环辛四烯的结构、芳香性及其异构化反应

引用本文: 凡维, 钱旭清, 王宇轩, 杨佳璐, 张孙秋骏, 王信凝, 韩俊骁, 鹿成龙, 张冬菊. 环辛四烯的结构、芳香性及其异构化反应[J]. 大学化学, 2024, 39(1): 351-358. doi: 10.3866/PKU.DXHX202306006 shu

Citation: 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. doi: 10.3866/PKU.DXHX202306006 shu

环辛四烯的结构、芳香性及其异构化反应

山东大学化学与化工学院, 济南 250100

通讯作者: 张冬菊,Email:zhangdj@sdu.edu.cn

基金项目:
国家自然科学基金（22273051，21833004）；山东省高等教育本科教学改革研究项目（Z2022169）；山东大学教育教学改革研究项目（2022Y072）；2022年山东大学研究生教育优质课程建设项目

摘要: 环辛四烯为八个sp²碳原子构成的环状轮烯，对其结构和性能的理解涉及一系列化学基本理论和基本概念的应用。本文通过本科生创新实验指导学生用计算化学方法研究了环辛四烯的电子结构、几何构型、芳香性、异构化反应等内容，以期引导学生达成如下学习目标：1）充分认识结构决定性能、性能反映结构的科学思想；2）了解Hückel分子轨道法（HMO）处理4n型π电子体系的局限性；3）区分芳香性、反芳香性和非芳香性等基本概念，理解判定共轭π电子体系基态（单重态）芳香性的Hückel规则以及激发态（三重态）芳香性的Baird规则；4）明确计算化学方法是理解物质结构和性能的重要手段。

关键词:

English

Structure, Aromaticity, and Isomerization Reactions of Cyclooctetraene

School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China

Corresponding author: Dongju Zhang, zhangdj@sdu.edu.cn

Received Date: 02 June 2023

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:

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

环辛四烯的结构、芳香性及其异构化反应

通讯作者: 张冬菊,Email:zhangdj@sdu.edu.cn

English

Structure, Aromaticity, and Isomerization Reactions of Cyclooctetraene

Corresponding author: Dongju Zhang, zhangdj@sdu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

环辛四烯的结构、芳香性及其异构化反应

通讯作者: 张冬菊,Email:zhangdj@sdu.edu.cn

English

Structure, Aromaticity, and Isomerization Reactions of Cyclooctetraene

Corresponding author: Dongju Zhang, zhangdj@sdu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

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