LONG-RANGE ELECTRONIC INTERACTIONS IN ANDROSTANEDIONES

The results of MNDO SCF MO calculations on 5 alpha-androstane (1), and rostan-3-one (2), androstan-16-one (3), androstan-17-one (4), androsta ne-3,16-dione (5), and androstane-3,17-dione (6) and the experimental C-13-NMR chemical shifts observed in various solvents (C6D12, CDCl3, C D3CO2D, CD2Cl2, CD3COCD3, CD3OD, CD3CN) were used to assess the nature of long-range interactions between 3,16- and 3,17-carbonyl groups in androstanediones. The C-13-NMR results appear to confirm the propositi on that the interactions in androstane-3,16-dione are stronger. (C) 19 97 John Wiley & Sons, Inc.