Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents
While research into deep eutectic solvents (DESs) has expanded over the previous two decades, the focus has remained on the utilization of hydrogen bond donors in these systems. Additionally, the majority of the known DESs rely on at least one ionic component. Through the combination of 1,3‐dithiane...
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| creator | Peloquin, Andrew J. McCollum, Jena M. McMillen, Colin D. Pennington, William T. |
| description | While research into deep eutectic solvents (DESs) has expanded over the previous two decades, the focus has remained on the utilization of hydrogen bond donors in these systems. Additionally, the majority of the known DESs rely on at least one ionic component. Through the combination of 1,3‐dithiane and 1,2‐diiodo‐3,4,5,6‐tetrafluorobenzene (1,2‐F4DIB), we report the first known DES based on halogen bonding. This mixture remains a liquid, with a eutectic melting temperature of 13.7 °C over a range of 1,3‐dithiane mole fraction (0.35 to 0.75). Additionally, cocrystals of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction. These data reveal a wide range of halogen bonding strengths (0.85 |
| doi_str_mv | 10.1002/anie.202110520 |
| format | Article |
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By combining 1,3‐dithiane and 1,2‐diiodotetrafluorobenzene (1,2‐F4DIB), the first halogen bonding‐based deep eutectic solvent is reported. This mixture remains a liquid, with a eutectic point of 13.7 °C, over a wide compositional range. The other combinations of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202110520</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bonding strength ; chalcogen bonding ; crystal engineering ; deep eutectic solvent ; Eutectic temperature ; halogen bonding ; Hydrogen bonding ; Hydrogen bonds ; Hydrophobicity ; Melt temperature ; Solvents ; Sulfur ; X-ray diffraction</subject><ispartof>Angewandte Chemie International Edition, 2021-10, Vol.60 (42), p.22983-22989</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3500-2869031acb9c5ae4f34ebd8d398ce9defd3ae83780150c05854dd7fad0f992f23</citedby><cites>FETCH-LOGICAL-c3500-2869031acb9c5ae4f34ebd8d398ce9defd3ae83780150c05854dd7fad0f992f23</cites><orcidid>0000-0002-7773-8797 ; 0000-0002-7535-2049 ; 0000-0002-7532-9121 ; 0000-0001-5224-7046</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%2Fanie.202110520$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202110520$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Peloquin, Andrew J.</creatorcontrib><creatorcontrib>McCollum, Jena M.</creatorcontrib><creatorcontrib>McMillen, Colin D.</creatorcontrib><creatorcontrib>Pennington, William T.</creatorcontrib><title>Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents</title><title>Angewandte Chemie International Edition</title><description>While research into deep eutectic solvents (DESs) has expanded over the previous two decades, the focus has remained on the utilization of hydrogen bond donors in these systems. Additionally, the majority of the known DESs rely on at least one ionic component. Through the combination of 1,3‐dithiane and 1,2‐diiodo‐3,4,5,6‐tetrafluorobenzene (1,2‐F4DIB), we report the first known DES based on halogen bonding. This mixture remains a liquid, with a eutectic melting temperature of 13.7 °C over a range of 1,3‐dithiane mole fraction (0.35 to 0.75). Additionally, cocrystals of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction. These data reveal a wide range of halogen bonding strengths (0.85<RXB<0.99; RXB=normalized halogen bond distance parameter) and geometries about the sulfur atom. By including intermolecular interactions beyond hydrogen bonding, the scope of possible DES systems can be greatly expanded.
