Structural and Spectral Analyses of 2-[(2-Benzothiazolylmethyl)thio]-benzenamine and 2-[(2-Benzothiazolylmethyl)thio]-benzenamine hydrobromide
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2-[2-benzothiazoylmethyl)thio]-benzenamine, which was first reported in 1898, was isolated from the reaction of bromoacetyl bromide and 2-aminothiophenol . The product crystallized from an aqueous methanol solution of the reaction mixture to which nickel(II) acetate had been added. 2-[(2-benzothiazolylmethyl)thio]-benzenamine crystallized in the monoclinic system, in space group C2/c, with cell dimensions of a = 27.392 (19) Å, b = 4.730 (3) Å, and c = 23.686 (16) Å, β = 122.465 (6)°, V = 2589(3) Å3, Z = 8 and refined to R = 0.0343 and R w = 0.0844. Crystallization from methanol yielded the product as the hydrobromide salt in the monoclinic space group Cc, with cell dimensions of a = 10.488 (3) Å, b = 33.404 (9) Å, c = 5.2578 (14) Å, β = 116.769(2)°, V = 1644.7(8) Å3, Z = 4 and refined to R = 0.0296 and R w = 0.0600. Mass spectral and NMR analyses confirmed that the bulk and crystalline compound were all 2-[(2-benzothiazolylmethyl)thio]-benzenamine.
Keywords2-[(2-Benzothiazolylmethyl)thio]-benzenamine 2-[(2-Benzothiazolylmethyl)thio]-benzenamine hydrobromide Crystal structure Mass spectrum 2-(2′-Aminophenylthio)methylbenzthiazole Nuclear magnetic resonance
The authors acknowledge the University of Missouri Mass Spectroscopy Facility; National Science Foundation grant NSF-CHE-89-08304 for the use of the NMR facility, and NSF-CHE-9011804 for the use of the X-ray facility; Dr. Wei Wycoff for assistance with the 500 MHz NMR; and NIBIB Training Grant NIBIB 5 T32 EB004822 (D.W.D.). The crystallographic data has been deposited with the Cambridge Crystallographic Data Centre (CCDC).
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