Synthesis, spectroscopy, and theoretical calculations of some 2-thiohydantoin derivatives as possible new fungicides

Synthesis, spectroscopy, and theoretical calculations of some 2-thiohydantoin derivatives as possible new fungicides

We present the synthesis and structure determination for two thiohydantoin compounds (5-benzylidene-2-sulfanylideneimidazolidin-4-one and 5-cinnamylidene-2-sulfanylideneimidazolidin-4-one), proposed as potential novel fungicides. The exact chemical structure of these molecules has not yet been deter...

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Bibliographic Details
Published in:Journal of molecular modeling Vol. 25; no. 9; pp. 268 - 10
Main Authors: Kobyłka, Katarzyna, Żuchowski, Grzegorz, Tejchman, Waldemar, Zborowski, Krzysztof K.
Format: Journal Article
Language:English
Published: Berlin/Heidelberg Springer Berlin Heidelberg 01-09-2019
Springer Nature B.V
Subjects:
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Computer Appl. in Life Sciences
Computer Applications in Chemistry
Density functional theory
Fungicides
Hydantoin
Isomers
Mathematical analysis
Molecular Medicine
Molecular structure
NMR
Nuclear magnetic resonance
Organic chemistry
Original Paper
Pesticides
Spectrum analysis
Synthesis
Theoretical and Computational Chemistry
Zdzislaw Latajka 70th Birthday Festschrift
2-thiohydantoin
Tautomerism
Theoretical calculations
Structure determination
Hydantoin
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Summary:We present the synthesis and structure determination for two thiohydantoin compounds (5-benzylidene-2-sulfanylideneimidazolidin-4-one and 5-cinnamylidene-2-sulfanylideneimidazolidin-4-one), proposed as potential novel fungicides. The exact chemical structure of these molecules has not yet been determined since they can potentially exist in several tautomeric and geometric forms (Z-E isomerism). The geometries of all the theoretically possible structures of the studied compounds were optimised. The calculations were performed at the density functional theory level using the B3LYP functional and the 6-311++G** basis set. Based on our calculations, the most probable structures of the studied compounds were proposed. The theoretical predictions were verified by comparing the calculated IR as well as the 1 H and 13 C NMR spectra with the experimental data. It was documented that both the studied compounds exist predominantly in the tautomeric structure, in which the movable hydrogen is connected to the nitrogen atom in the hydantoin ring. It has been experimentally proven that one of the studied compounds occurs only as a single structure, whereas the other one exists as a mixture of two geometric isomers. Schematic presentation of synthesis reaction and predicted percentage contents of studied compounds in products mixture
ISSN:1610-2940
0948-5023
DOI:10.1007/s00894-019-4146-9