Peer-Reviewed Journal Details
Mandatory Fields
Byrne, PA;Kobayashi, S;Breugst, M;Laub, H;Mayr, H
2016
December
Journal Of Physical Organic Chemistry
Quantification of the nucleophilic reactivity of nicotine
Validated
()
Optional Fields
SCALES CARBOCATIONS ELECTROPHILICITY
29
759
767
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). Copyright (c) 2016 John Wiley & Sons, Ltd.
HOBOKEN
0894-3230
10.1002/poc.3580
Grant Details