N‐(Thiocarbamoyl)banzamidine 1 und N‐(Thiocarbamoyl)‐N′‐phenyl‐benzamidine 2 bilden mit Ni2+‐, Pd2+‐, Co3+‐ und Ag+‐Ionen in alkoholischer Lösung kristalline Innerchelatkomplexe1ah und 2ah mit N/S‐Koordination.
Aus ESCA‐Spektren wird im Falle der Chelate von 1 als Haftgruppe NH nachgewiesen und ihre höhere Donorfähigkeit im Vergleich mit dem isosterne Sauerstoffhaftatom gegenüber Nickel fest‐gestellt. Dies wird durch d‐1H‐NMR‐spektroskopisch bestimmte Werte von ΔGc≠ für die behinderte Rotation der Et2N‐Gruppe an 1 a unterstützt.
Reactions of N‐(N′,N′‐Dialkyl(aryl)amino‐thiocarbonyl)benzimidoylchlorides with Potassium Thiocyanate
The treatment of the title compound N‐(amino‐thiocarbonyl)‐benzimidoylchloride 1 with potassium thiocyanate leads in dependence on the solvents (methanol, acetic acid, acetone) either to the 1,3,5‐thiadiazine‐2‐thione 2a–d or to the ring opened isothiocyanate 4a, b. In the case of methanol the N‐(amino‐thiocarbonyl)benzimidates were formed as by‐products.
The structure of the products is confirmed by analytical data and by chemical transformations. 2a reacts with methyl iodide to form the 2‐methylthio‐6‐morpholino‐4‐phenyl‐1,3,5‐thiadiaziniumiodide 3a. From 4a and water the N‐(morpholino‐thiocarbonyl)benzamide 5a arises. The reaction of morpholine with 4a yields the benzamidine 6a.
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