TY - JOUR
T1 - Conformational preferences for 3-piperideines
T2 - An ab initio and molecular mechanics study
AU - Belostotskii, Anatoly M.
AU - Shokhen, Michael
AU - Gottlieb, Hugo E.
AU - Hassner, Alfred
PY - 2001/11/5
Y1 - 2001/11/5
N2 - Conformational preferences in alkyl- as well as Ph-substituted 3-piperideines (1,2,3,6-tetrahydropyridines) have been characterized by ab initio and molecular mechanics calculations. A set of rules and subrules for estimation of the conformational equilibrium (in terms of preferred substituent orientation) in these systems, with differently positioned ring substituent (-s), is presented. Examples of the revision of some previous stereochemical assignments demonstrate the reliability of these rules.
AB - Conformational preferences in alkyl- as well as Ph-substituted 3-piperideines (1,2,3,6-tetrahydropyridines) have been characterized by ab initio and molecular mechanics calculations. A set of rules and subrules for estimation of the conformational equilibrium (in terms of preferred substituent orientation) in these systems, with differently positioned ring substituent (-s), is presented. Examples of the revision of some previous stereochemical assignments demonstrate the reliability of these rules.
KW - Ab initio calculations
KW - Conformation analysis
KW - NMR spectroscopy
KW - Nitrogen heterocycles
UR - http://www.scopus.com/inward/record.url?scp=0035813698&partnerID=8YFLogxK
U2 - 10.1002/1521-3765(20011105)7:21<4715::AID-CHEM4715>3.0.CO;2-L
DO - 10.1002/1521-3765(20011105)7:21<4715::AID-CHEM4715>3.0.CO;2-L
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C2 - 11757664
SN - 0947-6539
VL - 7
SP - 4715
EP - 4722
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 21
ER -