Collect. Czech. Chem. Commun. 1980, 45, 2400-2409

Dipole moments induced in larger molecules. 1- And 4-substituted diamantanes

Otto Exnera, Václav Jehličkab, Luděk Vodičkac and Pavel Jakoubekc

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Department of Physical Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
c Laboratory of Synthetic Fuels, Prague Institute of Chemical Technology, 166 28 Prague 6


Dipole moments of fourteen monofunctional diamantane derivatives were measured in benzene solution. The values found are almost equal for 1-substituted (IIa-IIg) and 4-subtituted (IIIa to IIIg) isomers but both are distinctly higher than those of the corresponding adamantane derivatives (I). This trend is not accounted for in terms of the classic Smith-Eyring theory of induced moments which works reasonable well for smaller molecules. Probably some basic assumptions of the theory of dielectrics (a spherical molecular cavity with a dipole in its centre) are no more fulfilled for diamantane derivatives.