Understanding the Formation of 5-(Diethylammoniothio)-1,3-dimethylbarbituric Acid: Crystal Structure and DFT Studies

5-(Diethylammoniothio)-1,3-dimethylbarbituric acid ( 8 ) was obtained in good yield from the reaction of 5-bromo-1,3-dimethylbarbituric acid ( 5 ) and 1,3-diethylthiourea. The obtained product has been characterized using different techniques including single-crystal X-ray diffraction, FTIR, MS and...

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Bibliographic Details
Published in:Journal of chemical crystallography 2021-06, Vol.51 (2), p.215-224
Main Authors: Sweidan, Kamal, Almatarneh, Mansour H., AlDamen, Murad A., Khanfar, Monther, Omeir, Reema A., Mössmer, Caecilia Maichle, Steimann, Manfred
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Crystal structure
Crystallography and Scattering Methods
Crystals
Density functional theory
Inorganic Chemistry
Mathematical models
NMR spectroscopy
Organometallic Chemistry
Original Paper
Physical Chemistry
Single crystals
Solvation
Solvents
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Summary:5-(Diethylammoniothio)-1,3-dimethylbarbituric acid ( 8 ) was obtained in good yield from the reaction of 5-bromo-1,3-dimethylbarbituric acid ( 5 ) and 1,3-diethylthiourea. The obtained product has been characterized using different techniques including single-crystal X-ray diffraction, FTIR, MS and NMR spectroscopy. For this reaction, a detailed computational study of the reaction steps has been performed using density functional theory (DFT). Both thermodynamic and kinetic parameters were calculated. Step B is the most favorable reaction with an activation energy of 33 kJ mol −1 using the solvation model that based on the solvent model density (SMD) calculated at B3LYP/6-31G(d). Graphic abstract The rate-determining step of the most plausible mechanism involves the formation of C-S bond via proton transfer to oxygen (intramolecular attraction) with an activation barrier of 33 kJ mol-1 using the solvation model that based on density (SMD) solvent model calculated at B3LYP/6-31G(d).
ISSN:1074-1542
1572-8854
DOI:10.1007/s10870-020-00846-1