Empirical Model of Solvophobic Interactions in Organic Solvents
An empirical model was developed to predict organic solvophobic effects using N‐phenylimide molecular balances functionalized with non‐polar alkyl groups. Solution studies and X‐ray crystallography confirmed intramolecular alkyl‐alkyl interactions in their folded conformers. The structural modularit...
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| creator | Manzewitsch, Alexander N. Liu, Hao Lin, Binzhou Li, Ping Pellechia, Perry J. Shimizu, Ken D. |
| description | An empirical model was developed to predict organic solvophobic effects using N‐phenylimide molecular balances functionalized with non‐polar alkyl groups. Solution studies and X‐ray crystallography confirmed intramolecular alkyl‐alkyl interactions in their folded conformers. The structural modularity of the balances allowed systematic variation of alkyl group lengths. Control balances were instrumental in isolating weak organic solvophobic effects by eliminating framework solvent‐solute effects. A 19F NMR label enabled analysis across 46 deuterated and non‐deuterated solvent systems. Linear correlations were observed between organic solvophobic effects and solvent cohesive energy density (ced) as well as changes in solvent‐accessible surface areas (SASA). Using these empirical relationships, a model was constructed to predict organic solvophobic interaction energy per unit area for any organic solvent with known ced values. The predicted interaction energies aligned with recent organic solvophobic measurements and literature values for the hydrophobic effect on non‐polar surfaces confirmed the model‘s accuracy and utility.
An empirical model was developed to predict organic solvophobic effects based on the measurements of a series of N‐phenylimide molecular balances. This model can predict organic solvophobic effects for alkyl‐alkyl interactions or varying lengths in a wide range of solvents. |
| doi_str_mv | 10.1002/anie.202314962 |
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An empirical model was developed to predict organic solvophobic effects based on the measurements of a series of N‐phenylimide molecular balances. This model can predict organic solvophobic effects for alkyl‐alkyl interactions or varying lengths in a wide range of solvents.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202314962</identifier><identifier>PMID: 38032351</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aggregation ; Crystallography ; Deuteration ; Empirical analysis ; Hydrophobic Effect ; Hydrophobicity ; Model accuracy ; Modularity ; Molecular Devices ; NMR ; Nuclear magnetic resonance ; Organic solvents ; Solvent Effects ; Solvents ; Supramolecular Chemistry</subject><ispartof>Angewandte Chemie International Edition, 2024-01, Vol.63 (2), p.e202314962-n/a</ispartof><rights>2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH</rights><rights>2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c4222-e264c886ffd34aa10cbf8800426689a9ba2143253f45e62c9bf84194441a11673</cites><orcidid>0000-0001-9339-3111 ; 0000-0002-0229-6541</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.202314962$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202314962$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38032351$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Manzewitsch, Alexander N.</creatorcontrib><creatorcontrib>Liu, Hao</creatorcontrib><creatorcontrib>Lin, Binzhou</creatorcontrib><creatorcontrib>Li, Ping</creatorcontrib><creatorcontrib>Pellechia, Perry J.</creatorcontrib><creatorcontrib>Shimizu, Ken D.</creatorcontrib><title>Empirical Model of Solvophobic Interactions in Organic Solvents</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An empirical model was developed to predict organic solvophobic effects using N‐phenylimide molecular balances functionalized with non‐polar alkyl groups. Solution studies and X‐ray crystallography confirmed intramolecular alkyl‐alkyl interactions in their folded conformers. The structural modularity of the balances allowed systematic variation of alkyl group lengths. Control balances were instrumental in isolating weak organic solvophobic effects by eliminating framework solvent‐solute effects. A 19F NMR label enabled analysis across 46 deuterated and non‐deuterated solvent systems. Linear correlations were observed between organic solvophobic effects and solvent cohesive energy density (ced) as well as changes in solvent‐accessible surface areas (SASA). Using these empirical relationships, a model was constructed to predict organic solvophobic interaction energy per unit area for any organic solvent with known ced values. The predicted interaction energies aligned with recent organic solvophobic measurements and literature values for the hydrophobic effect on non‐polar surfaces confirmed the model‘s accuracy and utility.
