Skip to main content
SpringerLink
Log in

Chiral distinction in square planar Pt and Pd complexes of 2,2′-bipyridine derivatives

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

Abstract

A computational study of square planar organometallic complexes formed by the ligand 2,2′-bipyridine and all its possible difluoro derivatives in analogous position of the aromatic rings (n,n′-difluoro-2,2′-bipyridine, where n = n′ = 3, 4, 5, and 6) and two M–X2 (M = Pd and Pt and X = F, Cl, Br, and I) fragments has been carried out amounting to a total of 80 complexes. Relationships have been found between the chiral distinction energy and the different chemical moieties present. Using the statistical Free-Wilson method, the relative energies between the diastereomeric complexes have been correlated with the position of the substituent, the counter anion, and the central metal cation.

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

Similar content being viewed by others

References

  1. Amouri H, Gruselle M (2008) Chirality in transition metal chemistry: molecules, supramolecular assemblies and materials. Wiley, Chippenham, UK

    Google Scholar 

  2. Maseras F, Lledos A (2002) Computational modeling of homogeneous catalysis. Kluwer, New York

    Book  Google Scholar 

  3. Girard C, Kagan HB (1998) Angew Chem Int Ed 37:2922

    Article  Google Scholar 

  4. Yamakawa M, Noyori R (1995) J Am Chem Soc 117:6327

    Article  CAS  Google Scholar 

  5. Speranza M (2004) Adv Phys Org Chem 39:147

    Article  CAS  Google Scholar 

  6. Tao WA, Zhang DX, Nikolaev EN, Cooks RG (2000) J Am Chem Soc 122:10598

    Article  CAS  Google Scholar 

  7. Paladini A, Calcagni C, Di Palma T, Speranza M, Lagana A, Fago G, Filippi A, Satta M, Guidoni AG (2001) Chirality 13:707

    Article  CAS  Google Scholar 

  8. Folmer-Andersen JF, Lynch VM, Anslyn EV (2005) J Am Chem Soc 127:7986

    Article  CAS  Google Scholar 

  9. Cucciolito ME, Flores G, Vitagliano A (2004) Organometallics 23:15

    Article  CAS  Google Scholar 

  10. Jodry JJ, Frantz R, Lacour J (2004) Inorg Chem 43:3329

    Article  CAS  Google Scholar 

  11. Chow HS, Constable EC, Frantz R, Housecroft CE, Lacour J, Neuburger M, Rappoport D, Schaffner S (2009) New J Chem 33:376

    Article  CAS  Google Scholar 

  12. Alkorta I, Picazo O, Elguero J (2005) J Phys Chem A 109:9573

    Article  CAS  Google Scholar 

  13. Rozas I, Alkorta I, Elguero J (2006) J Phys Chem A 110:13310

    Article  CAS  Google Scholar 

  14. Picazo O, Alkorta I, Elguero J, Sundberg MR, Valo J (2007) Eur J Inorg Chem 324

  15. Picazo O, Alkorta I, Elguero J, Sundberg MR (2006) Inorg Chem Commun 9:712

    Article  CAS  Google Scholar 

  16. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  17. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  18. Hay PJ, Wadt WR (1985) J Chem Phys 82:299

    Article  CAS  Google Scholar 

  19. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala P Y, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98. Gaussian Inc, Pittsburgh, PA

  20. Frisch MJ Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03. Gaussian Inc, Pittsburgh, PA

  21. Bader RFW (1990) Atoms in molecules a quantum theory. Oxford University, New York

    Google Scholar 

  22. Biegler-König FW, Bader RFW, Tang TH (1982) J Comput Chem 3:317

    Article  Google Scholar 

  23. Biegler-König FW, Schönbom J (2002) AIM2000, 2nd edn. Bielefeld, Germany

  24. CSD database version 5.30 (November 2008)

  25. Montet Y, Kozelka J (1999) Inorg Chim Acta 284:103

    Article  CAS  Google Scholar 

  26. Agranat I, Sarel S (1996) Enantiomer 1:249

    CAS  Google Scholar 

  27. Free SM, Wilson JW (1964) J Med Chem 7:395

    Article  CAS  Google Scholar 

  28. Alkorta I, Blanco F, Elguero J (2008) Tetrahedron 64:3826

    Article  CAS  Google Scholar 

  29. Nabavizadeh SM, Rashidi M (2007) Polyhedron 26:1476

    Article  CAS  Google Scholar 

  30. Aue DH, Webb HM, Davidson WR, Toure P, Hopkins HP Jr, Moulik SP, Jahagirdar DV (1991) J Am Chem Soc 113:1770

    Article  CAS  Google Scholar 

  31. Alkorta I, Elguero J (2004) Struct Chem 15:117

    Article  CAS  Google Scholar 

  32. Matta CF, Castillo N, Boyd RJ (2005) J Phys Chem A 109:3669

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was carried out with financial support from the Ministerio de Educación y Ciencia (Projects No. CTQ2007-61901/BQU) and Comunidad Autónoma de Madrid (Project MADRISOLAR, ref. S-0505/PPQ/0225). We thank the CTI (CSIC) for computational facilities.

Author information

Authors and Affiliations

  1. Instituto de Química Médica (C.S.I.C.), Juan de la Cierva, 3, 28006, Madrid, Spain

    Oscar Picazo, Ibon Alkorta & José Elguero

  2. Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), Helsinki, 00014, Finland

    Markku R. Sundberg & Jaana Valo

  3. Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060, Krakow, Poland

    Krzysztof Zborowski

Authors
  1. Oscar Picazo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ibon Alkorta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. José Elguero
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Markku R. Sundberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jaana Valo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Krzysztof Zborowski
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Ibon Alkorta or Markku R. Sundberg.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Picazo, O., Alkorta, I., Elguero, J. et al. Chiral distinction in square planar Pt and Pd complexes of 2,2′-bipyridine derivatives. Struct Chem 20, 557–563 (2009). https://doi.org/10.1007/s11224-009-9463-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-009-9463-7

Keywords

Search

Navigation