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Inclusion of Caffeine by a Diol Host

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Abstract

The host compound 9,9′-(ethyne-1,2-diyl)-bis(fluoren-9-ol), H, forms inclusion compounds with caffeine (H·CAF) and methanol (H·MeOH). The host and guest ratios were 1:2 and 1:1, respectively. Both of these structures were successfully solved in P-1 with unit cell dimensions for H·CAF: a = 7.2121(14) Å, b = 9.2782(19) Å, c = 15.206(3) Å, α = 73.23(3)°, β = 84.20(3)°, γ = 73.39(3)°, Z = 2 and for H·MeOH : a = 9.7592(10) Å, b = 11.2584(11) Å, c = 20.7854(19) Å, α = 97.161(2)°, β = 99.263(2)°, γ = 95.257(2) Å, Z = 2. These crystal structures were studied together with that of a mixed clathrate, H·CAF·MeOH with stoichiometry 2:1:1.5. For H·CAF·MeOH which was solved in P21/c : a = 12.2051(5) Å, b = 46.8023(19) Å, c = 9.0121(4) Å, β = 91.9650(10)°, Z = 4. The kinetics of desolvation of the methanol solvate (H·MeOH) yielded an activation energy of 69.6–83.9 kJ mol−1.

Graphical Abstract

The diol host 9,9′-(ethyne-1,2-diyl)-bis(fluoren-9-ol) forms an inclusion compound with caffeine and methanol.

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Acknowledgments

We thank the CPUT and the NRF (Pretoria) for funding. CCDC 780740–780742 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44(0)1223-336033.

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Authors and Affiliations

  1. Department of Chemistry, Cape Peninsula University of Technology, Cape Town Campus, P.O. Box 652, Cape Town, 8000, South Africa

    Ayesha Jacobs, Luigi R. Nassimbeni, Kanyisa L. Nohako, Gaëlle Ramon & Baganetsi K. Sebogisi

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  1. Ayesha Jacobs
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  2. Luigi R. Nassimbeni
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  3. Kanyisa L. Nohako
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  4. Gaëlle Ramon
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  5. Baganetsi K. Sebogisi
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Correspondence to Ayesha Jacobs.

Additional information

The host compound 9,9′-(ethyne-1,2-diyl)-bis(fluoren-9-ol) forms inclusion compounds with caffeine (H·CAF) and methanol (H·MeOH). Both of these crystal structures were studied together with that of a mixed clathrate, H·CAF·MeOH. The kinetics of desolvation of the methanol solvate (H·MeOH) was determined.

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Jacobs, A., Nassimbeni, L.R., Nohako, K.L. et al. Inclusion of Caffeine by a Diol Host. J Chem Crystallogr 41, 610–616 (2011). https://doi.org/10.1007/s10870-010-9933-1

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  • DOI: https://doi.org/10.1007/s10870-010-9933-1

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