Skip to main content
Log in

Reactivity of 2,6-Dichloropurine Ribonucleoside Studied by 35Cl NQR Spectroscopy

  • Published:
Applied Magnetic Resonance Aims and scope Submit manuscript

Abstract.

2,6-Dichloropurine ribonucleoside is a precursor in the potential synthesis of anticancer and antiviral drugs. 35Cl nuclear quadrupole resonance (NQR) studies on electronic structure and the character of C–Cl bonds may provide a valuable information about the difference in reactivity of chlorine atoms present in this compound. In this work 35Cl NQR frequencies, asymmetry parameters and double-bond character for both C–Cl bonds have been determined experimentally. These parameters were then compared with the corresponding theoretical values obtained by means of the density functional theory.

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.

Similar content being viewed by others

References

  • Nair, V., Richardson, S.G.: Synthesis 8, 670–672 (1982)

    Article  Google Scholar 

  • Niiya, K., Olsson, R.A., Thompson, R.D., Silivia, S.: J. Med. Chem. 35, 4557–4561 (1992)

    Article  Google Scholar 

  • Thompson, R.D., Secunda, S., Daly, J.W., Olsson, R.A.: J. Med. Chem. 34, 3388–3390 (1991)

    Article  Google Scholar 

  • Lucken, E.A.C.: Nuclear Quadrupole Coupling Constants. Academic Press, London (1969)

    Google Scholar 

  • Francom, P., Robins, M.J.: J. Org. Chem. 68, 666–669 (2003)

    Article  Google Scholar 

  • Bussandri, A.P., Zuriaga, M.J.: J. Magn. Reson. 131, 224–231 (1998)

    Article  ADS  Google Scholar 

  • Harbison, G.S., Slokenbergs, A.: Z. Naturforsch. A 45, 575–580 (1990)

    Google Scholar 

  • Balchin, E., Malcolme-Lawes, D.J., Poplett, I.J.F., Rowe, M.D., Smith, J.A.S., Pearce, G.E.S., Wren, S.A.C.: Anal. Chem. 77, 3925–3930 (2005)

    Article  Google Scholar 

  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, T., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewski, V., Ortiz, J.V., Foresman, J.B., Closlowski, J., Stefanov, B.B., Nanayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, W., Wong, M.W., Andress, J.L., Replogle, E.S., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., Defress, D.J., Baker, J., Stewart, J.P., Head-Gordon, M., Gonzales, C., Pople, J.A.: Gaussian'98, Revision A. Gaussian Inc., Pittsburgh, PA (1998)

    Google Scholar 

  • Perdew, J.P., Burke, K., Wang, Y.: Phys. Rev. B 54, 16533–16539 (1996)

    Article  ADS  Google Scholar 

  • De Proft, F., Martin, J.M.L., Geerlings, P.: Chem. Phys. Lett. 256, 400–408 (1996)

    Article  ADS  Google Scholar 

  • Pyykkö, P.: Mol. Phys. 99, 1617–1629 (2001)

    Article  ADS  Google Scholar 

  • Glendening, E.D., Reed, A.E., Carpenter, J.E., Weinhold, F.: NBO Version 3.1.7

  • Maćkowiak, M., Kątowski, P., Ostafin, M.: J. Mol. Struct. 345, 173–180 (1995)

    Article  ADS  Google Scholar 

  • Bersohn, R.: J. Chem. Phys. 22, 2078–2083 (1954)

    Article  ADS  Google Scholar 

  • Vittori, S., Lorenzen, A., Stannek, C., Costanzi, S., Volpini, R., IJzerman, A.P.: J. Med. Chem. 43, 250–260 (2000)

    Article  Google Scholar 

  • Gundersen, L., Nissen-Meyer, J., Spilsberg, B.: J. Med. Chem. 45, 1383–1386 (2002)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Authors' address: Iwona Dobak, Department of Chemistry, Adam Mickiewicz University, Grunwaldska 6, Poznań 60-780, Poland

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dobak, I., Ostafin, M., Poleshchuk, O. et al. Reactivity of 2,6-Dichloropurine Ribonucleoside Studied by 35Cl NQR Spectroscopy. Appl Magn Reson 34, 47–53 (2008). https://doi.org/10.1007/s00723-008-0091-y

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00723-008-0091-y

Keywords

Navigation