Experimental and Theoretical Study of Halogen-Bonded Complexes of DMAP with Di- and Triiodofluorobenzenes. A Complex with a Very Short N···I Halogen Bond
X-ray single crystal structures are reported for 2:1 halogen-bonded complexes of 4-(N,N-dimethylamino)pyridine (DMAP) with 1,4- and 1,3-diiodotetrafluorobenzene and 1,3-diiodo-4,5,6-trifluorobenzene and for a 3:1 complex of DMAP with 1,3,5-triiodotrifluorobenzene. The complex between DMAP and 1,4-di...
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| Veröffentlicht in: | Crystal growth & design 2010-08, Vol.10 (8), p.3710-3720 |
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| container_title | Crystal growth & design |
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| creator | Roper, Laila C Präsang, Carsten Kozhevnikov, Valery N Whitwood, Adrian C Karadakov, Peter B Bruce, Duncan W |
| description | X-ray single crystal structures are reported for 2:1 halogen-bonded complexes of 4-(N,N-dimethylamino)pyridine (DMAP) with 1,4- and 1,3-diiodotetrafluorobenzene and 1,3-diiodo-4,5,6-trifluorobenzene and for a 3:1 complex of DMAP with 1,3,5-triiodotrifluorobenzene. The complex between DMAP and 1,4-diiodotetrafluorobenzene shows the shortest halogen bond recorded for fluorinated iodoarenes. Model systems based on complexes between the same iodofluorobenzenes and ammonia are investigated by Hartree−Fock and DFT calculations to gain insights into the features of halogen bonding in di- and triiodo systems. The calculations reveal a weak charge-transfer component to the halogen bond and account for the lengthening of the C−I bond on complexation in terms of the C−I antibonding character observed within the localized molecular orbital describing the N···I bond. |
| doi_str_mv | 10.1021/cg100549u |
| format | Article |
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A Complex with a Very Short N···I Halogen Bond</title><source>American Chemical Society Journals</source><creator>Roper, Laila C ; Präsang, Carsten ; Kozhevnikov, Valery N ; Whitwood, Adrian C ; Karadakov, Peter B ; Bruce, Duncan W</creator><creatorcontrib>Roper, Laila C ; Präsang, Carsten ; Kozhevnikov, Valery N ; Whitwood, Adrian C ; Karadakov, Peter B ; Bruce, Duncan W</creatorcontrib><description>X-ray single crystal structures are reported for 2:1 halogen-bonded complexes of 4-(N,N-dimethylamino)pyridine (DMAP) with 1,4- and 1,3-diiodotetrafluorobenzene and 1,3-diiodo-4,5,6-trifluorobenzene and for a 3:1 complex of DMAP with 1,3,5-triiodotrifluorobenzene. The complex between DMAP and 1,4-diiodotetrafluorobenzene shows the shortest halogen bond recorded for fluorinated iodoarenes. Model systems based on complexes between the same iodofluorobenzenes and ammonia are investigated by Hartree−Fock and DFT calculations to gain insights into the features of halogen bonding in di- and triiodo systems. The calculations reveal a weak charge-transfer component to the halogen bond and account for the lengthening of the C−I bond on complexation in terms of the C−I antibonding character observed within the localized molecular orbital describing the N···I bond.</description><identifier>ISSN: 1528-7483</identifier><identifier>EISSN: 1528-7505</identifier><identifier>DOI: 10.1021/cg100549u</identifier><language>eng</language><publisher>Washington,DC: American Chemical Society</publisher><subject>Condensed matter: electronic structure, electrical, magnetic, and optical properties ; Condensed matter: structure, mechanical and thermal properties ; Electron states ; Exact sciences and technology ; Methods of electronic structure calculations ; Physics ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Crystal growth & design, 2010-08, Vol.10 (8), p.3710-3720</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a204t-9dc935096a759ae82e0a729ec87a62ec9db6d8109ed6f0ce9e26588fd5bdacb63</citedby><cites>FETCH-LOGICAL-a204t-9dc935096a759ae82e0a729ec87a62ec9db6d8109ed6f0ce9e26588fd5bdacb63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/cg100549u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/cg100549u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23084305$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Roper, Laila C</creatorcontrib><creatorcontrib>Präsang, Carsten</creatorcontrib><creatorcontrib>Kozhevnikov, Valery N</creatorcontrib><creatorcontrib>Whitwood, Adrian C</creatorcontrib><creatorcontrib>Karadakov, Peter B</creatorcontrib><creatorcontrib>Bruce, Duncan W</creatorcontrib><title>Experimental and Theoretical Study of Halogen-Bonded Complexes of DMAP with Di- and Triiodofluorobenzenes. 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A Complex with a Very Short N···I Halogen Bond</atitle><jtitle>Crystal growth & design</jtitle><addtitle>Cryst. Growth Des</addtitle><date>2010-08-04</date><risdate>2010</risdate><volume>10</volume><issue>8</issue><spage>3710</spage><epage>3720</epage><pages>3710-3720</pages><issn>1528-7483</issn><eissn>1528-7505</eissn><abstract>X-ray single crystal structures are reported for 2:1 halogen-bonded complexes of 4-(N,N-dimethylamino)pyridine (DMAP) with 1,4- and 1,3-diiodotetrafluorobenzene and 1,3-diiodo-4,5,6-trifluorobenzene and for a 3:1 complex of DMAP with 1,3,5-triiodotrifluorobenzene. The complex between DMAP and 1,4-diiodotetrafluorobenzene shows the shortest halogen bond recorded for fluorinated iodoarenes. Model systems based on complexes between the same iodofluorobenzenes and ammonia are investigated by Hartree−Fock and DFT calculations to gain insights into the features of halogen bonding in di- and triiodo systems. The calculations reveal a weak charge-transfer component to the halogen bond and account for the lengthening of the C−I bond on complexation in terms of the C−I antibonding character observed within the localized molecular orbital describing the N···I bond.</abstract><cop>Washington,DC</cop><pub>American Chemical Society</pub><doi>10.1021/cg100549u</doi><tpages>11</tpages></addata></record> |
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| subjects | Condensed matter: electronic structure, electrical, magnetic, and optical properties Condensed matter: structure, mechanical and thermal properties Electron states Exact sciences and technology Methods of electronic structure calculations Physics Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Experimental and Theoretical Study of Halogen-Bonded Complexes of DMAP with Di- and Triiodofluorobenzenes. A Complex with a Very Short N···I Halogen Bond |
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