Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds
The ability of the CH group to act as proton donor is now widely accepted, even if the H bonds (HBs), which it forms are typically much weaker than those of the hydroxyl group, particularly for a sp3‐hybridized C. An NH3 nucleophile is allowed to approach both the terminal methyl group and the hydro...
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Wiley-VCH
2025-07-01
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| Online Access: | https://doi.org/10.1002/ceur.202500088 |
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| author | Savannah Rawlings Steve Scheiner |
| author_facet | Savannah Rawlings Steve Scheiner |
| author_sort | Savannah Rawlings |
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| description | The ability of the CH group to act as proton donor is now widely accepted, even if the H bonds (HBs), which it forms are typically much weaker than those of the hydroxyl group, particularly for a sp3‐hybridized C. An NH3 nucleophile is allowed to approach both the terminal methyl group and the hydroxyl of n‐butanol, so as to form either a CH··N or OH··N HB. Density functional theory calculations show that the latter is much stronger than the former. However, the strength of the CH··N HB can be amplified and approach much closer to that of OH··N by appropriate placement of suitable electron‐withdrawing and donating substituents on the butanol. The interaction energy of the CH··N HB reaches above 6–8 kcal mol−1 in several cases, considerably larger than the prototype HB within the water dimer. |
| format | Article |
| id | doaj-art-6778ccc8dfbf45d59067e6da6e94ec21 |
| institution | Kabale University |
| issn | 2751-4765 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Wiley-VCH |
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| series | ChemistryEurope |
| spelling | doaj-art-6778ccc8dfbf45d59067e6da6e94ec212025-08-20T03:30:19ZengWiley-VCHChemistryEurope2751-47652025-07-0134n/an/a10.1002/ceur.202500088Comparison of the CH and OH Groups as Proton Donors within Hydrogen BondsSavannah Rawlings0Steve Scheiner1Department of Chemistry and Biochemistry Utah State University Logan UT 84322‐0300 USADepartment of Chemistry and Biochemistry Utah State University Logan UT 84322‐0300 USAThe ability of the CH group to act as proton donor is now widely accepted, even if the H bonds (HBs), which it forms are typically much weaker than those of the hydroxyl group, particularly for a sp3‐hybridized C. An NH3 nucleophile is allowed to approach both the terminal methyl group and the hydroxyl of n‐butanol, so as to form either a CH··N or OH··N HB. Density functional theory calculations show that the latter is much stronger than the former. However, the strength of the CH··N HB can be amplified and approach much closer to that of OH··N by appropriate placement of suitable electron‐withdrawing and donating substituents on the butanol. The interaction energy of the CH··N HB reaches above 6–8 kcal mol−1 in several cases, considerably larger than the prototype HB within the water dimer.https://doi.org/10.1002/ceur.202500088atoms in moleculesmolecular electrostatic potentialsnuclear magnetic resonance shieldingsredshifts |
| spellingShingle | Savannah Rawlings Steve Scheiner Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds ChemistryEurope atoms in molecules molecular electrostatic potentials nuclear magnetic resonance shieldings redshifts |
| title | Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds |
| title_full | Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds |
| title_fullStr | Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds |
| title_full_unstemmed | Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds |
| title_short | Comparison of the CH and OH Groups as Proton Donors within Hydrogen Bonds |
| title_sort | comparison of the ch and oh groups as proton donors within hydrogen bonds |
| topic | atoms in molecules molecular electrostatic potentials nuclear magnetic resonance shieldings redshifts |
| url | https://doi.org/10.1002/ceur.202500088 |
| work_keys_str_mv | AT savannahrawlings comparisonofthechandohgroupsasprotondonorswithinhydrogenbonds AT stevescheiner comparisonofthechandohgroupsasprotondonorswithinhydrogenbonds |