Long-range electronic interactions in androstanediones

Abstract

The results of MNDO SCF MO calculations on 5␣-androstane 1 , Ž .Ž . Ž . androstan-3-one 2 , androstan-16-one 3 , androstan-17-one 4 , androstane-3,16-dione Ž .Ž .13 5 , and androstane-3,17-dione 6 and the experimental C-NMR chemical shifts observed Ž . in various solvents C D , CDCl , CD CO D, CD Cl , CD COCD , CD OD, CD CN 6 12 3 3 2 2 2 3 3 3 3 were used to assess the nature of long-range interactions between 3,16-and 3,17-carbonyl groups in androstanediones. The 13 C-NMR results appear to confirm the proposition that the interactions in androstane-3,16-dione are stronger.