Citation: Haobo Ling,  Peihong Zhao,  Shouyun Yu. A Controversy in the Textbooks of Organic Chemistry: The Origin of the Stability of Ethane Conformations[J]. University Chemistry, ;2024, 39(1): 325-331. doi: 10.3866/PKU.DXHX202307060 shu

A Controversy in the Textbooks of Organic Chemistry: The Origin of the Stability of Ethane Conformations

  • The conformations of alkanes and their stability are important topics in basic organic chemistry. Among them, the staggered and eclipsed conformations of ethane are the most fundamental. Current undergraduate organic chemistry textbooks both domestically and internationally provide different explanations for the stability of the staggered conformation of ethane compared to the eclipsed conformation, leading to confusion and making it difficult for undergraduate teaching. In this study, we conducted a survey of literatures, organized different arguments and evidence for the stability of the staggered conformation of ethane, and pointed out the shortcomings of analysis and calculation methods in previous literatures. Through literature research, we believe that both hyperconjugation and steric hindrance should be included in the textbooks.
  • 加载中
    1. [1]

    2. [2]

    3. [3]

    4. [4]

    5. [5]

    6. [6]

    7. [7]

      Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, UK, 2012; p. 364.

    8. [8]

      Jones, M. Jr.; Fleming, S. A. Organic Chemistry, 4th ed.; W. W. Norton & Company: New York, USA, 2015, pp. 66–67.

    9. [9]

      Smith, J. G. Organic Chemistry, 3rd ed.; McGraw-Hill: New York, USA, 2011, p. 133.

    10. [10]

      Bruice, P. Y. Organic Chemistry, 8th ed.; Pearson: Boston, USA, 2015, pp. 119–120.

    11. [11]

      Pophristic, V.; Goodman, L. Nature 2001, 414, 565.

    12. [12]

    13. [13]

      Eyring, H. J. Am. Chem. Soc. 1932, 54, 3191.

    14. [14]

      Gorin, E.; Walter, J.; Eyring, H. J. Am. Chem. Soc. 1939, 61, 1876.

    15. [15]

      Mulliken, R. S. J. Chem. Phys. 1939, 7, 339.

    16. [16]

      Mulliken, R. S.; Rieke, C. A.; Brown, W. G. J. Am. Chem. Soc. 1941, 63, 41.

    17. [17]

      Lassettre, E. N.; Dean, L. B. J. Chem. Phys. 1949, 17, 317.

    18. [18]

      Oosterhoff, L. J. Discuss. Faraday Soc. 1951, 10, 79.

    19. [19]

      Eyring, H.; Stewart, G. H.; Smith, R. P. Proc. Natl. Acad. Sci. USA 1958, 44, 259.

    20. [20]

      Wyatt, R. E.; Parr, R. G. J. Chem. Phys. 1965, 43, S217.

    21. [21]

      Sovers, O. J.; Kern, C. W.; Pitzer, R. M.; Karplus, M. J. Chem. Phys. 1968, 49, 2592.

    22. [22]

      Lowe, J. P. J. Am. Chem. Soc. 1970, 92, 3799.

    23. [23]

      England, W.; Gordon, M. S. J. Am. Chem. Soc. 1971, 93, 4649.

    24. [24]

      Radom, L.; Hehre, W.; Pople, J. J. Am. Chem. Soc. 1972, 94, 2371.

    25. [25]

      Stevens, R. M.; Karplus, M. J. Am. Chem. Soc. 1972, 94, 5140.

    26. [26]

      Honegger, E. J. Mol. Struct.: THEOCHEM 1989, 187, 261.

    27. [27]

      Badenhoop, J. K.; Weinhold, F. Int. J. Quantum Chem. 1999, 72, 269.

    28. [28]

      Bickelhaupt, F. M.; Baerends, E. J. Angew. Chem. Int. Ed. 2003, 42, 4183.

    29. [29]

      Song, L.; Lin, Y.; Wu, W.; Zhang, Q.; Mo, Y. J. Phys. Chem. A 2005, 109, 2310.

    30. [30]

      Mo, Y.; Gao, J. Acc. Chem. Res. 2007, 40, 113.

    31. [31]

      Salter, E. A.; Wierzbicki, A. Struct. Chem. 2016, 27, 1501.

    32. [32]

      Li, Z.; Xu, T.; Früchtl, H.; van Mourik, T.; Kirk, S. R. Jenkins, S. Chem. Phys. Lett. 2022, 800, 139669.

