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Quantification of the nucleophilic reactivity of nicotine
Byrne, Peter A.; Kobayashi, Shinjiro; Breugst, Martin; Laub, Hans; Mayr, Herbert
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).
Keyword(s): Equilibrium constants; Nucleophilicity; Lewis basicity; Kinetics; N‐heterocycles; Scales; Carbocations; Electrophilicity
Publication Date:
Type: Journal article
Peer-Reviewed: Yes
Language(s): English
Institution: University College Cork
Citation(s): 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
Publisher(s): Wiley
File Format(s): application/pdf
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First Indexed: 2019-04-05 06:30:07 Last Updated: 2019-04-05 06:30:07