Skip to main content
SpringerLink
Log in

Synthesis and Structure Determination of S,S′-(Naphthalen-2-ylmethyl sulfanyl (1-p-tolyl-ethylidene) Hydrazine

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

Abstract

S,S′-(Naphthalen-2-ylmethyl sulfanyl (1-p-tolyl-ethylidene) hydrazine (SNM4MA) was prepared by the condensation of S-napthalen-2-ylmethyldithiocarbazate (SNMDTC) and 4-methylacetophenone. Yellow needles of SNM4MA were obtained upon slow evaporation of a 50:50 mixture of acetonitrile and DMSO over a period of weeks. The compound crystallizes in the monoclinic system with the space group C 2/c and Z = 4. The unit cell parameters are a = 7.0221(2) Å, b = 22.8428(6) Å, c = 23.5127(6) Å with β = 94.0222(13)°. Single crystal X-ray analysis shows that the molecule has crystallographic two-fold rotational symmetry coincident with the S–S bond. The title compound exists as a trans–cis conformer in which the naphthalene group is trans with respect to the thione sulfur while the benzyl group adopts a cis geometry. 13C and 1H spectra confirm that the dimeric nature is retained in DMSO solution.

Graphical Abstract

Single crystal X-ray analysis of S,S′-(naphthalen-2-ylmethyl sulfanyl (1-p-tolyl-ethylidene) hydrazine shows that the molecule is dimeric with a two-fold rotational symmetry coincident with the S–S bond via both the thione sulfur atoms. The molecule was found to retain its dimeric structure in dimethylsulfoxide solution.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Zhou H, Li D, Wang P, Cheng L, Gao Y, Zhu Y, Wu J, Tian Y, Tao Z, Jiang M, Fun HK (2007) J Mol Struc 826(2–3):205–210

    Article  CAS  Google Scholar 

  2. Tian Y, Duan C, You X, Mak TCW, Luo Q, Zhou J (1998) Trans Met Chem 23:17–20

    Article  CAS  Google Scholar 

  3. Boschi A, Bolzati C, Uccelli L, Duatti A (2003) Nucl Med Biol 30:381–387

    Article  CAS  Google Scholar 

  4. Liu G (1997) Nucl Med Biol 24:119–122

    Article  CAS  Google Scholar 

  5. Tarafder MTH, Ali MA, Saravanan N, Weng WY, Kumar S, Umar-Tsafe N, Crouse KA (2000) Trans Met Chem 25:295–298

    Article  CAS  Google Scholar 

  6. Tarafder MTH, Chew KB, Crouse KA, Ali AM, Yamin BM, Fun HK (2002) Polyhedron 21(27–28):2683–2690

    Article  CAS  Google Scholar 

  7. Tarafder MTH, Khoo TJ, Crouse KA, Ali AM, Yamin BM, Fun HK (2002) Polyhedron 21(27–28):2691–2698

    Article  CAS  Google Scholar 

  8. Ali MA, Tarafder MTH (1977) J Inorg Nucl Chem 39:1785–1791

    Article  Google Scholar 

  9. Chan MHE, Crouse KA, Tarafder MTH, Yamin BM (2003) Acta Cryst E59:o628–o629

    CAS  Google Scholar 

  10. How FN-F, Watkin DJ, Crouse KA, Tahir MIM (2007) Acta Cryst E63:o2912

    CAS  Google Scholar 

  11. How FN-F, Watkin DJ, Crouse KA, Tahir MIM (2007) Acta Cryst E63:o3137–o3138

    CAS  Google Scholar 

  12. Otwinowski Z, Minor W (1997) Meth Enzymol 276:307–326

    Article  CAS  Google Scholar 

  13. Altomare A, Cascarano G, Giacovazzo C, Guagliardi A (1994) J Appl Cryst 27:435

    Google Scholar 

  14. Betteridge PW, Carruthers JR, Cooper RI, Prout K, Watkin DJ (2003) J Appl Cryst 36:1487

    Article  CAS  Google Scholar 

  15. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans 2 S1:19

    Google Scholar 

  16. Shan S, Zhan Y-L, Xu D-J (2006) Acta Cryst E62:o1567–o1569

    CAS  Google Scholar 

  17. Ali MA, Mirza AH, Fereday RJ, Butcher RJ, Fuller JM, Drew SC, Gahan LR, Hanson GR, Moubaraki B, Murray KS (2005) Inorg Chim Acta 358(3):3937–3948

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the Ministry of Science, Technology and Innovation (MOSTI), Malaysia, for funding this research under the Intensification of Research in Priority Areas Scheme (IRPA Grant No. 09-02-04-0755-EA001). FHNF thanks MOSTI, for awarding her a National Science Fellowship and supporting her attachment at the Chemical Crystallography Laboratory, Oxford University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Fiona N.-F. How, Karen A. Crouse & M. Ibrahim M. Tahir

  2. Chemical Crystallography Laboratory, Chemical Research Laboratory, University of Oxford, Oxford, OX1 3TA, UK

    David J. Watkin

Authors
  1. Fiona N.-F. How
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Karen A. Crouse
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Ibrahim M. Tahir
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. David J. Watkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Karen A. Crouse.

Rights and permissions

Reprints and permissions

About this article

Cite this article

How, F.NF., Crouse, K.A., Tahir, M.I.M. et al. Synthesis and Structure Determination of S,S′-(Naphthalen-2-ylmethyl sulfanyl (1-p-tolyl-ethylidene) Hydrazine. J Chem Crystallogr 39, 894–897 (2009). https://doi.org/10.1007/s10870-009-9586-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-009-9586-0

Keywords

Search

Navigation