Separation of closely related structural isomers by inclusion complexation with tailor-made host compounds. Crystal structures of 2,2-di (p-hydroxyphenyl) propane and Its 1:1 complex withp-cresol |
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Authors: | Israel Goldberg Zafra Stein Koichi Tanaka Fumio Toda |
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Affiliation: | (1) School of Chemistry, Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv, 69978 Tel Aviv, Israel;(2) Department of Industrial Chemistry, Faculty of Engineering, Ehime University, 790 Matsuyama, Japan |
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Abstract: | The crystal structures of the 2,2-di(p-hydroxyphenyl)propane host and its 1:1 adducts withm-andp-cresol guests have been studied. The preferential complexation of this host withp-cresol overm-cresol is related to the opposite trend exhibited by 1,1-di(p-hydroxyphenyl)cyclohexane; both hosts can separate effectively the two cresols from their liquid mixture by crystalline inclusion. A plausible explanation of the different inclusion features is provided by examining the intermolecular association in the corresponding solids. The analysed structures are stabilized by strong and continuous H-bonding between the constituent entities along two dimensions, and by weak van der Waals forces along the third axis. The p-cresol complex of the title host reveals a unique arrangement within and a more efficient packing of the layered structure, and thus represents a more stable and less soluble crystal lattice than itsm-cresol analog.Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82099 (8 pages). |
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Keywords: | Isomeric separations by crystalline inclusion host design molecular recognition of alcohols |
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