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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.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 | citiraj | |
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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 30.05.2020. 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 30.05.2020.];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 |
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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
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