caa a22 4500 605529612 CHVBK 20210128100819.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1134/S1070428015030045 doi (NATIONALLICENCE)springer-10.1134/S1070428015030045 Quantum chemical study of mechanisms of organic reactions: IV. Nucleophilic addition of ethylene glycol to 4-hydroxybut-2-ynenitrile [Elektronische Daten] [E. Chirkina, A. Mal'kina, L. Krivdin] A theoretical mechanism has been proposed for nucleophilic addition of ethylene glycol to 4-hydroxybut-2-ynenitrile on the basis of DFT quantum chemical calculations at the B3LYP/6-311++G(d,p) level of theory. The reaction catalyzed by alkali involves nucleophilic attack by 2-hydroxyethoxide ion on the β-carbon atom of the acetylenic alcohol with intermediate formation of vinylic carbanion which undergoes intramolecular cyclization with closure of 1,3-dioxolane ring. Pleiades Publishing, Ltd., 2015 Chirkina E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Mal'kina A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Krivdin L. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 313-318 1070-4280 51:3<313 2015 51 11178 https://doi.org/10.1134/S1070428015030045 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015030045 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chirkina E. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Mal'kina A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Krivdin L. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 313-318 1070-4280 51:3<313 2015 51 11178