环辛四烯的结构、芳香性及其异构化反应

doi:10.3866/PKU.DXHX202306006

Abstract

Abstract:

Cyclooctatetraene is a cyclic polyene composed of eight sp² carbon atoms. Understanding its structure and properties involves the application of various fundamental chemical theories and concepts. This article guides undergraduate students to use computational chemistry methods to investigate the electronic structure, geometric configuration, aromaticity, and isomerization reactions of cyclooctatetraene, with the aim of helping students achieve the following learning objectives: 1) understand the scientific concept that structure determines properties and properties respond to structure; 2) understand the limitation of the Hückel molecular orbital method (HMO) in dealing with 4n-type π-electron systems; 3) distinguish fundamental concepts such as aromaticity, antiaromaticity, and non-aromaticity and comprehend the Hückel's rule for determining the aromaticity of the ground state (singlet state) of a conjugated π-electron system, as well as the Baird's rule for determining the aromaticity of excited states (triplet state); and 4) clearly recognize that computational chemistry methods are essential tools for understanding the structure and properties of materials.

Key words: Cyclooctatetraene, HMO method, Aromaticity, Quantum chemistry calculations

Wei Fan, Xuqing Qian, Yuxuan Wang, Jialu Yang, Sunqiujun Zhang, Xinning Wang, Junxiao Han, Chenglong Lu, Dongju Zhang. Structure, Aromaticity, and Isomerization Reactions of Cyclooctetraene[J].University Chemistry, 2024, 39(1): 351-358.

Figures/Tables 5

References 34

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Structure, Aromaticity, and Isomerization Reactions of Cyclooctetraene

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