Skip to main content
SpringerLink
Log in

Formation of 3,5-Dithio-cyclopentenyl Ligand on Fe2(CO)6 Support from Photochemical Reaction of Internal Acetylenes with [Fe(CO)5] in Presence of CS2

  • Original Paper
  • Published:
Journal of Cluster Science Aims and scope Submit manuscript

Abstract

Photolytic reaction of internal acetylenes, RC≡CR’ (R = Ph, Fc and R’ = C≡CPh, C≡CFc, CHO) with iron pentacarbonyl, in presence of CS2, in hexane yields a 3,5-dithiacyclopentene ligand system supported on a Fe2(CO)6 framework. On reaction with diacetylenes substituted cis- and trans-3,5-dithiacyclopentene ligand, formed by the coupling of two molecules of the diacetylenes are observed, while, with 3-ferrocenylpropynal, along with coupled 3-ferrocenylpropynal products, cis-3,5-dithiacyclopentene ligand, formed by the coupling of one 3-ferrocenylpropynal and one ferrocenylacetylene is also observed. All compounds have been characterized by IR, 1H NMR and 13C NMR spectroscopy, mass spectrometry, and structures of 4a and 4c have been established by single crystal X-ray diffraction technique. In addition, DFT computational analyses of compounds 4a and 4c have been investigated in order to understand the bonding in complexes 4a and 4c.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. A. J. Deeming (1986). Adv. Organomet. Chem. 26, 1.

    CAS  Google Scholar 

  2. H. Bönnermann (1985). Angew. Chem. 24, 248.

    Article  Google Scholar 

  3. P. Mathur, M. O. Ahmed, J. H. Kaldis, and M. J. McGlinchey (2002). Dalton Trans. 619.

  4. P. Mathur, M. O. Ahmed, A. K. Dash, M. G. Walawalkar, and V. G. Puranik (2000). Dalton. Trans. 2916.

  5. P. Mathur, S. Mukhopadhyay, G. K. Lahiri, S. Chakravorty, and C. Thöne (2002). Organometallics 21, 5209.

    Article  CAS  Google Scholar 

  6. D. F. Shriver, H. D. Kaesz and R. D. Adams (eds.) The Chemistry of Metal Cluster Complexes (Wiley, New York, 1990).

    Google Scholar 

  7. P. Braunstein, L. A. Oro and P. R. Raithby (eds.) Metal Cluster in Chemistry, vol. 1–3 (Wiley, Weinheim, 1999).

    Google Scholar 

  8. P. Mathur (1997). Adv. Organomet. Chem. 41, 243.

    CAS  Google Scholar 

  9. T. J. Katz, S. M. Hacker, R. D. Kendrick, and C. S. Yannoni (1985). J. Am. Chem. Soc. 107, 2182.

    Article  CAS  Google Scholar 

  10. P. Mathur, B. Manimaran, R. Trivedi, C. V. V. Satyanarayana, and R. K. Chadha (1998). J. Clust. Sci. 9, 45.

    Article  CAS  Google Scholar 

  11. P. Mathur, S. Ghosh, A. Sarkar, C. V. V. Satyanarayana, and V. G. Puranik (1997). Organometallics 16, 4392.

    Article  CAS  Google Scholar 

  12. P. Mathur, S. Boodida, R. S. Ji, and S. M. Mobin (2009). J. Organomet. Chem. 694, 3043.

    Article  CAS  Google Scholar 

  13. P. Mathur, A. K. Singh, V. K. Singh, P. Singh, R. Rahul, S. M. Mobin, and C. Thöne (2005). Organometallics 24, 4793.

    Article  CAS  Google Scholar 

  14. P. Mathur, V. K. Singh, A. K. Singh, S. M. Mobin, and C. Thöne (2006). J. Organomet. Chem. 691, 3336.

    Article  CAS  Google Scholar 

  15. P. Mathur, A. K. Singh, J. R. Mohanty, S. Chatterjee, and S. M. Mobin (2008). Organometallics 27, 5094.

    Article  CAS  Google Scholar 

  16. P. Mathur, A. K. Bhunia, S. M. Mobin, V. K. Singh, and Ch Srinivasu (2004). Organometallics 23, 3694.

    Article  CAS  Google Scholar 

  17. P. Mathur, V. K. Singh, S. M. Mobin, C. Srinivasu, R. Trivedi, A. K. Bhunia, and V. G. Puranik (2005). Organometallics 24, 367.

