Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors
A series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted rea...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/1/163 |
| _version_ | 1819086929879105536 |
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| author | Stefan N. L. Andree Abhijeet S. Sinha Christer B. Aakeröy |
| author_facet | Stefan N. L. Andree Abhijeet S. Sinha Christer B. Aakeröy |
| author_sort | Stefan N. L. Andree |
| collection | DOAJ |
| description | A series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted reactions produced a co-crystal as indicated by IR spectroscopy. Four new crystal structures are reported and in all of them, at least one potential binding site on the acceptor is left vacant. The absence of halogen bonds to all sites can be ascribed primarily due to deactivation of the σ-hole on the iodo-arene donors and partially due to steric hindrance. The tritopic acceptors containing 5,6-dimethylbenzimidazole derivatives yield discrete tetrameric aggregates in the solid state, whereas the pyrazole and imidazole analogues assemble into halogen-bonded 1-D chains. |
| first_indexed | 2024-12-21T21:28:04Z |
| format | Article |
| id | doaj.art-9279abdd335c4e9da94f00cc6c829285 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T21:28:04Z |
| publishDate | 2018-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9279abdd335c4e9da94f00cc6c8292852022-12-21T18:49:42ZengMDPI AGMolecules1420-30492018-01-0123116310.3390/molecules23010163molecules23010163Structural Examination of Halogen-Bonded Co-Crystals of Tritopic AcceptorsStefan N. L. Andree0Abhijeet S. Sinha1Christer B. Aakeröy2Department of Chemistry, Kansas State University, Manhattan, KS 66506, USADepartment of Chemistry, Kansas State University, Manhattan, KS 66506, USADepartment of Chemistry, Kansas State University, Manhattan, KS 66506, USAA series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted reactions produced a co-crystal as indicated by IR spectroscopy. Four new crystal structures are reported and in all of them, at least one potential binding site on the acceptor is left vacant. The absence of halogen bonds to all sites can be ascribed primarily due to deactivation of the σ-hole on the iodo-arene donors and partially due to steric hindrance. The tritopic acceptors containing 5,6-dimethylbenzimidazole derivatives yield discrete tetrameric aggregates in the solid state, whereas the pyrazole and imidazole analogues assemble into halogen-bonded 1-D chains.http://www.mdpi.com/1420-3049/23/1/163halogen bondσ-holetritopic acceptorco-crystalscrystal structures |
| spellingShingle | Stefan N. L. Andree Abhijeet S. Sinha Christer B. Aakeröy Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors Molecules halogen bond σ-hole tritopic acceptor co-crystals crystal structures |
| title | Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors |
| title_full | Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors |
| title_fullStr | Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors |
| title_full_unstemmed | Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors |
| title_short | Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors |
| title_sort | structural examination of halogen bonded co crystals of tritopic acceptors |
| topic | halogen bond σ-hole tritopic acceptor co-crystals crystal structures |
| url | http://www.mdpi.com/1420-3049/23/1/163 |
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