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Related Concept Videos

Halogens03:01

Halogens

23.4K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Peptide Bonds02:43

Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Metal-Ligand Bonds02:51

Metal-Ligand Bonds

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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
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Bond Energies and Bond Lengths02:49

Bond Energies and Bond Lengths

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Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, that is, the energy necessary to separate the bonded atoms. Separating any pair of bonded atoms requires energy — the stronger a bond, the greater the energy required to break it.
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Bonding in Metals02:32

Bonding in Metals

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Metallic bonds are formed between two metal atoms. A simplified model to describe metallic bonding has been developed by Paul Drüde called the “Electron Sea Model”. 
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Ionic Bonds00:42

Ionic Bonds

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Overview
When atoms gain or lose electrons to achieve a more stable electron configuration they form ions. Ionic bonds are electrostatic attractions between ions with opposite charges. Ionic compounds are rigid and brittle when solid and may dissociate into their constituent ions in water. Covalent compounds, by contrast, remain intact unless a chemical reaction breaks them.
Opposing Charges Hold Ions Together in Ionic Compounds
Ionic bonds are reversible electrostatic interactions between ions...
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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A Halogen-Bond Donor Catalyst for Templated Macrocyclization.

Kévin Guillier1, Elsa Caytan1, Vincent Dorcet1

  • 1Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, 35000, Rennes, France.

Angewandte Chemie (International Ed. in English)
|August 9, 2019
PubMed
Summary
This summary is machine-generated.

This study demonstrates a novel macrocyclization method using halogen bonds to template the formation of pyridine-containing macrocycles. This approach offers a new strategy for synthesizing complex molecular architectures in solution.

Keywords:
halogen bondshydrogen transfermetathesisorganocatalysistemplate synthesis

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Computational Chemistry

Background:

  • Halogen bonding is a non-covalent interaction with potential applications in molecular recognition and self-assembly.
  • Macrocyclization is a key process in synthesizing complex organic molecules, including pharmaceuticals and materials.
  • Template-directed synthesis can improve efficiency and selectivity in macrocyclization reactions.

Purpose of the Study:

  • To report a halogen-bond templated 1:1 macrocyclization in solution.
  • To investigate the use of tetra(iodoperfluorophenyl) ethers as halogen-bonded exotemplates.
  • To synthesize pyridine-containing macrocyclic architectures via a ruthenium-catalyzed tandem reaction.

Main Methods:

  • Halogen-bond templated macrocyclization in solution.
  • Ruthenium-catalyzed tandem metathesis/transfer hydrogenation.
  • Use of sodium borohydride and methanol as a hydrogen source.
  • Density functional theory (DFT) calculations for analyzing halogen-bonded stabilization energies.

Main Results:

  • Successful 1:1 macrocyclization templated by halogen bonds.
  • Formation of pyridine-containing macrocyclic architectures.
  • Demonstration of substoichiometric use (5 mol%) of halogen-bonded exotemplates.
  • Quantification of halogen-bonded stabilization energies using DFT.

Conclusions:

  • Halogen-bond templated macrocyclization is an effective strategy for solution-phase synthesis.
  • Tetra(iodoperfluorophenyl) ethers serve as efficient exotemplates for macrocycle formation.
  • Ruthenium-catalyzed tandem reactions provide a viable route to complex pyridine-containing macrocycles.
  • DFT analysis confirms the significant role of halogen bonding in stabilizing the macrocyclic structures.