    Article  CAS  Google Scholar 

  18. P. Mathur, D. K. Rai, M. Tauqeer, S. M. Mobin, and G. K. Lahiri (2012). J. Organomet. Chem. 721–722, 144.

    Article  Google Scholar 

  19. P. Mathur, R. S. Ji, M. Tauqeer, S. M. Mobin, and G. K. Lahiri (2012). J. Organomet. Chem. 721–722, 186.

    Article  Google Scholar 

  20. P. Mathur, V. D. Avasare, and S. M. Mobin (2009). J. Clust. Sci. 20, 399.

    Article  CAS  Google Scholar 

  21. P. Mathur, A. Das, S. Chatterjee, and S. M. Mobin (2008). J. Organomet. Chem. 693, 1919.

    Article  CAS  Google Scholar 

  22. P. Mathur, R. S. Ji, S. Boodida, A. K. Singh, and S. M. Mobin (2010). J. Organomet. Chem. 695, 1919.

    Google Scholar 

  23. M. I. Bruce, B. W. Skelton, A. H. White, and N. N. Zaitseva (2002). J. Organomet. Chem. 650, 188.

    Article  CAS  Google Scholar 

  24. M. I. Bruce, N. N. Zaitseva, B. W. Skelton, and A. H. White (1996). Inorg. Chim Acta. 250, 129.

    Article  CAS  Google Scholar 

  25. R. D. Adams, B. Qu, M. D. Smith, and T. A. Albright (2002). Organometallics 21, 2970.

    Article  CAS  Google Scholar 

  26. M. I. Bruce, N. N. Zaitseva, B. W. Skelton, and A. H. White (1997). J. Organomet. Chem. 536–537, 93.

    Article  Google Scholar 

  27. M. I. Bruce, B. W. Skelton, A. H. White, and N. N. Zaitseva (1998). Inorg. Chem. Commun. 1, 134.

    Article  CAS  Google Scholar 

  28. P. Mathur, R. S. Ji, D. K. Rai, A. Raghuvanshi, and S. M. Mobin (2012). J. Organomet. Chem. 695, 1919.

    Google Scholar 

  29. T. Fassler, D. Buchholz, G. Huttner, and L. Zsolnai (1989). J. Organomet. Chem. 369, 297.

    Article  CAS  Google Scholar 

  30. P. Mathur, A. K. Dash, M. M. Hossain, S. B. Umbarkar, C. V. V. Satyanarayana, Y.-S. Chen, E. M. Holt, S. N. Rao, and M. Soriano (1996). Organometallics 15, 1356.

    Article  CAS  Google Scholar 

  31. P. Mathur and M. M. Hossain (1993). Organometallics 12, 2398.

    Article  CAS  Google Scholar 

  32. P. Mathur, M. M. Hossain, S. N. Datta, R.-K. Kondru, and M. M. Bhadbhade (1994). Organometallics 13, 2532.

    Article  CAS  Google Scholar 

  33. A. R. Luxmoore and M. R. Truter (1962). Acta Crystallogr. 15, 1117.

    Article  CAS  Google Scholar 

  34. F. A. Cotton and P. Lahuerta (1975). Inorg. Chem. 14, 116.

    Article  CAS  Google Scholar 

  35. M. A. Bennett, G. B. Robertson, I. B. Tomkins, and P. O. Whimp (1972). J. Chem. Soc. Chem. Commun. 341.

  36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, GAUSSIAN 09 (Revision A.1), (Gaussian, Inc., Wallingford, 2009).

  37. S. Grimme (2006). Comput. Chem. 27, 1787.

    Article  CAS  Google Scholar 

  38. A. Ansari, and G. Rajaraman, Phys. Chem. Chem. Phys. doi:10.1039/C3CP55430A.

  39. A. Ansari, A. Kaushik, and G. Rajaraman (2013). J. Am. Chem. Soc 135, 4235.

    Article  CAS  Google Scholar 

  40. A. Bassan, M. R. A. Blomberg, P. E. M. Siegbahn, and L. Que Jr (2005). Angew. Chem. Int. Ed. 44, 2939.

    Article  CAS  Google Scholar 

  41. P. E. M. Siegbahn (2006). J. Biol. Inorg. Chem. 11, 695.

    Article  CAS  Google Scholar 

  42. H. J. Dunning, and P. J. Hay, in H. F Schaefer III (ed.), Modern Theoretical Chemistry, (Plenum, New York, 1976) Vol. 3, pp. 1.

  43. P. J. Hay and W. R. Wadt (1985). J. Chem. Phys. 82, 270.

    Article  CAS  Google Scholar 

  44. P. J. Hay and W. R. Wadt (1985). J. Chem. Phys. 82, 299.

    Article  CAS  Google Scholar 

  45. W. R. Wadt and P. J. Hay (1985). J. Chem. Phys. 82, 284.

    Article  CAS  Google Scholar 

  46. R. Ditchfield, W. J. Hehre, and J. A. Pople (1971). J. Chem. Phys. 54, 724.

    Article  CAS  Google Scholar 

  47. G. M. Sheldrick (2008). Acta Crystallogr. A64, 112.

    Article  Google Scholar 

Download references

Acknowledgments

P.M. is grateful to the Department of Science and Technology, Government of India for support. M.T., R.S.J and D.K.R are grateful to Union Grant Commission (UGC) and Council of Scientific and Industrial Research (CSIR), Government of India for research fellowships. We gratefully acknowledge G. Rajaraman, S. K. Singh., M. Ansari and especially A. Ansari of the fruitful discussion for DFT study.

Author information

Authors and Affiliations

  1. School of Basic Sciences, Indian Institute of Technology Indore, Khandwa Road, Indore, 452017, India

    Pradeep Mathur & Shaikh M. Mobin

  2. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India

    Pradeep Mathur, Mohd. Tauqeer, Radhe Shyam Ji, Dhirendra K. Rai & Goutam K. Lahiri

  3. Sophisticated Instrument Center, Indian Institute of Technology Indore, Khandwa Road, Indore, 452017, India

    Pradeep Mathur & Shaikh M. Mobin

Authors
  1. Pradeep Mathur
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohd. Tauqeer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Radhe Shyam Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dhirendra K. Rai
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shaikh M. Mobin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Goutam K. Lahiri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Pradeep Mathur.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mathur, P., Tauqeer, M., Ji, R.S. et al. Formation of 3,5-Dithio-cyclopentenyl Ligand on Fe2(CO)6 Support from Photochemical Reaction of Internal Acetylenes with [Fe(CO)5] in Presence of CS2 . J Clust Sci 26, 157–167 (2015). https://doi.org/10.1007/s10876-014-0727-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10876-014-0727-z

Keywords

Search

Navigation