Quantification of the nucleophilic reactivity of nicotine

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dc.contributor.authorByrne, Peter A.
dc.contributor.authorKobayashi, Shinjiro
dc.contributor.authorBreugst, Martin
dc.contributor.authorLaub, Hans
dc.contributor.authorMayr, Herbert
dc.contributor.funderDeutsche Forschungsgemeinschaften
dc.contributor.funderVerband der Chemischen Industrieen
dc.contributor.funderAlexander von Humboldt-Stiftungen
dc.date.accessioned2019-04-04T11:40:57Z
dc.date.available2019-04-04T11:40:57Z
dc.date.issued2016-05-31
dc.date.updated2019-03-26T17:48:51Z
dc.description.abstractRate 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).en
dc.description.sponsorshipDeutsche Forschungsgemeinschaft (SFB 749, Project B1); Verband der Chemischen Industrie (Fonds der Chemischen Industrie (Liebig-scholarship)); Alexander von Humboldt-Stiftung (Humboldt Foundation Research Fellowship)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationByrne, 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.3580en
dc.identifier.doi10.1002/poc.3580en
dc.identifier.endpage767en
dc.identifier.issn0894-3230
dc.identifier.journaltitleJournal of Physical Organic Chemistryen
dc.identifier.startpage759en
dc.identifier.urihttps://hdl.handle.net/10468/7710
dc.identifier.volume29en
dc.language.isoenen
dc.publisherWileyen
dc.relation.urihttps://onlinelibrary.wiley.com/doi/full/10.1002/poc.3580
dc.rights© 2016 John Wiley & Sons, Ltd. This is the peer reviewed version of the following article: Byrne, P. A., Kobayashi, S., Breugst, M., Laub, H., and Mayr, H. (2016) Quantification of the nucleophilic reactivity of nicotine. J. Phys. Org. Chem., 29: 759-767, which has been published in final form at https://doi.org/10.1002/poc.3580. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.en
dc.subjectEquilibrium constantsen
dc.subjectNucleophilicityen
dc.subjectLewis basicityen
dc.subjectKineticsen
dc.subjectN‐heterocyclesen
dc.subjectScalesen
dc.subjectCarbocationsen
dc.subjectElectrophilicityen
dc.titleQuantification of the nucleophilic reactivity of nicotineen
dc.typeArticle (peer-reviewed)en
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