Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites
The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picoli...
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Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2021-08, Vol.86 (8), p.1049-1057 |
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description | The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picolinamides (2Pyr‐X), N‐(pyridin‐2‐yl)nicotinamides (3Pyr‐X), N‐(pyridin‐2‐yl)isonicotinamides (4Pyr‐X); X=H/Cl/Br/I. The structural outcomes were compared with interactions in the targets themselves. 13 co‐crystals were analysed by single‐crystal X‐ray diffraction (SCXRD). In all three co‐crystals from the 2Pyr series, the intramolecular HB remained intact while the XB donors engaged with the N(pyr) or O=C sites. In the ten co‐crystals from the other three series, the intermolecular HBs present in the individual targets were disrupted in 9/10 cases. Overall, the acceptor sites selected by the halogen‐bond donors in these targets were distributed as follows; N(pyr)=81 %, O=C (15 %) or π (4 %).
A series of co‐crystallization experiments with halogen bond donors and sixteen target molecules was carried out to map preferred binding sites of halogen‐bond donors, and it was found to be in the order of π (4 %) |
doi_str_mv | 10.1002/cplu.202100102 |
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A series of co‐crystallization experiments with halogen bond donors and sixteen target molecules was carried out to map preferred binding sites of halogen‐bond donors, and it was found to be in the order of π (4 %)<O=C(15 %)<N(pyr)=81 %.</description><identifier>ISSN: 2192-6506</identifier><identifier>EISSN: 2192-6506</identifier><identifier>DOI: 10.1002/cplu.202100102</identifier><identifier>PMID: 34008343</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Benzamide ; Chemical bonds ; Chemistry ; co-crystals ; crystal engineering ; Crystals ; halogen bonding ; hydrogen bonding ; Hydrogen bonds ; supramolecular chemistry</subject><ispartof>ChemPlusChem (Weinheim, Germany), 2021-08, Vol.86 (8), p.1049-1057</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3732-43ac0f2759f71c716ceae69c97cac7aac863b05d129153272f711e2c7c5a20713</citedby><cites>FETCH-LOGICAL-c3732-43ac0f2759f71c716ceae69c97cac7aac863b05d129153272f711e2c7c5a20713</cites><orcidid>0000-0002-8947-2068</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcplu.202100102$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcplu.202100102$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34008343$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abeysekera, Amila M.</creatorcontrib><creatorcontrib>Averkiev, Boris B.</creatorcontrib><creatorcontrib>Sinha, Abhijeet S.</creatorcontrib><creatorcontrib>Le Magueres, Pierre</creatorcontrib><creatorcontrib>Aakeröy, Christer B.</creatorcontrib><title>Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites</title><title>ChemPlusChem (Weinheim, Germany)</title><addtitle>Chempluschem</addtitle><description>The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picolinamides (2Pyr‐X), N‐(pyridin‐2‐yl)nicotinamides (3Pyr‐X), N‐(pyridin‐2‐yl)isonicotinamides (4Pyr‐X); X=H/Cl/Br/I. The structural outcomes were compared with interactions in the targets themselves. 13 co‐crystals were analysed by single‐crystal X‐ray diffraction (SCXRD). In all three co‐crystals from the 2Pyr series, the intramolecular HB remained intact while the XB donors engaged with the N(pyr) or O=C sites. In the ten co‐crystals from the other three series, the intermolecular HBs present in the individual targets were disrupted in 9/10 cases. Overall, the acceptor sites selected by the halogen‐bond donors in these targets were distributed as follows; N(pyr)=81 %, O=C (15 %) or π (4 %).
