Quantification of the nucleophilic reactivity of nicotine

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dc.contributor.author Byrne, Peter A.
dc.contributor.author Kobayashi, Shinjiro
dc.contributor.author Breugst, Martin
dc.contributor.author Laub, Hans
dc.contributor.author Mayr, Herbert
dc.date.accessioned 2019-04-04T11:40:57Z
dc.date.available 2019-04-04T11:40:57Z
dc.date.issued 2016-05-31
dc.identifier.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 en
dc.identifier.volume 29 en
dc.identifier.startpage 759 en
dc.identifier.endpage 767 en
dc.identifier.issn 0894-3230
dc.identifier.uri http://hdl.handle.net/10468/7710
dc.identifier.doi 10.1002/poc.3580 en
dc.description.abstract 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). en
dc.description.sponsorship Deutsche 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.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Wiley en
dc.relation.uri https://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.subject Equilibrium constants en
dc.subject Nucleophilicity en
dc.subject Lewis basicity en
dc.subject Kinetics en
dc.subject N‐heterocycles en
dc.subject Scales en
dc.subject Carbocations en
dc.subject Electrophilicity en
dc.title Quantification of the nucleophilic reactivity of nicotine en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Peter Byrne, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: peter.byrne@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2019-03-26T17:48:51Z
dc.description.version Accepted Version en
dc.internal.rssid 383418235
dc.internal.wokid WOS:000387884300011
dc.contributor.funder Deutsche Forschungsgemeinschaft en
dc.contributor.funder Verband der Chemischen Industrie en
dc.contributor.funder Alexander von Humboldt-Stiftung en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Journal of Physical Organic Chemistry en
dc.internal.copyrightchecked No
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress peter.byrne@ucc.ie en


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