Hydrogen Bonding versus Halogen Bonding in Host–Guest Compounds

The similarity and differences of the three host compounds H1 = 9,9′-(biphenyl-2,2′-diyl)­difluoren-9-ol, H2 = 2,2′,7,7′-tetrabromo-9,9′-(biphenyl-2,2′-diyl)­difluoren-9-ol, and H3 = 2,2′,7,7′-tetra-tert-butyl-9,9′-(1,4-phenylene)­difluoren-9-ol which form inclusion compounds with 3-bromopyridine an...

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Bibliographic Details
Published in:Crystal growth & design 2016-08, Vol.16 (8), p.4765-4771
Main Authors: Amombo Noa, Francoise M, Bourne, Susan A, Su, Hong, Weber, Edwin, Nassimbeni, Luigi R
Format: Article
Language:English
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Summary:The similarity and differences of the three host compounds H1 = 9,9′-(biphenyl-2,2′-diyl)­difluoren-9-ol, H2 = 2,2′,7,7′-tetrabromo-9,9′-(biphenyl-2,2′-diyl)­difluoren-9-ol, and H3 = 2,2′,7,7′-tetra-tert-butyl-9,9′-(1,4-phenylene)­difluoren-9-ol which form inclusion compounds with 3-bromopyridine and its chloro-analogue guest are compared with respect to hydrogen bonding and halogen bonding. In all cases the hydrogen bonding motif (Host)­O–H···O­(Host)–H···N­(Guest) predominates while the halogen···halogen interactions are of secondary importance in the packing of the structures. The structural data are supported by thermal analysis, Hirshfeld surface analysis, and IR spectroscopy.
ISSN:1528-7483
1528-7505
DOI:10.1021/acs.cgd.6b00886