TY - JOUR
T1 - The 1,3,5,7-tetraazadecalins
T2 - Structure, conformation, and stereoelectronics. Theory vs experiment
AU - Reany, Ofer
AU - Goldberg, Israel
AU - Abramson, Sarah
AU - Golender, Larisa
AU - Ganguly, Bishwajit
AU - Fuchs, Benzion
PY - 1998/11/27
Y1 - 1998/11/27
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0031789009&partnerID=8YFLogxK
U2 - 10.1021/jo9809884
DO - 10.1021/jo9809884
M3 - Article
AN - SCOPUS:0031789009
SN - 0022-3263
VL - 63
SP - 8850
EP - 8859
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -