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Proton Affinities of Organocatalysts Derived from Pyridine N-oxide
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SYSNO ASEP 0441769 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Proton Affinities of Organocatalysts Derived from Pyridine N-oxide Author(s) Váňa, J. (CZ)
Roithová, J. (CZ)
Kotora, Martin (UOCHB-X) RID, ORCID
Beran, Pavel (UOCHB-X)
Rulíšek, Lubomír (UOCHB-X) RID, ORCID
Kočovský, Pavel (UOCHB-X) ORCID, RIDNumber of authors 6 Source Title Croatica Chemica Acta. - : Croatian Chemical Society - ISSN 0011-1643
Roč. 87, č. 4 (2014), s. 349-356Number of pages 8 s. Language eng - English Country HR - Croatia Keywords density functional theory ; isodesmic reactions ; kinetic method ; mass spectrometry ; organocatalysis ; proton affinity ; superbases Subject RIV CF - Physical ; Theoretical Chemistry R&D Projects GA14-31419S GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 UT WOS 000348414100011 EID SCOPUS 84920126715 DOI 10.5562/cca2447 Annotation Proton affinities of several efficient organocatalysts METHOX, QUINOX, ANETOX, KOTOX, FUREOX, and FUROOX bearing a pyridine N-oxide or 2,2'-bipyridyl N,N'-dioxide. moiety were determined by using extended kinetic method and density functional theory calculations. Proton affinities are in the range of 1030-1060 kJ mol(-1). Using isodesmic reactions, the effect of combining two pyridine N-oxide units in the neutral and the protonated molecule was studied: The combination of an unfavorable interaction in the former case and a favorable interaction in the latter accounts for the superbasic properties of 2,2'-bipyridyl N,N'-dioxides. Last but not least, the theoretically predicted pK(a) in ethanol are 0.1, -2.7, 0.9, 1.8, 1.9, and 2.3 for the METHOX, QUINOX, ANETOX, FUROOX, FUREOX, and KOTOX, respectively. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2015
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