The “Nitrogen Effect”: Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents
Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. This is even more challenging for three‐component ternary assemblies of pure organic compounds. In this work, we overcome these...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2023-03, Vol.18 (6), p.e202201308-n/a |
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| creator | Twum, Kwaku Nadimi, Sanaz Osei, Frank Boateng Puttreddy, Rakesh Ojong, Yvonne Bessem Hayward, John J. Rissanen, Kari Trant, John F. Beyeh, Ngong Kodiah |
| description | Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. This is even more challenging for three‐component ternary assemblies of pure organic compounds. In this work, we overcome these complications by leveraging the binding of fused aromatic N‐heterocycles in an open resorcinarene cavity to template the formation of a three‐component halogen‐bonded ternary assembly in a protic polar solvent system.
Fused aromatic N‐heterocycle quinoline templates a halogen‐bonded ternary assembly with resorcinarene and 1‐iodonoonafluorobutane in a highly competitive solvent environment, while phenanthroline templates a dimeric capsule in pure methanol. |
| doi_str_mv | 10.1002/asia.202201308 |
| format | Article |
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Fused aromatic N‐heterocycle quinoline templates a halogen‐bonded ternary assembly with resorcinarene and 1‐iodonoonafluorobutane in a highly competitive solvent environment, while phenanthroline templates a dimeric capsule in pure methanol.</description><subject>Bonding strength</subject><subject>Chemistry</subject><subject>Dimeric capsules</subject><subject>Halogen bond</subject><subject>Intermolecular forces</subject><subject>N-Heterocycles</subject><subject>Organic compounds</subject><subject>Resorcinarenes</subject><subject>Solvents</subject><subject>Ternary assemblies</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkbtOwzAUhi0E4lJYGZElFpYWX9LYYStVS5HKRQIktsh1TsAoiUvsAN1YeAt4OZ4EQ6FILEznl87nT7Z_hLYp6VBC2L5yRnUYYYxQTuQSWqcypu1I0OvlRWZyDW04d0dIl5FErqI1HgvSjaRYRy-Xt4Dfn19Pja_tDVR4kOeg_fvz2wHu23JawJPyxlb40fhbfKJ0bfVMF-DwufVQeaN8yMPGQYZH4GGx9hYPbV3ikSq-vIe2yhw21ZcVvPHmAfCFLR6CxG2ilVwVDra-ZwtdDQeX_VF7fHZ03O-N25ozKdvxRCZdxhJgXEGmALgQijMaEc1zPpE8PJVQGUmZcDXhWuckS3QW0UjSjJKYt9De3Dut7X0DzqelcRqKQlVgG5cyIQilCY9oQHf_oHe2qatwu0DJWMRdwZJAdeZU-BfnasjTaW1KVc9SStLPgtLPgtJFQeHAzre2mZSQLfCfRgKQzIFHU8DsH13auzju_co_ALVRnzA</recordid><startdate>20230314</startdate><enddate>20230314</enddate><creator>Twum, Kwaku</creator><creator>Nadimi, Sanaz</creator><creator>Osei, Frank Boateng</creator><creator>Puttreddy, Rakesh</creator><creator>Ojong, Yvonne Bessem</creator><creator>Hayward, John J.</creator><creator>Rissanen, Kari</creator><creator>Trant, John F.</creator><creator>Beyeh, Ngong Kodiah</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5390-0609</orcidid><orcidid>https://orcid.org/0000-0002-4780-4968</orcidid><orcidid>https://orcid.org/0000-0002-6028-6480</orcidid><orcidid>https://orcid.org/0000-0002-1208-5051</orcidid><orcidid>https://orcid.org/0000-0002-2221-526X</orcidid><orcidid>https://orcid.org/0000-0002-7282-8419</orcidid><orcidid>https://orcid.org/0000-0003-0223-7602</orcidid><orcidid>https://orcid.org/0000-0002-7502-7780</orcidid><orcidid>https://orcid.org/0000-0003-3935-1812</orcidid></search><sort><creationdate>20230314</creationdate><title>The “Nitrogen Effect”: Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents</title><author>Twum, Kwaku ; Nadimi, Sanaz ; Osei, Frank Boateng ; Puttreddy, Rakesh ; Ojong, Yvonne Bessem ; Hayward, John J. ; Rissanen, Kari ; Trant, John F. ; Beyeh, Ngong Kodiah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3288-6b895229e23aedaee377a32140c3f3b8372801848893ab3ccf0d9cd41481d1063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Bonding strength</topic><topic>Chemistry</topic><topic>Dimeric capsules</topic><topic>Halogen bond</topic><topic>Intermolecular forces</topic><topic>N-Heterocycles</topic><topic>Organic compounds</topic><topic>Resorcinarenes</topic><topic>Solvents</topic><topic>Ternary assemblies</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Twum, Kwaku</creatorcontrib><creatorcontrib>Nadimi, Sanaz</creatorcontrib><creatorcontrib>Osei, Frank Boateng</creatorcontrib><creatorcontrib>Puttreddy, Rakesh</creatorcontrib><creatorcontrib>Ojong, Yvonne Bessem</creatorcontrib><creatorcontrib>Hayward, John J.</creatorcontrib><creatorcontrib>Rissanen, Kari</creatorcontrib><creatorcontrib>Trant, John F.</creatorcontrib><creatorcontrib>Beyeh, Ngong Kodiah</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Twum, Kwaku</au><au>Nadimi, Sanaz</au><au>Osei, Frank Boateng</au><au>Puttreddy, Rakesh</au><au>Ojong, Yvonne Bessem</au><au>Hayward, John J.</au><au>Rissanen, Kari</au><au>Trant, John F.</au><au>Beyeh, Ngong Kodiah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The “Nitrogen Effect”: Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem Asian J</addtitle><date>2023-03-14</date><risdate>2023</risdate><volume>18</volume><issue>6</issue><spage>e202201308</spage><epage>n/a</epage><pages>e202201308-n/a</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Bonding strength Chemistry Dimeric capsules Halogen bond Intermolecular forces N-Heterocycles Organic compounds Resorcinarenes Solvents Ternary assemblies |
| title | The “Nitrogen Effect”: Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents |
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