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Rationalization of regioselectivity of electrophilic substitution reaction for cyclic compounds in terms of Dpb values

Yang Liu ,  Zhong-Zhi Yang ,  Dong-Xia Zhao

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Citation:  Yang Liu, Zhong-Zhi Yang, Dong-Xia Zhao. Rationalization of regioselectivity of electrophilic substitution reaction for cyclic compounds in terms of Dpb values[J]. Chinese Chemical Letters, 2015, 26(5): 553-556. doi: 10.1016/j.cclet.2014.12.013 shu

Rationalization of regioselectivity of electrophilic substitution reaction for cyclic compounds in terms of Dpb values

    • 通讯作者: Zhong-Zhi Yang,
    Dong-Xia Zhao,
  • 基金项目:

    as well as program for Liaoning Excellent Talents in University LNET (No. LJQ2013111) (No. LJQ2013111)

    Natural Science Foundation of Liaoning Province (No. 2014020150). (No. 2014020150)

摘要: Accepted theories predict that substitution reactions are controlled by the electronic nature of the attacked site for electrophilic aromatic substitution. Here it is shown that in addition the bond strength of the broken bond may also influence the regioselectivity of the substitution reaction, and that the Dpb is a good indicator of the strength of a chemical bond. The Dpb denotes the depth of the potential acting on one electron in amolecule at the bond center (bc). In this letter, the values of Dpb along the C-H and N-H bonds have been investigated, and it is demonstrated that for aromatic compounds, the regioselectivity of the electrophilic substitution can well be rationalized in terms of Dpb values.

English

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  • 发布日期:  2014-12-30
  • 收稿日期:  2014-09-25
  • 网络出版日期:  2014-12-15
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