%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 (7−9) and N-acyl (10−12)
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