Investigation of Pyramidal Inversion of Nitrogen Atom in Carbamate and Thiocarbamate Ions Formed at the Reaction of СО2, СOS, CS2 with 2-Aminoethanol Full article
Journal |
Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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Output data | Year: 2017, Volume: 53, Number: 11, Pages: 1630-1636 Pages count : 7 DOI: 10.1134/S1070428017110021 | ||
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Abstract:
Dynamic NMR was applied to measuring the value ΔG≠ characterizing the height of the barrier to the pyramidal inversion of the nitrogen atom in carbamate and thiocarbamate anions formed at the reaction of 2-aminoethanol with СО2 and СOS. The refinement was introduced in formerly suggested cyclic structures of anions containing an intramolecular hydrogen bond NH···O(S), which contradicted the found large values of the barrier of inversion (ΔG≠ ~ 70 kJ mol–1). The hydrogen bond in the cyclic anions of carbamates and thiocarbamates is two-electron and three-center. Analogous cyclic structure with a multicenter hydrogen bond does not form in the case of dithiocarbamate anion that is the product of 2-aminoethanol reaction with CS2.
Cite:
Talsi V.P.
, Evdokimov S.N.
Investigation of Pyramidal Inversion of Nitrogen Atom in Carbamate and Thiocarbamate Ions Formed at the Reaction of СО2, СOS, CS2 with 2-Aminoethanol
Russian Journal of Organic Chemistry. 2017. V.53. N11. P.1630-1636. DOI: 10.1134/S1070428017110021 WOS Scopus РИНЦ
Investigation of Pyramidal Inversion of Nitrogen Atom in Carbamate and Thiocarbamate Ions Formed at the Reaction of СО2, СOS, CS2 with 2-Aminoethanol
Russian Journal of Organic Chemistry. 2017. V.53. N11. P.1630-1636. DOI: 10.1134/S1070428017110021 WOS Scopus РИНЦ
Original:
Талзи В.П.
, Евдокимов С.Н.
Исследование пирамидальной инверсии атома азота в карбамат- и тиокарбамат-ионах, образующихся при взаимодействии СО2, СOS, CS2 c 2-аминоэтанолом
Журнал органической химии. 2017. Т.53. №11. С.1598-1604. РИНЦ
Исследование пирамидальной инверсии атома азота в карбамат- и тиокарбамат-ионах, образующихся при взаимодействии СО2, СOS, CS2 c 2-аминоэтанолом
Журнал органической химии. 2017. Т.53. №11. С.1598-1604. РИНЦ
Dates:
Submitted: | Oct 26, 2016 |
Published print: | Nov 1, 2017 |
Published online: | Dec 23, 2017 |
Identifiers:
Web of science | WOS:000418421200002 |
Scopus | 2-s2.0-85039034715 |
Elibrary | 35497898 |
OpenAlex | W2779805467 |