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volume 22 issue 2 pages 111-116

Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid

Publication typeJournal Article
Publication date2016-03-26
scimago Q3
wos Q3
SJR0.292
CiteScore3.4
Impact factor1.5
ISSN07930283, 21910197
Organic Chemistry
Abstract

This article deals with spectrophotometric and ab initio studies of 1,3-diethyl-7-hydroxy-5,5,7-trimethyl-2-thioxo-1,2,3,5,6,7-hexahydro-4Hpyrano[2,3-d]pyrimidin-4-one (HDEAC). Acid-base properties for I = 0.25 and in a strongly acidic solution of HCl (I → 0) were investigated. The obtained value of pKa (5.79±0.02) and -pKH (1.68±0.03) show that this compound is a weaker acid than thiobarbituric acid. For interpretation of the spectrophotometric data the ab initio methods with density functional theory at level PBE0/cc-pVDZ/SMD were used. The most energetically favorable structures for neutral and cationic forms of HDEAC were proposed.

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GOST Copy
Lutoshkin M. A., Golovnev N. N. Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid // Heterocyclic Communications. 2016. Vol. 22. No. 2. pp. 111-116.
GOST all authors (up to 50) Copy
Lutoshkin M. A., Golovnev N. N. Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid // Heterocyclic Communications. 2016. Vol. 22. No. 2. pp. 111-116.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1515/hc-2016-0011
UR - https://doi.org/10.1515/hc-2016-0011
TI - Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid
T2 - Heterocyclic Communications
AU - Lutoshkin, Maxim Alexandrovich
AU - Golovnev, Nicolay Nicolaevich
PY - 2016
DA - 2016/03/26
PB - Walter de Gruyter
SP - 111-116
IS - 2
VL - 22
SN - 0793-0283
SN - 2191-0197
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Lutoshkin,
author = {Maxim Alexandrovich Lutoshkin and Nicolay Nicolaevich Golovnev},
title = {Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid},
journal = {Heterocyclic Communications},
year = {2016},
volume = {22},
publisher = {Walter de Gruyter},
month = {mar},
url = {https://doi.org/10.1515/hc-2016-0011},
number = {2},
pages = {111--116},
doi = {10.1515/hc-2016-0011}
}
MLA
Cite this
MLA Copy
Lutoshkin, Maxim Alexandrovich, and Nicolay Nicolaevich Golovnev. “Acid-base properties and keto-enol equilibrium of a 5-substituted derivative of 1,3-diethyl-2-thiobarbituric acid.” Heterocyclic Communications, vol. 22, no. 2, Mar. 2016, pp. 111-116. https://doi.org/10.1515/hc-2016-0011.