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Insights into the reaction mechanism between propadienylidene and ethylene: a DFT study

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Abstract

The reaction mechanism between propadienylidene and ethylene has been systematically investigated employing the B3LYP/6-311++G** and MP2/cc-pVTZ levels of theory to better understand the reactivity of propadienylidene with unsaturated hydrocarbons. Geometry optimization, vibrational analysis, and energy property for the involved stationary points on the potential energy surface have been calculated. Two important initial reaction complexes characterized by three- and four-membered ring structures have been located firstly. After that, three different products possessing three-, four-, and five-membered ring characters have been obtained through three reaction pathways. In the first reaction pathway, a three-membered ring alkyne compound has been obtained. As for the second reaction pathway, it is a diffusion-controlled reaction, resulting in the formation of the four-membered ring conjugated diene compound. A five-membered conjugated diene compound has been obtained in the third reaction pathway, which is the most stable product in the available products thermodynamically. On the other hand, the second reaction pathway is the most favorable reaction to proceed kinetically.

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Acknowledgment

This work is supported by NSFC (21003082, 31070046), the Project of Shandong Province Higher Educational Science and Technology Program (J09LB01, J09LB17), and the Foundation for Outstanding Young Scientist in Shandong Province (BS2009HZ014, BS2010NJ009). We are also grateful to the reviewers for their insightful suggestions to improve the presentation of the results.

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Authors and Affiliations

  1. College of Medical and Life Science, University of Jinan, Jinan, 250022, Shandong, People’s Republic of China

    Xiaojun Tan, Shankui Liu, Fang Wang & Hailong Wang

  2. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, Shandong, People’s Republic of China

    Ping Li & Weihua Wang

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  1. Xiaojun Tan
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  2. Ping Li
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  3. Weihua Wang
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  4. Shankui Liu
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Correspondence to Xiaojun Tan or Ping Li.

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Tan, X., Li, P., Wang, W. et al. Insights into the reaction mechanism between propadienylidene and ethylene: a DFT study. Struct Chem 22, 1031–1037 (2011). https://doi.org/10.1007/s11224-011-9798-8

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  • DOI: https://doi.org/10.1007/s11224-011-9798-8

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