    33. [33]

      Novoa, T.; Contreras-García, J.; Chaquin, P. Phys. Chem. Chem. Phys. 2023, 25, 4276.

    34. [34]

      Bickelhaupt, F. M.; DeKock, R. L.; Baerends, E. J. J. Am. Chem. Soc. 2002, 124, 1500.

  • 加载中
    1. [1]

      Jiaxi Xu Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049

    2. [2]

      Yaling Chen . Basic Theory and Competitive Exam Analysis of Dynamic Isotope Effect. University Chemistry, 2024, 39(8): 403-410. doi: 10.3866/PKU.DXHX202311093

    3. [3]

      YanYuan Jia Rong Rong Jie Liu Jing Guo GuoYu Jiang Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035

    4. [4]

      Xingyuan Lu Yutao Yao Junjing Gu Peifeng Su . Energy Decomposition Analysis and Its Application in the Many-Body Effect of Water Clusters. University Chemistry, 2025, 40(3): 100-107. doi: 10.12461/PKU.DXHX202405074

    5. [5]

      Supin Zhao Jing Xie . Understanding the Vibrational Stark Effect of Water Molecules Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 178-185. doi: 10.12461/PKU.DXHX202406024

    6. [6]

      Yaqin Zheng Lian Zhuo Meng Li Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119

    7. [7]

      Tianyun Chen Ruilin Xiao Xinsheng Gu Yunyi Shao Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

    8. [8]

      Lei FengZe-Min ZhuYing YangZongbin HeJiafeng ZouMan-Bo LiYan ZhaoZhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029

    9. [9]

      Xiaotian ZHUFangding HUANGWenchang ZHUJianqing ZHAO . Layered oxide cathode for sodium-ion batteries: Surface and interface modification and suppressed gas generation effect. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 254-266. doi: 10.11862/CJIC.20240260

    10. [10]

      Ying Zhang Fang Ge Zhimin Luo . AI-Driven Biochemical Teaching Research: Predicting the Functional Effects of Gene Mutations. University Chemistry, 2025, 40(3): 277-284. doi: 10.12461/PKU.DXHX202412104

    11. [11]

      Haiying Jiang Liuhong Song Yangyang Cheng Kefen Yue Mingli Peng Huilin Guo . Ph―C≡C―Cu2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003

    12. [12]

      Weikang WangYadong WuJianjun ZhangKai MengJinhe LiLele WangQinqin Liu . Green H2O2 synthesis via melamine-foam supported S-scheme Cd0.5Zn0.5In2S4/S-doped carbon nitride heterojunction: synergistic interfacial charge transfer and local photothermal effect. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-0. doi: 10.1016/j.actphy.2025.100093

    13. [13]

      Chao LiuHuan YuJiaming LiXi YuZhuangzhi YuYuxi SongFeng ZhangQinfang ZhangZhigang Zou . 具有光热效应的多级Ti3C2/Bi12O17Br2肖特基异质结简单合成及其太阳能驱动抗生素光降解的研究. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-0. doi: 10.1016/j.actphy.2025.100075

    14. [14]

      Mengfei HeChao ChenYue TangSi MengZunfa WangLiyu WangJiabao XingXinyu ZhangJiahui HuangJiangbo LuHongmei JingXiangyu LiuHua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 2310029-0. doi: 10.3866/PKU.WHXB202310029

    15. [15]

      Cheng PENGJianwei WEIYating CHENNan HUHui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs3Bi2X9 (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282

    16. [16]

      Yanglin JiangMingqing ChenMin LiangYige YaoYan ZhangPeng WangJianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027

    17. [17]

      Kexin DongChuqi ShenRuyu YanYanping LiuChunqiang ZhuangShijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag3PO4/C3N5 Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-0. doi: 10.3866/PKU.WHXB202310013

    18. [18]

      Shipeng WANGShangyu XIELuxian LIANGXuehong WANGJie WEIDeqiang WANG . Piezoelectric effect of Mn, Bi co-doped sodium niobate for promoting cell proliferation and bacteriostasis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1919-1931. doi: 10.11862/CJIC.20240094

    19. [19]

      Junjie Zhang Yue Wang Qiuhan Wu Ruquan Shen Han Liu Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084

    20. [20]

      Ran HUOZhaohui ZHANGXi SULong CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195

Metrics
  • PDF Downloads(3)
  • Abstract views(1318)
  • HTML views(99)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return