystals consist of two or more different kinds of ions that usually have different sizes. The packing of these ions into a crystal structure is more complex than the packing of metal atoms that are the same size.
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...
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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...
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sp3d and sp3d 2 Hybridization
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Electrophilic Addition to Alkynes: Halogenation02:38

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Calix[4]arene-fused phospholes.

Fethi Elaieb1, David Sémeril, Dominique Matt

  • 1Laboratoire de Chimie Inorganique Moléculaire et Catalyse, Institut de Chimie (UMR 7177 CNRS), Université de Strasbourg, 1 rue Blaise Pascal, F-67008 Strasbourg Cedex, France. dmatt@unistra.fr dsemeril@unistra.fr.

Dalton Transactions (Cambridge, England : 2003)
|July 7, 2017
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Summary

Researchers synthesized a novel calixarene-fused phosphole, a unique ligand for palladium and rhodium catalysis. This new compound efficiently catalyzes styrene hydroformylation, yielding high regioselectivity for branched aldehydes.

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Area of Science:

  • Organometallic Chemistry
  • Supramolecular Chemistry
  • Catalysis

Background:

  • Calix[4]arenes are versatile macrocyclic hosts with tunable properties.
  • Biarylphosphines are crucial ligands in homogeneous catalysis, particularly for palladium and rhodium complexes.
  • Developing novel phosphine ligands with controlled steric and electronic properties is key to advancing catalytic efficiency and selectivity.

Purpose of the Study:

  • To synthesize and characterize a novel upper rim, o-(diphenylphosphinyl)phenyl-substituted calix[4]arene.
  • To investigate the coordination chemistry and catalytic applications of the derived calixarene-fused phospholes.
  • To explore the influence of the calixarene scaffold on the properties and catalytic activity of phosphole ligands.

Main Methods:

  • Synthesis of a novel calix[4]arene derivative featuring an o-(diphenylphosphinyl)phenyl substituent.
  • Palladium-catalyzed conversion of the biarylphosphine precursor into two diastereomeric calixarene-fused phospholes.
  • Complexation studies with rhodium, including characterization of the resulting organometallic complexes.
  • Evaluation of the catalytic performance in styrene hydroformylation.

Main Results:

  • Successful preparation of a unique calixarene-fused phosphole ligand with a fixed P lone pair orientation.
  • Formation of rhodium complexes where the metal center is positioned near the calixarene unit, inducing unusual NMR chemical shifts.
  • The rhodium-acetonitrile complex, in conjunction with the phosphole ligand, efficiently catalyzes styrene hydroformylation with high regioselectivity for branched aldehydes (b/l ratio up to 30).

Conclusions:

  • The synthesized calixarene-fused phosphole serves as an effective ligand in organometallic chemistry and catalysis.
  • The unique structure of the ligand influences the coordination environment of the metal center and catalytic outcomes.
  • This study demonstrates a novel route to functionalized phospholes integrated within a supramolecular scaffold for catalytic applications.