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Related Concept Videos

Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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...
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Published on: February 6, 2019

Homothiacalix[4]arenes: synthetic exploration and solid-state structures.

Joice Thomas1, Kristof Van Hecke, Koen Robeyns

  • 1Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven (KUL), Celestijnenlaan 200F, 3001 Leuven, Belgium.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 5, 2011
PubMed
Summary
This summary is machine-generated.

This study optimizes synthetic routes for homothiacalix[4]arenes, enabling easier access to these macrocycles for supramolecular chemistry applications. New functionalization and oxidation methods were also developed and characterized.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Macrocyclic Chemistry

Background:

  • Homothiacalixarenes are structurally unique macrocycles with potential in host-guest chemistry.
  • Their synthesis and functionalization remain less explored compared to related calixarenes.

Purpose of the Study:

  • To reinvestigate and optimize synthetic protocols for homothiacalix[4]arenes.
  • To explore inner-rim functionalization and bridge oxidation of these macrocycles.
  • To characterize the conformational properties of novel homothiacalixarene derivatives.

Main Methods:

  • Optimization of macrocyclization reactions for homothiacalixarene synthesis.
  • Development of ester functionalization on the inner rim of the macrocycles.
  • Oxidation of the dimethylenethia bridge within the macrocyclic structure.
  • Characterization using variable-temperature Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography.

Main Results:

  • Straightforward access to the parent homothiacalix[4]arene skeleton achieved through optimized protocols.
  • Successful synthesis of bis and tetrakis ester-functionalized homothiacalix[4]arenes.
  • Successful oxidation of the dimethylenethia bridge demonstrated.
  • Conformational analyses provided by NMR and X-ray studies elucidated macrocycle structures.

Conclusions:

  • Optimized synthetic routes provide facile access to homothiacalix[4]arenes.
  • Novel functionalization and oxidation strategies expand the utility of homothiacalixarenes.
  • Detailed structural and conformational insights were gained for these macrocycles.