Aroylthioureas: new organic ionophores for heavy metal ion selective electrodes. A nuclear magnetic resonance study.
The 1H and 13C NMR spectra of four series of 1-aroylthiourea derivatives in DMSO-d6 are reported. The NH signals for 3-alkyl substituted aroylthioureas are identified by their multiplicity and by homonuclear irradiation experiments. Correlation analyzes are made for NH, CO and CS signals in order to determine the best way to modulate the nucleophilic character of the CS group, as thioureas are well-known ionophore groups. Almost all 1,3-substituted thioureas (Series 2-4) show the reported chelated structure with the exception of those with CF3, CN and NO2 groups. Pyridine group promote a different equilibrium in solution. The fragment -CO-NH- transmits poorly the electronic effects of substituents in the aroylgroup.
Otazo-Sánchez
E
E
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, Colonia Ciudad Universitaria, Pachuca, Mexico. elenaotazo@yahoo.com
Ortiz-del-Toro
P
P
Estévez-Hernández
O
O
Pérez-Marín
L
L
Goicoechea
I
I
Beltran
A Cerón
AC
Villagómez-Ibarra
J R
JR
D004566:Electrodes; D007476:Ionophores / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D019216:Metals, Heavy; D008958:Models, Molecular; D015394:Molecular Structure; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry*
D007476:Ionophores; D019216:Metals, Heavy; D013890:Thiourea