Synthesis of N-Benzoyl-N’-(9,10-Dioxo-9,10-Dihydroanthacen-1-yl) Thioureas and Quantum-Chemical Analysis of the Reaction Passing
Affiliation:
1 Lviv Polytechnic National University
12, S. Bandera str., 79013 Lviv, Ukraine; vnovikov@polynet.lviv.ua
2 Institute of Organic Chemistry of National Academy of Scieces of Ukraine,
5, Murmanska str., 02660 Kyiv, Ukraine
DOI:
https://doi.org/10.23939/chcht08.02.135
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Abstract:
Interaction of an order of aminoanthraquinones with benzoylisothiocyanate resulting in the formation of new N-benzoyl-N’-(9,10-dioxo-9,10-dihydroanthacen-1-yl)-thioureas was investigated. Quantum-chemical calculations using Gaussian 03W and HyperChem 8 were carried out. On their basis nucleophilic addition of aminoanthraquinones to benzoylisothiocyanate (charge control) was confirmed. A probable mechanism of nucleophilic addition was suggested. Influence of ortho-substituents on the passing of the reaction was explained. Values of absolute hardness and softness of aminoanthraquinones were calculated.
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