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

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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, 1H-NMR, 13C-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) Å3, D x = 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 1 = 0.0308 and wR 2 = 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, 1H-NMR, 13C-NMR, UV–visible spectroscopic and X-ray crystallographic techniques.

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Scheme 1
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Scheme 2
Fig. 2

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey

    Mustafa Yıldız & Hava Özay

  2. Department of Physics, Faculty of Science, Ankara University, 06100, Beşevler-Ankara, Turkey

    Hüseyin Ünver, D. Mehmet Zengin & Tahsin Nuri Durlu

  3. Department of Science Education, Ondokuz Mayıs University, 55200, Atakum, Samsun, Turkey

    Nazan Ocak İskeleli

Authors
  1. Mustafa Yıldız
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  2. Hava Özay
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  3. Hüseyin Ünver
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  4. Nazan Ocak İskeleli
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  5. D. Mehmet Zengin
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  6. Tahsin Nuri Durlu
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Correspondence to Hüseyin Ünver.

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Yıldız, M., Özay, H., Ünver, H. et al. Synthesis, Spectroscopic Studies and Structure of 2-[(Benzo[d]thiazol-2-ylamino)methyl]phenol. J Chem Crystallogr 40, 909–913 (2010). https://doi.org/10.1007/s10870-010-9761-3

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