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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.8K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.0K
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,...
4.0K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.9K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
10.9K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
11.9K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.8K
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.
2.8K

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Bicyclo[1.1.1]pentane Embedded in Porphyrinoids.

Nitika Grover1, Maxime Cheveau1, Brendan Twamley2

  • 1School of Chemistry, Chair of Organic Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, The University of Dublin, 152-160 Pearse Street, D02R590, Dublin, Ireland.

Angewandte Chemie (International Ed. in English)
|March 29, 2023
PubMed
Summary

Researchers developed a new two-step method using Grignard reagents to create versatile bicyclo[1.1.1]pentane (BCP) derivatives. This enables novel BCP-containing macrocycles and calix[4]pyrrole analogues with unique structural properties.

Keywords:
Bicyclo[1.1.1]PentaneCalix[4]PyrroleGrignard ReagentsMacrocyclesPorphyrinoids

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Synthetic Methodology

Background:

  • Bicyclo[1.1.1]pentane (BCP) derivatives offer unique structural and chemical properties.
  • Incorporating strained ring systems into macrocycles can lead to novel architectures and functions.
  • Tetrapyrrolic macrocycles, like calix[4]pyrroles, are important scaffolds in various chemical applications.

Purpose of the Study:

  • To develop a versatile synthetic route to bicyclo[1.1.1]pentane (BCP) derivatives.
  • To incorporate BCP units into tetrapyrrolic macrocycles.
  • To synthesize novel calix[4]pyrrole analogues and explore their structural characteristics.

Main Methods:

  • A two-step synthetic approach utilizing Grignard reagents.
  • Modification of tetrapyrrolic macrocycles by replacing methylene bridges with BCP units.
  • Characterization using single-crystal X-ray diffraction and 2D NMR spectroscopy.

Main Results:

  • Successful synthesis of versatile bicyclo[1.1.1]pentane (BCP) derivatives.
  • Formation of BCP-containing tetrapyrrolic macrocycles and new calix[4]pyrrole analogues.
  • Observation of a doubly N-confused system with electron-withdrawing substituents.
  • Determination of 1,3-alternate or αβαβ conformations in BCP-containing macrocycles via X-ray diffraction and NMR.

Conclusions:

  • The developed method provides a versatile platform for synthesizing BCP-functionalized macrocycles.
  • The study introduces a new class of calix[4]pyrrole analogues with potential applications.
  • The conformational flexibility of these novel macrocycles has been elucidated.