A series of co‐crystallization experiments with halogen bond donors and sixteen target molecules was carried out to map preferred binding sites of halogen‐bond donors, and it was found to be in the order of π (4 %)<O=C(15 %)<N(pyr)=81 %.</description><subject>Benzamide</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>co-crystals</subject><subject>crystal engineering</subject><subject>Crystals</subject><subject>halogen bonding</subject><subject>hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>supramolecular chemistry</subject><issn>2192-6506</issn><issn>2192-6506</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqF0LtOwzAUBmALgQAVVkYUiYWl5fg4iZsRKm5SK0DAHLmnp62Rm4Q4EWLjEXhGngRXLRex4MU-0udf9i_EgYSeBMATqlzbQ8AwSMANsYsyw26aQLr567wj9r1_grBSSFCrbbGjYoC-itWuuDv3jRk76-e2mEVXxpUzLj7e3s_KYhLd1jzlmgtiH9kiGpWOqXVheLHNPBq1rrGV4-iUiKumrKN727DfE1tT4zzvr_eOeLw4fxhcdYc3l9eD02GXlFbYjZUhmKJOsqmWpGVKbDjNKNNkSBtD_VSNIZlIzGSiUGNgkpE0JQZBS9URx6vcqi6fW_ZNvrCe2DlTcNn6HBPsZ6ghxUCP_tCnsq2L8Lqg0iTTALEKqrdSVJfeh6_nVW0Xpn7NJeTLvvNl3_l33-HC4Tq2HS948s2_2g0gW4EX6_j1n7h8cDt8_An_BHhNi7k</recordid><startdate>202108</startdate><enddate>202108</enddate><creator>Abeysekera, Amila M.</creator><creator>Averkiev, Boris B.</creator><creator>Sinha, Abhijeet S.</creator><creator>Le Magueres, Pierre</creator><creator>Aakeröy, Christer B.</creator><general>Blackwell Publishing Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>4T-</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8947-2068</orcidid></search><sort><creationdate>202108</creationdate><title>Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites</title><author>Abeysekera, Amila M. ; Averkiev, Boris B. ; Sinha, Abhijeet S. ; Le Magueres, Pierre ; Aakeröy, Christer B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3732-43ac0f2759f71c716ceae69c97cac7aac863b05d129153272f711e2c7c5a20713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Benzamide</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>co-crystals</topic><topic>crystal engineering</topic><topic>Crystals</topic><topic>halogen bonding</topic><topic>hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>supramolecular chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abeysekera, Amila M.</creatorcontrib><creatorcontrib>Averkiev, Boris B.</creatorcontrib><creatorcontrib>Sinha, Abhijeet S.</creatorcontrib><creatorcontrib>Le Magueres, Pierre</creatorcontrib><creatorcontrib>Aakeröy, Christer B.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Docstoc</collection><collection>MEDLINE - Academic</collection><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abeysekera, Amila M.</au><au>Averkiev, Boris B.</au><au>Sinha, Abhijeet S.</au><au>Le Magueres, Pierre</au><au>Aakeröy, Christer B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites</atitle><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle><addtitle>Chempluschem</addtitle><date>2021-08</date><risdate>2021</risdate><volume>86</volume><issue>8</issue><spage>1049</spage><epage>1057</epage><pages>1049-1057</pages><issn>2192-6506</issn><eissn>2192-6506</eissn><abstract>The interplay between hydrogen bonds (HBs) and halogen bonds (XBs), has been addressed by co‐crystallizing two halogen bond donors, 1,4‐diiodotetrafluorbenzene(DITFB) and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene(TITFB) with four series of targets; N‐(pyridin‐2‐yl)benzamide (Bz‐X), N‐(pyridin‐2‐yl)picolinamides (2Pyr‐X), N‐(pyridin‐2‐yl)nicotinamides (3Pyr‐X), N‐(pyridin‐2‐yl)isonicotinamides (4Pyr‐X); X=H/Cl/Br/I. The structural outcomes were compared with interactions in the targets themselves. 13 co‐crystals were analysed by single‐crystal X‐ray diffraction (SCXRD). In all three co‐crystals from the 2Pyr series, the intramolecular HB remained intact while the XB donors engaged with the N(pyr) or O=C sites. In the ten co‐crystals from the other three series, the intermolecular HBs present in the individual targets were disrupted in 9/10 cases. Overall, the acceptor sites selected by the halogen‐bond donors in these targets were distributed as follows; N(pyr)=81 %, O=C (15 %) or π (4 %).
A series of co‐crystallization experiments with halogen bond donors and sixteen target molecules was carried out to map preferred binding sites of halogen‐bond donors, and it was found to be in the order of π (4 %)<O=C(15 %)<N(pyr)=81 %.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>34008343</pmid><doi>10.1002/cplu.202100102</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-8947-2068</orcidid></addata></record> |
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subjects | Benzamide Chemical bonds Chemistry co-crystals crystal engineering Crystals halogen bonding hydrogen bonding Hydrogen bonds supramolecular chemistry |
title | Establishing Halogen‐Bond Preferences in Molecules with Multiple Acceptor Sites |
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