Conformational analysis of natural products

Generalized 3JHH calculation acc. Pachler

3JH,H calculation

The magnitude of three-bond 1H-1H coupling constants is determined mainly by the torsion angle between the protons but substituents, especially electronegative ones, do also affect the coupling. They influence the coupling in two ways; they cause a change in overall magnitude of the Karplus equation, and they cause a shift of the maxima and minima of the curve. Several attempts have been made to account for these effects.

The program here calculates 3JH,H values according to K.G.R. Pachler; J. Chem. Soc., Perkin Trans (1972) 1936-1940 using the electronegativities of Huggins rather than those of Dailey & Shoolery (1955) as the latter is defined for fewer elements and shows some irregularities.
Since the equation requires the relative orientation of the substituents a molecular model will be of help.
Turn the model so that the proton on the near side is pointing up then use the schemes below to determine the numbering of the substituents (e.g. S1, S2 etc.) and select the appropriate elements from the menus.
It is also possible to calculate the torsion angles that correspond to a particular 3JH,H-value. There can be one to four angles depending on the size of the coupling constant.


trans gauche+ gauche-
S1 S2 S3 S4
Enter H,H torsion angle to calculate 3JH,H
Enter 3JH,H value to calculate H,H torsion angle