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Structural study of 3‐methyl‐3‐azabicyclo[3.3.1]nonan‐9‐ols functionalized at the 1‐position by molecular mechanics calculations and NMR spectroscopy
Author(s) -
AriasPérez M. S.,
Alejo A.,
Maroto A.,
Pérez S. M.
Publication year - 2000
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/1099-1395(200011)13:11<699::aid-poc303>3.0.co;2-c
Subject(s) - chemistry , hydroxymethyl , molecular mechanics , nonane , bicyclic molecule , stereochemistry , nuclear magnetic resonance spectroscopy , epimer , diol , cyclohexane conformation , spectroscopy , conformational isomerism , computational chemistry , molecular dynamics , hydrogen bond , molecule , organic chemistry , physics , quantum mechanics
The α and β epimers of 1‐hydroxymethyl‐3‐methyl‐3‐azabicyclo[3.3.1]nonan‐9‐ol ( 1 and 2 ) and ethyl 9‐hydroxy‐3‐methyl‐3‐azabicyclo[3.3.1]nonane‐1‐carboxylate ( 3 and 4 ) were studied by molecular mechanics and 1 H and 13 C NMR spectroscopy. These compounds always prefer a slightly flattened chair–chair (CC) conformation with the N ‐CH 3 group in the equatorial position. It can be assumed that the bicyclic system exists as a single conformation except for diol 2 in non‐polar solvents, where the contribution of the N…H—O bonded BC form is estimated to be around 39%. Theoretical calculations provide reasonably good support for the observed conformational preferences of the hydroxymethyl and ethoxycarbonyl groups. Copyright © 2000 John Wiley & Sons, Ltd.