By combining 1,3‐dithiane and 1,2‐diiodotetrafluorobenzene (1,2‐F4DIB), the first halogen bonding‐based deep eutectic solvent is reported. This mixture remains a liquid, with a eutectic point of 13.7 °C, over a wide compositional range. The other combinations of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction.</description><subject>Bonding strength</subject><subject>chalcogen bonding</subject><subject>crystal engineering</subject><subject>deep eutectic solvent</subject><subject>Eutectic temperature</subject><subject>halogen bonding</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Hydrophobicity</subject><subject>Melt temperature</subject><subject>Solvents</subject><subject>Sulfur</subject><subject>X-ray diffraction</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EElBYmS2xsKT4I24ctlIKrcTHAMyRa5_BKNjFToDy6zEqAomF6e6k5z3dPQgdUDKkhLBj5R0MGWGUEsHIBtqhgtGCVxXfzH3JeVFJQbfRbkpPmZeSjHaQm6k2PIDHp8Eb5x-w8_jMdY9OeTieBxNs24cYFuA_wAO-cu9dHyGd4DG-hjc8aVVKOFg8W5kYlo9h4TQ-A1jiad-B7vJ0G9pX8F3aQ1tWtQn2v-sA3Z9P7yaz4vLmYj4ZXxaaC0IKJkc14VTpRa2FgtLyEhZGGl5LDbUBa7gCyStJqCCaCClKYyqrDLF1zSzjA3S03ruM4aWH1DXPLmlo2_xR6FPDxIiXjAlRZ_TwD_oU-ujzdZmqZMUZy_YGaLimdAwpRbDNMrpnFVcNJc2X-ebLfPNjPgfqdeDNtbD6h27G1_Ppb_YTDjmHsw</recordid><startdate>20211011</startdate><enddate>20211011</enddate><creator>Peloquin, Andrew J.</creator><creator>McCollum, Jena M.</creator><creator>McMillen, Colin D.</creator><creator>Pennington, William T.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7773-8797</orcidid><orcidid>https://orcid.org/0000-0002-7535-2049</orcidid><orcidid>https://orcid.org/0000-0002-7532-9121</orcidid><orcidid>https://orcid.org/0000-0001-5224-7046</orcidid></search><sort><creationdate>20211011</creationdate><title>Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents</title><author>Peloquin, Andrew J. ; McCollum, Jena M. ; McMillen, Colin D. ; Pennington, William T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3500-2869031acb9c5ae4f34ebd8d398ce9defd3ae83780150c05854dd7fad0f992f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Bonding strength</topic><topic>chalcogen bonding</topic><topic>crystal engineering</topic><topic>deep eutectic solvent</topic><topic>Eutectic temperature</topic><topic>halogen bonding</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Hydrophobicity</topic><topic>Melt temperature</topic><topic>Solvents</topic><topic>Sulfur</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peloquin, Andrew J.</creatorcontrib><creatorcontrib>McCollum, Jena M.</creatorcontrib><creatorcontrib>McMillen, Colin D.</creatorcontrib><creatorcontrib>Pennington, William T.</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peloquin, Andrew J.</au><au>McCollum, Jena M.</au><au>McMillen, Colin D.</au><au>Pennington, William T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2021-10-11</date><risdate>2021</risdate><volume>60</volume><issue>42</issue><spage>22983</spage><epage>22989</epage><pages>22983-22989</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>While research into deep eutectic solvents (DESs) has expanded over the previous two decades, the focus has remained on the utilization of hydrogen bond donors in these systems. Additionally, the majority of the known DESs rely on at least one ionic component. Through the combination of 1,3‐dithiane and 1,2‐diiodo‐3,4,5,6‐tetrafluorobenzene (1,2‐F4DIB), we report the first known DES based on halogen bonding. This mixture remains a liquid, with a eutectic melting temperature of 13.7 °C over a range of 1,3‐dithiane mole fraction (0.35 to 0.75). Additionally, cocrystals of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction. These data reveal a wide range of halogen bonding strengths (0.85<RXB<0.99; RXB=normalized halogen bond distance parameter) and geometries about the sulfur atom. By including intermolecular interactions beyond hydrogen bonding, the scope of possible DES systems can be greatly expanded.
By combining 1,3‐dithiane and 1,2‐diiodotetrafluorobenzene (1,2‐F4DIB), the first halogen bonding‐based deep eutectic solvent is reported. This mixture remains a liquid, with a eutectic point of 13.7 °C, over a wide compositional range. The other combinations of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.202110520</doi><tpages>7</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-7773-8797</orcidid><orcidid>https://orcid.org/0000-0002-7535-2049</orcidid><orcidid>https://orcid.org/0000-0002-7532-9121</orcidid><orcidid>https://orcid.org/0000-0001-5224-7046</orcidid></addata></record> |
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| subjects | Bonding strength chalcogen bonding crystal engineering deep eutectic solvent Eutectic temperature halogen bonding Hydrogen bonding Hydrogen bonds Hydrophobicity Melt temperature Solvents Sulfur X-ray diffraction |
| title | Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents |
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