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Discovery of σ-hole interactions involving ylides

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Abstract

The positive electrostatic potentials (σ-hole) have been found in ylides CH2XH3 (X = P, As, Sb) and CH2YH2 (Y = S, Se, Te), on the outer surfaces of group VA and VIA atoms, approximately along the extensions of the C–X and C–Y bonds, respectively. These electrostatic potentials suggest that the above ylides can interact with nucleophiles to form weak, directional noncovalent interactions similar to halogen bonding interactions. MP2 calculations have confirmed the formation of CH2XH3···HM complexes (X = P, As, Sb; M = BeH, ZnH, MgH, Li, Na). The interaction energies, interaction distances, topological properties (electron density and its Laplacian), and energy properties (kinetic electron energy density and potential electron energy density) at the X(1)···H(10) bond critical points are all correlated with the most negative electrostatic potential value of HM, indicating that electrostatic interactions play an important role in these weak X···H interactions. Similar to the halogen bonding interactions, weak interactions involving ylides may be significant in several areas such as organic synthesis, crystal engineering, and design of new materials.

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Acknowledgments

Thanks for International Science Editing to edit this paper. This project was supported by the National Natural Science Foundation of China (Contract Nos.: 21371045, 21102033, 21171047, 21073051), the Natural Science Foundation of Hebei Province (Contract No.: B2011205058), and the Education Department Foundation of Hebei Province (ZH2012106, ZD2010126).

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Authors and Affiliations

  1. College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang, 050024, China

    Jiannan Ji, Yanli Zeng, Xueying Zhang, Shijun Zheng & Lingpeng Meng

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  1. Jiannan Ji
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  2. Yanli Zeng
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  3. Xueying Zhang
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  4. Shijun Zheng
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  5. Lingpeng Meng
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Correspondence to Yanli Zeng or Lingpeng Meng.

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Ji, J., Zeng, Y., Zhang, X. et al. Discovery of σ-hole interactions involving ylides. J Mol Model 19, 4887–4895 (2013). https://doi.org/10.1007/s00894-013-1992-8

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  • DOI: https://doi.org/10.1007/s00894-013-1992-8

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