Abstract
AbstractThe 17O NMR chemical shifts of 14 N‐methylpiperidine‐N‐oxides and five N‐methyltetradecahydroacridine‐N‐oxides were measured. The effects of steric factors, such as γ‐gauche and 1,3‐syn‐axial interactions of the N+—O− oxygen, on the 17O chemical shifts are discussed, and evidence for the main contribution of electrostatic interactions, rather than true steric compression, to the so‐called ‘steric effects’ on 17O chemical shifts of alcohols, ethers, sulfoxides and amine oxides is presented. For conformationally mobile compounds, the discussion of the chemical shifts is assisted by results from molecular mechanics (MM+) calculations. Copyright © 2001 John Wiley & Sons, Ltd.
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