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DFT study on binding of single and double methane with aromatic hydrocarbons and graphene: stabilizing CH…HC interactions between two methane molecules

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Abstract

Density functional theory (DFT) calculations were used to examine the binding strength of one and two methane molecule(s) with graphene (62 and 186 carbon atoms) and model systems of aromatic hydrocarbons (benzene, pyrene, and coronene). We explored different possibilities of binding modes of methane such as one, two, and three C-H interacting with small π-systems. Two methane molecules were considered to bind from the same as well as opposite sides of the plane of benzene and other π-systems including graphene models. Our results show that methane molecule prefers to bind with three C-H…π interactions with all the π-systems except benzene. The preference of tripod configuration of methane on the surface of graphene systems strongly agrees with the neutron diffraction experiment of methane on graphitized carbon black. The binding strength is almost doubled by increasing the number of methane molecules from one to two. Importantly, two methane molecules prefer to bind on the same side rather than opposite sides of the plane of graphene due to stabilizing CH…HC interactions between them in addition to six C-H…π interactions. Interestingly, binding strength contributions from CH…HC interactions (approx. 0.4–0.5 kcal/mol) of two methane molecules on the surface are analogous to methane dimer complex free from the surface of graphene. C-H stretching frequency shifts, bond lengths, and binding distances support the presence of CH…HC interactions between two methane molecules. Structures of complexes, binding energies, and C-H stretching frequency shifts agree with available experimental data.

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Funding

TD recognizes the National Science Foundation (NSF) for the grants through HBCU-UP RIA (Grant Number: 1601071), HBCU-UP TIP (Grant Number: 1623287), and RISE (Grant Number: 1924204). Graduate Studies Office at Clark Atlanta University is thanked for the graduate student support to JL through Title III program. DD acknowledges Saudi Arabian Cultural Mission (SACM) for the scholarship. Extreme Science and Engineering Discovery Environment (XSEDE) is acknowledged for the computational resources (resource allocation grant DMR 160170).

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  1. Department of Chemistry, Clark Atlanta University, 223 James P. Brawley Drive, S.W, Atlanta, GA, 30314, USA

    Jovian Lazare, Dalia Daggag & Tandabany Dinadayalane

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  1. Jovian Lazare
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The top and/or side views along with BSSE corrected and uncorrected binding energies, and M06-2X/6-31G(d) level optimized Cartesian coordinates of all molecules and/or complexes considered, selected C-H stretching frequencies and their intensities, data for methane dimer complex are provided. The Supporting Information is available free of charge at https://www.springer.com/ (PDF 7409 kb)

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Lazare, J., Daggag, D. & Dinadayalane, T. DFT study on binding of single and double methane with aromatic hydrocarbons and graphene: stabilizing CH…HC interactions between two methane molecules. Struct Chem 32, 591–605 (2021). https://doi.org/10.1007/s11224-020-01657-y

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