1JCH correlates with alcohol hydrogen bond strength

J Org Chem. 2006 Mar 31;71(7):2878-80. doi: 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 approximately -0.2 Hz in 1JCH per approximately 1 kJ mol(-1) increase in the H-bond enthalpy. The decrease in 1JCH is attributed to an increased overlap of the H-bonding sigma orbital with the antibonding sigma orbitals of the vicinal C-H bonds.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohols / chemistry*
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards*
  • Models, Chemical
  • Reference Standards
  • Stereoisomerism

Substances

  • Alcohols