Citation: Tianqi Sheng, Xuenan Yang, Zhaoyang Li, Shaoguang Zhang. Understanding structural influences in organoelement compounds through configurational inversion of amines, phosphines, and sulfoxides[J]. University Chemistry, ;2026, 41(7): 415-429. doi: 10.12461/PKU.DXHX202505012 shu

Understanding structural influences in organoelement compounds through configurational inversion of amines, phosphines, and sulfoxides

1.
Tanwei College, Tsinghua University, Beijing 100084, China;
2.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

Corresponding author: Shaoguang Zhang, sgzhang@mail.tsinghua.edu.cn
Received Date: 8 May 2025
Revised Date: 31 July 2025

Although nitrogen (amine), phosphorus (phosphine), and sulfur (sulfoxide) centered chiral compounds all adopt sp³-hybridized configurations, they demonstrate markedly different energy barriers and rates for configurational inversion, resulting in varying degrees of difficulty in chiral isomer separation. Using these three compound classes as representative examples, this study systematically examines the key factors governing inversion barriers. The analysis reveals that the fundamental distinction originates from the inherent properties of the central atoms, thereby illustrating the foundational principle of organoelement chemistry that “elemental characteristics determine structural and reactivity features”. This work aims to help students develop an electron structure-based approach for understanding structure-reactivity relationships.
- Chiral amines,
- Chiral phosphines,
- Chiral sulfoxides,
- Configuration inversion,
- Organoelement chemistry
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沈阳化工大学材料科学与工程学院沈阳 110142