Universität zu Köln

Byrne, Peter A., Kobayashi, Shinjiro, Breugst, Martin ORCID: 0000-0003-0950-8858, Laub, Hans and Mayr, Herbert ORCID: 0000-0003-0768-5199 (2016). Quantification of the nucleophilic reactivity of nicotine. J. Phys. Org. Chem., 29 (12). S. 759 - 768. HOBOKEN: WILEY-BLACKWELL. ISSN 1099-1395

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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). Copyright (c) 2016 John Wiley & Sons, Ltd.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Byrne, Peter A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Kobayashi, Shinjiro UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Laub, Hans UNSPECIFIED UNSPECIFIED UNSPECIFIED Mayr, Herbert UNSPECIFIED orcid.org/0000-0003-0768-5199 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-254568
DOI:	10.1002/poc.3580
Journal or Publication Title:	J. Phys. Org. Chem.
Volume:	29
Number:	12
Page Range:	S. 759 - 768
Date:	2016
Publisher:	WILEY-BLACKWELL
Place of Publication:	HOBOKEN
ISSN:	1099-1395
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language SCALES; CARBOCATIONS; ELECTROPHILICITY Multiple languages Chemistry, Organic; Chemistry, Physical Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/25456