Synthesis, Spectroscopic Studies and Structure of 2-[(Benzo[ d ]thiazol-2-ylamino)methyl]phenol

Abstract

Schiff base (E)-2-[(benzo[d]thiazol-2-ylimino)methyl]phenol (1) has been synthesized from the reaction of 2-hydroxy-benzaldehyde with 2-aminobenzothiazole. The 2-[(benzo[d]thiazol-2-ylamino)methyl]phenol (2) was prepared reduction of the Schiff base 1 with sodium borohydride. The compounds 1 and 2 have been characterized by elemental analysis, FT-IR, 1 H-NMR, 13 C-NMR and UV-visible spectroscopic techniques. The structure of the compound 2 has also been examined crystallographically. The compound 2 crystallizes in the monoclinic space group P2/c. The unit cell parameters were found as a = 10.017(1), b = 11.725(1), c = 10.341(1) Å, V = 1208.1(1) Å 3 , D <inf>x</inf> = 1.409 g cm -3 and Z = 4. The crystal structure was solved by direct methods and refined by the full-matrix least squares method and found as R <inf>1</inf> = 0.0308 and wR <inf>2</inf> = 0.0818 for 2032 for the observed reflections [I > 2σ(I)]. Graphical Abstract: Crystal and molecular structure of the compound 2-[(benzo[d]thiazol-2- ylamino)methyl]phenol have been studied in order to reveal the presence of either the enol-imine or keto-amine forms related with hydrogen bonding by using FT-IR, 1 H-NMR, 13 C-NMR, UV-visible spectroscopic and X-ray crystallographic techniques.[Figure not available: see fulltext.] © 2010 Springer Science+Business Media, LLC.