Structural Chemistry

, Volume 3, Issue 5, pp 301–305 | Cite as

Electron distribution on an intramolecular hydrogen bond: A semiempirical AM1 study

  • Peter Ertl
  • Otto Exner


Dipole moments of seven molecules were studied by AM1, each containing an intramolecular hydrogen bond between a hydroxyl group and a carbonyl or nitro group as hydrogen acceptors. The hydrogen bond causes two electron shifts: from H to O within the hydroxyl group and from C to O within the carbonyl group. The latter is accompanied by withdrawal of electrons from even more distant atoms. If the total electron density change is expressed as a vector, its direction is close to the direction of the O-H bond. This electron redistribution is in agreement with the previous, somewhat, puzzling experimental results. However, it differs from the commonly accepted picture according to which electron density changes on the hydrogen acceptor moiety are less important than those on the O-H bond.


Hydrogen Physical Chemistry Hydroxyl Hydrogen Bond Carbonyl 
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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • Peter Ertl
    • 1
  • Otto Exner
    • 2
  1. 1.Department of ChemistryComenius UniversityBratislavaCzechoslovakia
  2. 2.Institute of Organic Chemistry and BiochemistryCzechoslovak Academy of SciencesPrague 6Czechoslovakia

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