Skip to main content
Log in

Structural and Spectral Analyses of 2-[(2-Benzothiazolylmethyl)thio]-benzenamine and 2-[(2-Benzothiazolylmethyl)thio]-benzenamine hydrobromide

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

2-[2-benzothiazoylmethyl)thio]-benzenamine, which was first reported in 1898, was isolated from the reaction of bromoacetyl bromide and 2-aminothiophenol [1]. 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.

Graphical Abstract

The structural, NMR, and mass spectral analyses of 2-[(2-benzothiazolylmethyl)thio]-benzenamine and 2-[(2-benzothiazolylmethyl)thio]-benzenamine hydrobromide salt are presented.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Unger O, Graff G (1898) Chem Ber 30:2389

    Google Scholar 

  2. Cymerman-Craig J, Rogers WP, Warwick GP (1995) Aust J Chem 8:252

    Article  Google Scholar 

  3. Jurisson SS, Lydon JD (1999) Chem Rev 99:2205

    Article  CAS  Google Scholar 

  4. Jones AG, Davison A, LaTegola MR, Brodack JW, Orvig C, Sohn M, Toothaker AK, Lock CJL, Franklin KJ, Costello CE, Carr SA, Biemann K, Kaplan ML (1982) J Nucl Med 23:801

    CAS  Google Scholar 

  5. Heeg MJ, Jurisson SS (1998) Acc Chem Res 32:1053

    Article  Google Scholar 

  6. Fritzberg AR, Kuni CC, Klingensmith WC III, Stevens J, Whitney WP (1982) J Nucl Med 23:592

    CAS  Google Scholar 

  7. Oya S, Plsössl K, Kung M-P, Stevenson DA, Kung HF (1998) Nucl Med Biol 25:135

    Article  CAS  Google Scholar 

  8. Sheldrick GM (2008) Acta Cryst A64:112

    CAS  Google Scholar 

  9. Barbour LJ (2001) J Supramol Chem 1:189

    Article  CAS  Google Scholar 

  10. Mike JF, Inteman JJ, Ellern A, Jeffries-EL M (2010) J Org Chem 75:495

    Article  CAS  Google Scholar 

  11. Jiang X-J (2010) Acta Cryst E66:1075

    Google Scholar 

  12. Chen Y, Zheng Y-Y, Wu G, Wang M, Chen H-Z, Yang H (2010) Acta Cryst E66:417

    Google Scholar 

Download references

Acknowledgments

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).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Silvia S. Jurisson.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Demoin, D.W., Barnes, C.L., Hoffman, T.J. et al. Structural and Spectral Analyses of 2-[(2-Benzothiazolylmethyl)thio]-benzenamine and 2-[(2-Benzothiazolylmethyl)thio]-benzenamine hydrobromide. J Chem Crystallogr 42, 508–512 (2012). https://doi.org/10.1007/s10870-011-9996-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-9996-7

Keywords

Navigation