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The nicotine analogue 3-(N,N-dimethylaminomethyl)pyridine 2, which reacts with methyl iodide in acetonitrile exclusively on the sp 3 -nitrogen, methylates exclusively on the pyridine nitrogen with trimethyloxonium in the gas phase. Calculations at the RHF/6-31G**//6-31G** level suggest that there is an interaction between the side chain nitrogen and hydrogens on the aromatic ring. This interaction...