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T-shaped phenol–benzene complexation driven by π-involved noncovalent interactions

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Abstract

Intermolecular interactions between phenol and benzene molecules with the T-shaped geometries could be diverse. They can be pursued via two structural series: one with benzene standing above phenol using one or two C–H bonds as the anchoring point and the other with phenol standing on top of benzene with either C–H or O–H bond as the leg. In this work, structure and interaction properties of these species are investigated at the DFT M06-2X/6-311++G(2d,2p) level of theory without and with the counterpoise correction. A total of twelve distinct isomers have been identified, eight of which were unveiled for the first time. It is found that π–π interactions play essential roles in stabilizing these conformations, while C–H/π, C–H···O van der Waals interactions, and C–H···O and O–H/π hydrogen bonds are also involved and positively contribute to the stability of these species. Our energy decomposition analysis shows that the driving force for the formation of these complexes arises from attractive electrostatic, exchange, polarization, and dispersion terms, balanced by the repulsion term. The dispersion effect plays a dominant role, but the electrostatic and exchange terms are also markedly significant. Their close relationships between one another have also been disclosed.

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Acknowledgments

The work was financially supported by the National Natural Science Foundation of China (Grant No. 21403097) and the Fundamental Research Funds for the Central Universities (lzujbky-2014-182).

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Authors and Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, 730000, Lanzhou, People’s Republic of China

    Pan-Pan Zhou, Xing Yang & Da-Gang Zhou

  2. Research Computing Center, University of North Carolina, Chapel Hill, NC, 27599, USA

    Shubin Liu

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  1. Pan-Pan Zhou
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  2. Xing Yang
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  3. Da-Gang Zhou
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  4. Shubin Liu
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Correspondence to Pan-Pan Zhou or Shubin Liu.

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Published as part of the special collection of articles “Festschrift in honour of A. Vela”.

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Zhou, PP., Yang, X., Zhou, DG. et al. T-shaped phenol–benzene complexation driven by π-involved noncovalent interactions. Theor Chem Acc 135, 100 (2016). https://doi.org/10.1007/s00214-016-1863-3

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