Skip to main content
SpringerLink
Log in

4,5-, 3,6-, and 3,4,5,6-tert-Butylsulfanylphthalonitriles: synthesis and comparative structural and spectroscopic analyses

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Three tert-butylsulfanylphthalonitriles have been prepared with optimized synthetic procedures. Their comparative structural analyses have been completed, with a focus on IR and NMR spectroscopy and refined X-ray structural data. Miscellaneous parameters such as UV absorption, melting points, and related polarity of the compounds are summarized.

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
Scheme 1
Scheme 2
Scheme 3
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Sharman WM, Lier JE (2003) In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 15. Academic Press, New York, pp 1–62

  2. Claessens CG, Hahn U, Torres T (2008) Chem Rec 8:75

    Article  CAS  Google Scholar 

  3. de la Torre G, Claessens CG, Torres T (2007) Chem Commun 2000

  4. Snow AW (2003) In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 17, Academic Press: New York, pp 129–176

  5. Rio Y, Rodriguez-Morgade MS, Torres T (2008) Org Biomol Chem 6:1877

    Article  CAS  Google Scholar 

  6. Luk’yanets EA, Nemykin VN (2010) J Porphyr Phthalocyanines 14:1

    Article  Google Scholar 

  7. Zorlu Y, Un İ, Dumoulin F (2009) J Porphyr Phthalocyanines 13:760

    Article  CAS  Google Scholar 

  8. Nemykin VN, Luk’yanets EA (2010) ARKIVOC (i)136–208

  9. Ogunsipe A, Chen JY, Nyokong T (2004) New J Chem 28:822

    Article  CAS  Google Scholar 

  10. Kobayashi N, Ogata H, Nonaka N, Luk’yanets EA (2003) Chem Eur J 9:5123

    Article  CAS  Google Scholar 

  11. Choi MTM, Li PPS, Ng DKP (2000) Tetrahedron 56:3881

    Article  CAS  Google Scholar 

  12. Zorlu Y, Dumoulin F, Durmus M, Ahsen V (2010) Tetrahedron 66:3248

    Article  CAS  Google Scholar 

  13. Dumoulin F, Durmuş M, Ahsen V, Nyokong N (2010) Coord Chem Rev 254:2792

    Article  CAS  Google Scholar 

  14. İşci Ü, Dumoulin F, Ahsen V, Sorokin AB (2010) J Porphyr Phthalocyanines 14:324

    Article  Google Scholar 

  15. Wöhrle D, Eskes M, Shigehara K, Yamada A (1993) Synthesis 194

  16. Gürek AG, Bekaroğlu Ö (1994) J Chem Soc Dalton Trans 1419

  17. Mbambisa G, Tau P, Antunes E, Nyokong T (2007) Polyhedron 26:5355

    Article  CAS  Google Scholar 

  18. Gregory P (2000) J Porphyr Phthalocyanines 4:432

    Article  CAS  Google Scholar 

  19. Wainwright M (2010) Color Technol 126:115

    Article  CAS  Google Scholar 

  20. Qian G, Wang ZY (2010) Chem Asian J 5:1006

    CAS  Google Scholar 

  21. Wang ZY, Zhang J, Wu X, Birau M, Yu G, Yu H, Qi Y, Desjardins P, Meng X, Gao JP, Todd E, Song N, Bai Y, Beaudin AMR, LeClair G (2004) Pure Appl Chem 76:1435

    Article  CAS  Google Scholar 

  22. Burnham PM, Cook MJ, Gerrard LA, Heeney MJ, Hughes DL (2003) Chem Commun 2064

  23. Ogunbayo TB, Nyokong T (2009) Polyhedron 28:2710

    Article  CAS  Google Scholar 

  24. Sakamoto K, Ohno-Okumura E, Kato T, Sogaa H (2010) J Porphyr Phthalocyanines 14:47

    Article  CAS  Google Scholar 

  25. Kostka M, Zimcik P, Miletin M, Klemera P, Kopecky K, Musil Z (2006) J Photochem Photobiol A 178:16

    Article  CAS  Google Scholar 

  26. Zimcik P, Miletin M, Novakova V, Kopecky K, Nejedla M, Stara V, Sedlackova K (2009) Aust J Chem 62:425

    CAS  Google Scholar 

  27. Novakova V, Zimcik P, Miletin M, Kopecky K, Ivincová J (2010) Tetrahedron Lett 51:1016

    Article  CAS  Google Scholar 

  28. Volkov KA, Avramenko GV, Negrimovskii VM, Luk’yanets EA (2007) Russ J Gen Chem 77:1108

    Article  CAS  Google Scholar 

  29. Bruker (2008) APEX2 (Version 2008.1-0). Bruker AXS Inc., Madison

    Google Scholar 

  30. Bruker (2001). SAINT-V6.28A. Data Reduction Software

  31. Sheldrick GM SADABS. Program for empirical absorption correction. University of Göttingen, Germany

  32. Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Grazia A, Moliterni G, Polidori G, Spagna RJ (1999) Appl Cryst 32:115

    Article  CAS  Google Scholar 

  33. Palatinus L, Chapuis GJ (2007) Appl Cryst 40:786

    Article  CAS  Google Scholar 

  34. Betteridge PW, Carruthers JR, Cooper RI, Prout K, Watkin DJJ (2003) Appl Cryst 36:1487

    Article  CAS  Google Scholar 

  35. Volkov KA, Avramenko GV, Negrimovskii VM, Luk’yanets EA (2007) Russ J Gen Chem 77:1126

    Article  CAS  Google Scholar 

  36. Volkov KA, Negrimovskii VM, Avramenko GV, Luk’yanets EA (2008) Russ J Gen Chem 78:1794

    Article  CAS  Google Scholar 

  37. Lo P-C, Cheng DYY, Ng DKP (2005) Synthesis 7:1141

    Google Scholar 

  38. Birchall JWI, Haszeldine RN, Morley JO (1970) J Chem Soc C 456

  39. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The Scientific and Technological Research Council of Turkey TUBITAK (PIA Turkey-France bilateral project Bosphorus 109M356) is gratefully acknowledged. YC thanks the long-life learning Erasmus funding.

Author information

Authors and Affiliations

  1. Department of Chemistry, Gebze Institute of Technology, P. O. Box 141, 41400, Gebze, Kocaeli, Turkey

    Ufuk Kumru, Fabienne Dumoulin, Fatma Yuksel, Yari Cabezas, Yunus Zorlu & Vefa Ahsen

  2. CNRS UMR 5615, Laboratoire des Multimatériaux et Interfaces, Université Lyon1, 69622, Villeurbanne, France

    Erwann Jeanneau

  3. Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Clermont Université, BP 10448, 63000, Clermont-Ferrand, France

    Yari Cabezas

Authors
  1. Ufuk Kumru
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fabienne Dumoulin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Erwann Jeanneau
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fatma Yuksel
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yari Cabezas
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yunus Zorlu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Vefa Ahsen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vefa Ahsen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kumru, U., Dumoulin, F., Jeanneau, E. et al. 4,5-, 3,6-, and 3,4,5,6-tert-Butylsulfanylphthalonitriles: synthesis and comparative structural and spectroscopic analyses. Struct Chem 23, 175–183 (2012). https://doi.org/10.1007/s11224-011-9850-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-011-9850-8

Keywords

Search

Navigation