An empirical model was developed to predict organic solvophobic effects based on the measurements of a series of N‐phenylimide molecular balances. This model can predict organic solvophobic effects for alkyl‐alkyl interactions or varying lengths in a wide range of solvents.</description><subject>Aggregation</subject><subject>Crystallography</subject><subject>Deuteration</subject><subject>Empirical analysis</subject><subject>Hydrophobic Effect</subject><subject>Hydrophobicity</subject><subject>Model accuracy</subject><subject>Modularity</subject><subject>Molecular Devices</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic solvents</subject><subject>Solvent Effects</subject><subject>Solvents</subject><subject>Supramolecular Chemistry</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkM9LwzAYhoMobk6vHqXgxUtnfjVNTjLG1MF0B_Uc0izVjLaZSavsvzdzc4IXT_kgz_d8Ly8A5wgOEYT4WjXWDDHEBFHB8AHoowyjlOQ5OYwzJSTNeYZ64CSEZeQ5h-wY9AiHBJMM9cHNpF5Zb7Wqkge3MFXiyuTJVR9u9eYKq5Np0xqvdGtdExLbJHP_Gk_qb8Y0bTgFR6WqgjnbvQPwcjt5Ht-ns_nddDyapZpijFODGdWcs7JcEKoUgrooYxZIMWNcKFEoHMPijJQ0MwxrEb8pEpRSpBBiORmAq6135d17Z0Iraxu0qSrVGNcFibnIcsijM6KXf9Cl63wT00ksYmmECMYiNdxS2rsQvCnlytta-bVEUG6qlZtq5b7auHCx03ZFbRZ7_KfLCIgt8Gkrs_5HJ0eP08mv_AvF3YLK</recordid><startdate>20240108</startdate><enddate>20240108</enddate><creator>Manzewitsch, Alexander N.</creator><creator>Liu, Hao</creator><creator>Lin, Binzhou</creator><creator>Li, Ping</creator><creator>Pellechia, Perry J.</creator><creator>Shimizu, Ken D.</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9339-3111</orcidid><orcidid>https://orcid.org/0000-0002-0229-6541</orcidid></search><sort><creationdate>20240108</creationdate><title>Empirical Model of Solvophobic Interactions in Organic Solvents</title><author>Manzewitsch, Alexander N. ; Liu, Hao ; Lin, Binzhou ; Li, Ping ; Pellechia, Perry J. ; Shimizu, Ken D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4222-e264c886ffd34aa10cbf8800426689a9ba2143253f45e62c9bf84194441a11673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aggregation</topic><topic>Crystallography</topic><topic>Deuteration</topic><topic>Empirical analysis</topic><topic>Hydrophobic Effect</topic><topic>Hydrophobicity</topic><topic>Model accuracy</topic><topic>Modularity</topic><topic>Molecular Devices</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic solvents</topic><topic>Solvent Effects</topic><topic>Solvents</topic><topic>Supramolecular Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Manzewitsch, Alexander N.</creatorcontrib><creatorcontrib>Liu, Hao</creatorcontrib><creatorcontrib>Lin, Binzhou</creatorcontrib><creatorcontrib>Li, Ping</creatorcontrib><creatorcontrib>Pellechia, Perry J.</creatorcontrib><creatorcontrib>Shimizu, Ken D.</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><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>Manzewitsch, Alexander N.</au><au>Liu, Hao</au><au>Lin, Binzhou</au><au>Li, Ping</au><au>Pellechia, Perry J.</au><au>Shimizu, Ken D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Empirical Model of Solvophobic Interactions in Organic Solvents</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2024-01-08</date><risdate>2024</risdate><volume>63</volume><issue>2</issue><spage>e202314962</spage><epage>n/a</epage><pages>e202314962-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An empirical model was developed to predict organic solvophobic effects using N‐phenylimide molecular balances functionalized with non‐polar alkyl groups. Solution studies and X‐ray crystallography confirmed intramolecular alkyl‐alkyl interactions in their folded conformers. The structural modularity of the balances allowed systematic variation of alkyl group lengths. Control balances were instrumental in isolating weak organic solvophobic effects by eliminating framework solvent‐solute effects. A 19F NMR label enabled analysis across 46 deuterated and non‐deuterated solvent systems. Linear correlations were observed between organic solvophobic effects and solvent cohesive energy density (ced) as well as changes in solvent‐accessible surface areas (SASA). Using these empirical relationships, a model was constructed to predict organic solvophobic interaction energy per unit area for any organic solvent with known ced values. The predicted interaction energies aligned with recent organic solvophobic measurements and literature values for the hydrophobic effect on non‐polar surfaces confirmed the model‘s accuracy and utility.
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| subjects | Aggregation Crystallography Deuteration Empirical analysis Hydrophobic Effect Hydrophobicity Model accuracy Modularity Molecular Devices NMR Nuclear magnetic resonance Organic solvents Solvent Effects Solvents Supramolecular Chemistry |
| title | Empirical Model of Solvophobic Interactions in Organic Solvents |
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