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Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions

Abstract

The crystal structures of five compounds capable of forming self-complementary hydrogen bonds but crystallizing as catemers or creating more complex crystal structures were compared with their complexes prepared by cocrystallization with perfluoroaryl compounds. The results of X-ray diffraction revealed that in all the cases the π–π stacking interactions caused reorganization of hydrogen bonds and induced creation of the expected self-complementary hydrogen bond dimeric motifs. The results point to the potential of aryl–perfluoroaryl interactions for the control of molecular self-assembly of aromatic compounds able to form hydrogen bonds. Also, the electrostatic potential (ESP) surfaces were investigated in terms of intermolecular interactions in the studied cocrystals. The values of the locally most negative and most positive ESP confirmed the best donor and acceptor sites for hydrogen bonding and other contacts.

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DOI:
Digital Object Identifier (open in new tab) 10.1021/acs.cgd.3c00676
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Category:
Articles
Type:
artykuły w czasopismach
Published in:
CRYSTAL GROWTH & DESIGN no. 23, pages 6830 - 6839,
ISSN: 1528-7483
Language:
English
Publication year:
2023
Bibliographic description:
Alfuth J., Kazimierczuk K., Połoński T., Olszewska T.: Intermolecular Hydrogen Bonding Directed by Aryl–Perfluoroaryl π–π Stacking Interactions// CRYSTAL GROWTH & DESIGN -,iss. 9 (2023), s.6830-6839
DOI:
Digital Object Identifier (open in new tab) 10.1021/acs.cgd.3c00676
Sources of funding:
  • COST_FREE
Verified by:
Gdańsk University of Technology

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