Citation:Byrne, P. A., Kobayashi, S., Breugst, M., Laub, H. and Mayr, H. (2016) 'Quantification of the nucleophilic reactivity of nicotine', Journal of Physical Organic Chemistry, 29(12), pp. 759-767. doi: 10.1002/poc.3580
Rate and equilibrium constants of the reactions of nicotine and structurally related compounds with benzhydrylium ions have been determined UV-Vis spectroscopically using stopped-flow and laser-flash techniques. The pyridine nitrogen of nicotine was identified as the site of thermodynamically and kinetically controlled attack. Quantum chemical calculations showed that the introduction of a pyrid-3-yl moiety into the 2-position of N-methylpyrrolidine (to give nicotine) reduces the Lewis basicity of the pyrrolidine ring by 24kJmol(-1), whereas the analogous introduction of a phenyl ring decreases this quantity by only 11kJmol(-1).
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