## Calculation and Discussion of Some Questions in the Teaching of Aromatic Hydrocarbon Chapter

Wang Wenfeng,, Yuan Yaofeng, Lin Zhimin

 基金资助: 福建省自然科学基金资助.  2017J01578福州大学一流学科建设项目

Abstract

By means of calculation on the molecular structures and energies of some organic compounds and intermediates based on 6-311G(d)/B3LYP method, the following questions have been discussed:(1) regioselectivity of Birch reduction; (2) electronic effect of chloromethyl; (3) effect of antiaromaticity on structures of organic compounds; (4) local aromaticity of polycyclic compounds. These calculations and discussions enrich the teaching content of organic chemistry course and are useful for college students to study aromatic hydrocarbon.

Keywords： Aromatic hydrocarbon ; Computational chemistry ; Molecular structure ; Teaching content

Wang Wenfeng. Calculation and Discussion of Some Questions in the Teaching of Aromatic Hydrocarbon Chapter. University Chemistry[J], 2020, 35(7): 171-178 doi:10.3866/PKU.DXHX201910046

## 1 计算方法

### 图3

(a)环己二烯自由基和负离子共振结构；(b)环己二烯自由基HOMO轨道图；(c)环己二烯负离子HOMO轨道图

### 图5

#### 2.2.2 CH2Cl与苯环相连

CH2Cl与苯环相连时是给电子基还是吸电子基，这个问题在邢其毅版教科书中有确切答案[6]，即CH2Cl是弱钝化苯环的邻对位定位基。对CH2Cl如何钝化苯环，教科书中没有给予说明。本文计算了氯甲苯的分子结构，如图6所示。

### 图8

(a)化合物D (二偶联苯)的共振结构；(b)化合物E (二偶联环丁二烯)的共振结构；(c)化合物D优化后的分子结构；(d)化合物E优化后的分子结构

### 图9

(a)化合物F的共振结构；(b)化合物G的共振结构；(c)化合物F优化后分子结构；(d)化合物G优化后分子结构

## 参考文献 原文顺序 文献年度倒序 文中引用次数倒序 被引期刊影响因子

Vollhardt, P.; Schore, N. Organic Chemistry: Structure and Function, 6th ed.; W. H. Freeman and Company: New York, USA 2009.

Platt J. R. J. Chem. Phys. 1954, 22, 1448.

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