Multiple intermolecular interactions in guest inclusion by acyclic host compounds

Literature Information

Publication Date 2023-10-27
DOI 10.1039/D3CE00775H
Impact Factor 3.545
Authors

Masatoshi Kawahata, Haruka Yamamoto, Masahide Tominaga, Kentaro Yamaguchi


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Abstract

Disubstituted adamantanes having nitrophenol moieties were examined for their ability to recognize ketone and ester molecules through multiple intermolecular interactions, with the hydroxyl and nitro groups serving as hydrogen bond donors and acceptors. Crystallization of 1,3-bis(2-hydroxy-5-nitrophenyl)adamantane (1) in acetone, 2-butanone, and methyl acetate afforded three inclusion crystals with 1 : 1 stoichiometry. X-ray crystallographic analysis revealed that the hydroxyl groups of 1 engaged in OH⋯O interactions with the guest oxygen atoms in all crystals. Moreover, the guest hydrogen atoms participated in CH⋯O interactions with the host nitro and hydroxyl groups at three, four, or five points. These findings suggest that the guest molecules were captured through interactions with multiple functional groups in a manner resembling that of guest inclusion in enzyme pockets. Crystallization of 1,3-bis(4-hydroxy-3-nitrophenyl)adamantane (2) and 1,3-bis(2-ethoxy-5-nitrophenyl)adamantane (3) in acetone resulted in the formation of guest-free crystals, with NO2⋯NO2 interactions being prominent in the crystal of 3.

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CrystEngComm

CrystEngComm
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CrystEngComm is the forum for the design and understanding of crystalline materials. We welcome studies on the investigation of molecular behaviour within crystals, control of nucleation and crystal growth, engineering of crystal structures, and construction of crystalline materials with tuneable properties and functions. We publish hypothesis-driven research into… how crystal design affects thermodynamics, phase transitional behaviours, polymorphism, morphology control, solid state reactivity (crystal-crystal solution-crystal, and gas-crystal reactions), optoelectronics, ferroelectric materials, non-linear optics, molecular and bulk magnetism, conductivity and quantum computing, catalysis, absorption and desorption, and mechanical properties. Using Techniques and methods including… Single crystal and powder X-ray, electron, and neutron diffraction, solid-state spectroscopy, spectrometry, and microscopy, modelling and data mining, and empirical, semi-empirical and ab-initio theoretical evaluations. On crystalline and solid-state materials. We particularly welcome work on MOFs, coordination polymers, nanocrystals, host-guest and multi-component molecular materials. We also accept work on peptides and liquid crystals. All papers should involve the use or development of a design or optimisation strategy. Routine structural reports or crystal morphology descriptions, even when combined with an analysis of properties or potential applications, are generally considered to be outside the scope of the journal and are unlikely to be accepted.

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