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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...
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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 was based on the...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
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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Updated: Jun 28, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

構成的に安定した縦に曲がったポリサイクリック芳香化合物.

Robert S Walters1, Christina M Kraml, Neal Byrne

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|November 13, 2008
PubMed
まとめ
この要約は機械生成です。

研究者は,安定した,歪んだ多循環性芳香化合物を合成するための新しい方法を開発しました. これらの化合物は,円形の偏光光を含むユニークな光学特性を持ち,先進的な材料での潜在的な応用がある.

さらに関連する動画

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

関連する実験動画

Last Updated: Jun 28, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • マテリアルサイエンス 材料科学
  • スペクトロスコーピーは,スペクトロスコーピーを用います.

背景:

  • 構成的に安定したツィートポリサイクリック芳香化合物 (PAC) の開発は困難です.
  • 曲がる方向を制御し,安定したキラル形状を達成することは,それらの光学特性にとって極めて重要です.

研究 の 目的:

  • 2つの異なる戦略を使用して,構成的に安定した歪んだPACを合成する.
  • これらの新種のねじれたPACとその金属複合体のエナティオメールを分解し,特徴づけること.

主な方法:

  • ナフチル基を非対称に置換したPACの合成.
  • 準備型超臨界流体クロマトグラフィ (SFC) と高性能液体クロマトグラフィ (HPLC) を使用したイソメアのキラル分離.
  • 計算研究とスペクトロスコピク分析 (円形の二重化,円形の偏光光).

主要な成果:

  • 2,3-Bis(1-ナフチル) -1,4-ディフェニルトリフェニレン (7) と10-(1-ナフチル) -9,11,12,14-テトラフェニルベンゾ[b]トリフェニレン (13) などの歪んだPACのエナティオメールを成功して合成および分解しました.
  • 7 に対して適度に大きな特定の回転,13 に対して予想外にも小さな回転が観察され,コンフォーメーションの計算分析によって説明されました.
  • クイラルイリジウム (III) 複合体 (4) を,歪んだリガンドで作製し,構成的には安定していたが,溶解性の問題により,準備的に解消することが困難であった.

結論:

  • 開発された合成戦略は,構成的に安定した,歪んだPACとそのキラル派生体の作成を可能にします.
  • これらの化合物は,円形の二重化と円形の偏光光を含む重要なカイロプティカル特性を示す.
  • 特定の金属複合体の予備分解のための溶解性の制限を克服するために,さらなる研究が必要である.