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Layered, Two-Dimensional Hydrogen Bonding Nets in the Structure of the 1:1 Encounter Complex TMTTF–TCNB: Combined Structural and Spectroscopic Study

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Abstract

The synthesis, crystal structure and spectroscopic properties as determined by infrared spectroscopy of the 1:1 encounter complex TMTTF–TCNB are reported. The complex crystallizes with each of the constituent molecules on an inversion center in the triclinic space group P − 1 with a = 6.7953(16) Å, b = 7.9141(16) Å, c = 9.775(2) Å, α = 98.63(3)°, β = 105.27(3)°, and γ = 94.49(3)°. The determination of this crystal structure provided cyanide bond distances which when compared to the reported literature values for free TCNB suggest the presence of the neutral acceptor. The central C=C bond and four ancillary C–S bonds in TMTTF provide structural evidence that the donor, like the acceptor, also exists in its neutral state. These crystallographic observations and conclusions were confirmed by infrared spectroscopic analysis. Of particular interest is a two dimensional hydrogen bonding net which occurs within the (\(13\bar{1}\)) plane. When stacked as repeat units along the a axis, this net is reminiscent of stacked graphene layers in graphite.

Graphical Abstract

The synthesis, crystal structure and spectroscopic properties as determined by infrared spectroscopy of the 1:1 encounter complex TMTTF-TCNB are reported. The complex crystallizes with each of the constituent molecules on an inversion center in the triclinic space group P − 1 with a = 6.7953(16) Å, b = 7.9141(16) Å, c = 9.775(2) Å, α = 98.63(3)°, β = 105.27(3)°, and γ = 94.49(3)°. The determination of this crystal structure provided cyanide bond distances which when compared to the reported literature values for free TCNB suggest the presence of the neutral acceptor. Of particular interest is a two dimensional hydrogen bonding net which occurs within the (\(13\bar{1}\)) plane. When stacked as repeat units along the a axis, this net is reminiscent of stacked graphene layers in graphite.

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Acknowledgments

This work was supported by The Welch Foundation (Grant A-1449) and the U.S. Department of Energy (Grant DE-FG01-05ER05-01). We also acknowledge the National Science Foundation (Grant 9807975) for the funds to purchase the X-ray diffractometer. EWR would like to sincerely thank Nancy Erskine for additional editorial assistance.

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  1. Eric W. Reinheimer

    Present address: Department of Chemistry, California State Polytechnic University, 3801 W. Temple Ave., Pomona, CA, 91768, USA

  2. Maria Fernandez Ballesteros Rivas

    Present address: Departmento de Química, Universidad Nacional Autónoma de Mexico, Circuito Exterior, Ciudad Universitaria, 04510, Coyoacan, DF, Mexico

Authors and Affiliations

  1. Department of Chemistry, Texas A&M University, College Station, TX, 77842-3012, USA

    Eric W. Reinheimer, Maria Fernandez Ballesteros Rivas, Hanhua Zhao & Kim R. Dunbar

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  1. Eric W. Reinheimer
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Correspondence to Eric W. Reinheimer.

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Reinheimer, E.W., Rivas, M.F.B., Zhao, H. et al. Layered, Two-Dimensional Hydrogen Bonding Nets in the Structure of the 1:1 Encounter Complex TMTTF–TCNB: Combined Structural and Spectroscopic Study. J Chem Crystallogr 41, 936–943 (2011). https://doi.org/10.1007/s10870-011-0021-y

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