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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.6K
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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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.2K
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,...
5.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
3.5K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.8K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
11.8K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

12.6K
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 +...
12.6K
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

21.5K
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and...
21.5K

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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7つの六角形環からなるジフェナレンについて

Oliwier Misztal1, Sławomir Ostrowski1, Jan Cz Dobrowolski1

  • 1Institute of Nuclear Chemistry and Technology, 16 Dorodna-Street, 03-195 Warsaw, Poland.

ACS omega
|December 22, 2025
PubMed
まとめ

複雑な炭化水素であるジフェナレンは、一重項状態と三重項状態で異なる安定性を示す。その芳香族性と構造は基底状態の予測に影響を与え、安定性と芳香族性に関する一般的な仮定に疑問を投げかける。

科学分野:

  • 有機化学
  • 計算化学
  • 材料科学

背景:

  • ジフェナレンは、2つのフェナレンユニットから構成される多環芳香族炭化水素である。
  • それらの電子的特性と安定性を理解することは、新しい有機材料を設計するために重要である。
  • 以前の研究では、いくつかのジフェナレン誘導体の合成と基本的な特性が検討されている。

研究 の 目的:

  • 様々なジフェナレン構造の基底状態(一重項 vs 三重項)を調査する。
  • 分子構造、芳香族性、電子的安定性の関係を分析する。
  • 構造モチーフに基づいてジフェナレンの基底状態を予測するモデルを開発する。

主な方法:

  • cc-pVTZ基底セットを用いた密度汎関数理論(DFT)計算を採用した。
  • 一重項-三重項エネルギーギャップ、ギブズ自由エネルギー差、調和振動数の解析。
  • HOMAおよびINICS指数を用いた芳香族性の評価。

主要な成果:

  • 研究対象の8つのジフェナレンのうち4つは一重項状態を好み、4つは三重項状態を好む。
  • 一重項-三重項ギャップは一般的に10 kcal/molを超え、2つの例外は約5 kcal/molである。
キーワード:
ジフェナレン多環芳香族炭化水素基底状態安定性芳香族性密度汎関数理論

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  • 安定した一重項状態の分子では、典型的な安定性の仮定とは対照的に、芳香族性が著しく低下する。
  • 結論:

    • ジフェナレンの安定性は構造的特徴に影響され、スピンパターンの解析によって予測できる。
    • 一重項状態における芳香族性と安定性の逆相関は、従来の理解に疑問を投げかける。
    • この研究は、複雑な多環芳香族炭化水素の電子的挙動に関する洞察を提供する。