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Croatica Chemica Acta, Vol. 87 No. 4, 2014.

Izvorni znanstveni članak
https://doi.org/10.5562/cca2447

Proton Affinities of Organocatalysts Derived from Pyridine N-oxide

Jiří Váňa ; Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic
Jana Roithová   ORCID icon orcid.org/0000-0001-5144-0688 ; Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic
Martin Kotora ; Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic
Pavel Beran ; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic
Lubomír Rulíšek ; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic
Pavel Kočovský ; Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 12843 Prague 2, Czech Republic;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic

Puni tekst: engleski, pdf (3 MB) str. 349-356 preuzimanja: 931* citiraj
APA 6th Edition
Váňa, J., Roithová, J., Kotora, M., Beran, P., Rulíšek, L. i Kočovský, P. (2014). Proton Affinities of Organocatalysts Derived from Pyridine N-oxide. Croatica Chemica Acta, 87 (4), 349-356. https://doi.org/10.5562/cca2447
MLA 8th Edition
Váňa, Jiří, et al. "Proton Affinities of Organocatalysts Derived from Pyridine N-oxide." Croatica Chemica Acta, vol. 87, br. 4, 2014, str. 349-356. https://doi.org/10.5562/cca2447. Citirano 09.05.2021.
Chicago 17th Edition
Váňa, Jiří, Jana Roithová, Martin Kotora, Pavel Beran, Lubomír Rulíšek i Pavel Kočovský. "Proton Affinities of Organocatalysts Derived from Pyridine N-oxide." Croatica Chemica Acta 87, br. 4 (2014): 349-356. https://doi.org/10.5562/cca2447
Harvard
Váňa, J., et al. (2014). 'Proton Affinities of Organocatalysts Derived from Pyridine N-oxide', Croatica Chemica Acta, 87(4), str. 349-356. https://doi.org/10.5562/cca2447
Vancouver
Váňa J, Roithová J, Kotora M, Beran P, Rulíšek L, Kočovský P. Proton Affinities of Organocatalysts Derived from Pyridine N-oxide. Croatica Chemica Acta [Internet]. 2014 [pristupljeno 09.05.2021.];87(4):349-356. https://doi.org/10.5562/cca2447
IEEE
J. Váňa, J. Roithová, M. Kotora, P. Beran, L. Rulíšek i P. Kočovský, "Proton Affinities of Organocatalysts Derived from Pyridine N-oxide", Croatica Chemica Acta, vol.87, br. 4, str. 349-356, 2014. [Online]. https://doi.org/10.5562/cca2447

Sažetak
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 de-termined 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 proper¬ties of 2,2′-bipyridyl N,N′-dioxides. Last but not least, the theoretically predicted pKa 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.

Ključne riječi
density functional theory; isodesmic reactions; kinetic method; mass spectrometry; organocatalysis; proton affinity; superbases

Hrčak ID: 131528

URI
https://hrcak.srce.hr/131528

Posjeta: 1.227 *