1JCH Correlates with Alcohol Hydrogen Bond Strength
- 2 March 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (7) , 2878-2880
- https://doi.org/10.1021/jo052389k
Abstract
The strength of the H-bond donation by alcohols is reflected in the carbon−hydrogen bond of the H−C−O−H functional group. The one-bond 13C−1H spin−spin coupling constant of hexafluoroisopropanol (HFIP) correlates with the strength of the H-bond in various HFIP−amine complexes with a slope of ∼ −0.2 Hz in 1JCH per ∼1 kJ mol-1 increase in the H-bond enthalpy. The decrease in 1JCH is attributed to an increased overlap of the H-bonding σ orbital with the antibonding σ* orbitals of the vicinal C−H bonds.Keywords
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