%0 Journal Article %A Reany, Ofer %A Goldberg, Israel %A Abramson, Sarah %A Golender, Larisa %A Ganguly, Bishwajit %A Fuchs, Benzion %D 1998 %T The 1,3,5,7-Tetraazadecalins:  Structure, Conformation, and Stereoelectronics. Theory vs Experiment1 %U https://acs.figshare.com/articles/journal_contribution/The_1_3_5_7-Tetraazadecalins_Structure_Conformation_and_Stereoelectronics_Theory_vs_Experiment_sup_1_sup_/3714447 %R 10.1021/jo9809884.s001 %2 https://ndownloader.figshare.com/files/5805903 %K stereoelectronic effects %K TAD %K anomeric effect %K trans series %K MM 3 force fields %K ab initio %K theory vs Experiment 1 cis %K QM %X cis- and trans-1,3,5,7-tetraazadecalin (TAD) (2 and 4) and several N-Me (79) and N-acyl (1012) substituted derivatives in the cis and trans series were prepared and characterized. The X-ray structures of 4 and 12 were analyzed and the conformational equilibria of 2 and 11 were evaluated by VT-NMR. A QM (ab initio) and MM computational study was carried out, to provide relative stabilities and geometrical parameters, which were compared with experiment. The MM2-AE (modified for the anomeric effect in N−C−N containing molecules) and MM3 force fields are useful tools for these systems. The results were interpreted in the light of stereoelectronic effects in such fused 1,3-diazane systems. %I ACS Publications