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The competition of C-X⋯O=P halogen bond and π-hole⋯O=P bond between halopentafluorobenzenes C6F5X (X=F, Cl, Br, I) and triethylphosphine oxide

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Abstract

Calculation predicted the interacting forms of halopentafluorobenzene C6F5X (X=F, Cl, Br, I) with triethylphosphine oxide which is biologically interested and easily detected by 31P NMR. The interaction energy and geometric parameters of resultant halogen or π-hole bonding complexes were estimated and compared. Moreover, the bonding constants were determined by 31P NMR. Both theory and experiments indicated the C6F6 and C6F5Cl interact with triethylphosphine oxide by π-hole bonding pattern, while C6F5I by halogen/σ-hole bonding form. For C6F5Br, two interactions are comparative and should coexist competitively. The calculated interaction energies of σ-hole bonding complexes, −5.07 kcal mol−1 for C6F5Br⋯O=P and −8.25 kcal mol−1 for C6F5I⋯O=P, and π-hole bonding complexes, −7.29 kcal mol−1 for C6F6⋯O=P and −7.24 kcal mol−1 for C6F5Cl⋯O=P, are consistent with the changing tendency of bonding constants measured by 31P NMR, 4.37, 19.7, 2.42 and 2.23 M−1, respectively.

The competitive σ-hole···O=P and π-hole···O=P bonds between C6F5X (X=F, Cl, Br, I) and O=PEt3

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Acknowledgments

Financial supports from the National Natural Science Foundation of China (No.90922023), Ph. D foundation program of Ministry of Education (No.20110003110011) are gratefully acknowledged. We also appreciate very much the reviewers and editor’s valuable suggestions and advice on this paper.

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Authors and Affiliations

  1. College of Chemistry, Beijing Normal University, Beijing, 100875, The People’s Republic of China

    Xiao Ran Zhao, Hui Wang & Wei Jun Jin

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  1. Xiao Ran Zhao
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  2. Hui Wang
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  3. Wei Jun Jin
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Correspondence to Wei Jun Jin.

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Zhao, X.R., Wang, H. & Jin, W.J. The competition of C-X⋯O=P halogen bond and π-hole⋯O=P bond between halopentafluorobenzenes C6F5X (X=F, Cl, Br, I) and triethylphosphine oxide. J Mol Model 19, 5007–5014 (2013). https://doi.org/10.1007/s00894-013-2007-5

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  • DOI: https://doi.org/10.1007/s00894-013-2007-5

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