争议中的两种“半椅式”结构——如何讲授环己烷构象翻转过程  

Two “Half-Chair” Structures in Controversy: How to Teach the Process of Conformations Interconvert of Cyclohexane

作　　者：郑素娟 张思翰 张凯瑞 赵健坤 石一锐 王佰全[1] 彭谦 ZHENG Su-Juan;ZHANG Si-Han;ZHANG Kai-Rui;ZHAO Jian-Kun;SHI Yi-Rui;WANG Bai-Quan;PENG Qian(State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China)

机构地区：[1]南开大学化学学院元素有机国家重点实验室南开大学有机新物质创造前沿科学中心,天津300071

出　　处：《化学教育（中英文）》2021年第18期130-133,共4页Chinese Journal of Chemical Education

基　　金：南开大学有机新物质创造前沿科学中心专项资金资助(63181206)。

摘　　要：环己烷的构象翻转问题是有机化学教学中重要的立体化学内容。虽然诸多中英文教材均指出环己烷构象翻转过程中存在着五碳共平面的半椅式构象,但是这种描述缺乏理论和实验的证据支撑。建议采用四碳共面的结构讲授环己烷构象翻转过程。该四碳共面构象不仅得到理论计算支撑,而且符合势能面的物理化学原理,但遗憾的是目前仅有少量教材使用这一表述。The issue of conformations interconvert in cyclohexane is important in stereochemistry for organic chemistry teaching. Although many Chinese and English textbooks describe that there are five coplanar carbon half-chair conformers in cyclohexane conformations interconvert, this description is lack of theoretical and experimental evidence. We suggest that four coplanar carbon structure should be used to describe the conformation interconvert process of cyclohexane. The four coplanar carbon conformer is not only supported by theoretical calculation, but also conforms to the physicochemical principles of potential energy surface. Unfortunately, only few textbooks use the proper expression at present.

关 键 词：环己烷结构 半椅式构象 有机立体化学 教育教学 

分 类 号：O624.11-4[理学—有机化学] G642[理学—化学]