Collect. Czech. Chem. Commun.
2002, 67, 665-678
https://doi.org/10.1135/cccc20020665
9-Isothiocyanatoanthracene as a Versatile Starting Compound in the Chemistry of Anthracen-9-yl Derivatives
Ladislav Janoveca, Gejza Suchára, Ján Imricha, Pavol Kristiana,*, Vlasta Sasinkováb, Juraj Alföldib and Erik Sedlákc
a Department of Organic Chemistry, Faculty of Science, P. J. Šafárik University, SK-04167 Košice, Slovak Republic
b Chemical Institute, Slovak Academy of Sciences, SK-84238 Bratislava, Slovak Republic
c Department of Biochemistry, Faculty of Science, P. J. Šafárik University, SK-04167 Košice, Slovak Republic
Abstract
The synthesis, structure and reactivity of 9-isothiocyanatoanthracene (5) likewise the conformation of the corresponding thioureas (6a-6i) have been studied. The 13C NMR substituent chemical shift values of the NCS group and correlations between spectral parameters (IR, NMR) and rate constans of reactions of 5, acridin-9-yl (14), phenyl (15) and benzoyl isothiocyanate (16) with butylamine were found. Significant increase of the fluorescence of the synthesized anthracenylthioureas with amino acid rests refers to the possibility to use 5 as potential biomarker.
Keywords: Isothiocyanates; Thioureas; 9-Isothiocyanatoanthracene; Anthracenylthioureas; Kinetics; IR spectroscopy; 13C NMR spectroscopy; Fluorescence.
References: 33 live references.
