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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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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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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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

3.0K
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.
3.0K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

15.8K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Radicals: Electronic Structure and Geometry01:07

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
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4.3K
Cycloalkanes02:28

Cycloalkanes

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Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Doubly Fused Unsymmetrical Calixdicarbahexaphyrins.

Shubham Tiwari1, Rima Sengupta1, K N Panda1

  • 1Department of Chemistry, IIT Bombay, Powai, Mumbai 400076, India.

The Journal of Organic Chemistry
|April 29, 2022
PubMed
Summary

Novel unsymmetrical calixdicarbahexaphyrins were synthesized, featuring unusual fused ring structures. These macrocycles exhibit unique electronic properties and a saddle-shaped conformation, confirmed by spectroscopic and computational analyses.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Calixphyrins are macrocyclic compounds with diverse applications.
  • Unsymmetrical macrocycles present unique structural and electronic properties.
  • Synthesis of complex fused macrocyclic systems remains a challenge.

Purpose of the Study:

  • To synthesize novel doubly fused unsymmetrical calixdicarbahexaphyrins.
  • To elucidate the structural features and electronic properties of these new macrocycles.
  • To investigate the impact of unusual fusion patterns on macrocyclic properties.

Main Methods:

  • Mild acid-catalyzed (4+2) condensation of dicarbatetrapyrrane with dipyrroethene diol.
  • Oxidation of condensation products.
  • Single-crystal X-ray diffraction analysis.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 1H-1H COSY, NOESY, 13C, HMBC).
  • UV-Vis absorption spectroscopy.
  • Electrochemical studies.
  • Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) calculations.

Main Results:

  • Successful synthesis of three novel doubly fused unsymmetrical calixdicarbahexaphyrins.
  • Unusual fusion patterns observed, leading to tripentacyclic and fused pentacycle/hexacycle ring systems.
  • Crystal structure revealed a saddle-shaped conformation with an sp3 carbon disrupting π-electron delocalization.
  • Spectroscopic and electrochemical studies indicated electron-rich, non-aromatic character.
  • DFT/TD-DFT calculations supported experimental findings.

Conclusions:

  • The study presents a novel synthetic route to complex unsymmetrical calixdicarbahexaphyrins.
  • Unusual fusion modes significantly influence the macrocyclic framework and electronic properties.
  • The synthesized compounds offer potential for new materials with tailored electronic characteristics.