Quantifying the ability of the CF2H group as a hydrogen bond donor
The CF2H group can act as a hydrogen bond donor, serving as a potential surrogate for OH or SH groups but with a weaker hydrogen bond donation ability. Here, we describe a series of CF2H group-containing moieties that facilitate hydrogen bond interactions. We survey hydrogen bond donation ability us...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.11 |
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| author | Matthew E. Paolella Daniel S. Honeycutt Bradley M. Lipka Jacob M. Goldberg Fang Wang |
| author_facet | Matthew E. Paolella Daniel S. Honeycutt Bradley M. Lipka Jacob M. Goldberg Fang Wang |
| author_sort | Matthew E. Paolella |
| collection | DOAJ |
| description | The CF2H group can act as a hydrogen bond donor, serving as a potential surrogate for OH or SH groups but with a weaker hydrogen bond donation ability. Here, we describe a series of CF2H group-containing moieties that facilitate hydrogen bond interactions. We survey hydrogen bond donation ability using several established methods, including 1H NMR-based hydrogen bond acidity determination, UV–vis spectroscopy titration with Reichardt's dye, and 1H NMR titration using tri-n-butylphosphine oxide as a hydrogen bond acceptor. Our experiments reveal that the direct attachment of the CF2H group to cationic aromatic systems significantly enhances its hydrogen bond donation ability, a result consistent with theoretical calculations. We anticipate that this chemistry will be valuable for designing functional molecules for chemical biology and medicinal chemistry applications. |
| format | Article |
| id | doaj-art-22ffda80f23749feb5eb99cc81ed52b3 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-22ffda80f23749feb5eb99cc81ed52b32025-02-03T09:10:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-01-0121118919910.3762/bjoc.21.111860-5397-21-11Quantifying the ability of the CF2H group as a hydrogen bond donorMatthew E. Paolella0Daniel S. Honeycutt1Bradley M. Lipka2Jacob M. Goldberg3Fang Wang4Department of Chemistry, University of Rhode Island, 140 Flagg Rd, Kingston, RI 02881, USA Department of Chemistry, University of Rhode Island, 140 Flagg Rd, Kingston, RI 02881, USA Department of Chemistry, University of Rhode Island, 140 Flagg Rd, Kingston, RI 02881, USA Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, NY 13346, USA Department of Chemistry, University of Rhode Island, 140 Flagg Rd, Kingston, RI 02881, USA The CF2H group can act as a hydrogen bond donor, serving as a potential surrogate for OH or SH groups but with a weaker hydrogen bond donation ability. Here, we describe a series of CF2H group-containing moieties that facilitate hydrogen bond interactions. We survey hydrogen bond donation ability using several established methods, including 1H NMR-based hydrogen bond acidity determination, UV–vis spectroscopy titration with Reichardt's dye, and 1H NMR titration using tri-n-butylphosphine oxide as a hydrogen bond acceptor. Our experiments reveal that the direct attachment of the CF2H group to cationic aromatic systems significantly enhances its hydrogen bond donation ability, a result consistent with theoretical calculations. We anticipate that this chemistry will be valuable for designing functional molecules for chemical biology and medicinal chemistry applications.https://doi.org/10.3762/bjoc.21.11bioisosteredifluoromethyl (cf2h)fluorinehydrogen bond donorshydrogen bond strength |
| spellingShingle | Matthew E. Paolella Daniel S. Honeycutt Bradley M. Lipka Jacob M. Goldberg Fang Wang Quantifying the ability of the CF2H group as a hydrogen bond donor Beilstein Journal of Organic Chemistry bioisostere difluoromethyl (cf2h) fluorine hydrogen bond donors hydrogen bond strength |
| title | Quantifying the ability of the CF2H group as a hydrogen bond donor |
| title_full | Quantifying the ability of the CF2H group as a hydrogen bond donor |
| title_fullStr | Quantifying the ability of the CF2H group as a hydrogen bond donor |
| title_full_unstemmed | Quantifying the ability of the CF2H group as a hydrogen bond donor |
| title_short | Quantifying the ability of the CF2H group as a hydrogen bond donor |
| title_sort | quantifying the ability of the cf2h group as a hydrogen bond donor |
| topic | bioisostere difluoromethyl (cf2h) fluorine hydrogen bond donors hydrogen bond strength |
| url | https://doi.org/10.3762/bjoc.21.11 |
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