Skip to main content
SpringerLink
Log in

Quantum-chemical study on adenine nitrosonium complexes

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Adenine complexes with nitrosonium ion have been studied by the RI-MP2/L1 quantum-chemical method. Addition of nitrosonium ion to adenine tautomers produces a set of nitrosonium complexes of different types (1η–3η). n-Complexes involving NO+ coordination to nitrogen atoms are more energetically favorable than π-complexes. The global minimum on the potential energy surface is occupied by the complex of 7H-adenine tautomer with nitrosonium ion coordinated at the N3 atom.

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

Similar content being viewed by others

References

  1. Hayat, S., Hasan, S.A., Mori, M., Fariduddin, Q., and Ahmad, A., Nitric Oxide in Plant Physiology, Hayat, S., Mori, M., Pichtel, J., and Ahmad, A., Eds., Weinheim: Wiley-VCH, 2010, p. 1.

    Google Scholar 

  2. Vanin, A.F., Ross. Khim. Zh., 2009, vol. 53, no. 6, p. 70.

    CAS  Google Scholar 

  3. Stojanović, S., Stanić, D., Nikolić, M., Spasić, M., and Niketić, V., Nitric Oxide, 2004, vol. 11, p. 256.

    Article  Google Scholar 

  4. Lipton, S.A., Choi, Y.-B., Pan, Z.-H., Lei, S.Z., Chen, H.-S.V., Sucher, N.J., Loscalzo, J., Singel, D.J., and Stamler, J.S., Nature, 1993, vol. 364, p. 626.

    Article  CAS  Google Scholar 

  5. Stamler, J.S., Singel, D.J., and Loscalzo, J., Science, 1992, vol. 258, p. 1898.

    Article  CAS  Google Scholar 

  6. Kirchner, J.J., Sigurdsson, S.Th., and Hopkins, P.B., J. Am. Chem. Soc., 1992, vol. 114, p. 4021.

    Article  CAS  Google Scholar 

  7. Elcock, A.H., Lyne, P.D., Mulholland, A.J., Nandra, A., and Richards, W.G., J. Am. Chem. Soc., 1995, vol. 117, p. 4706.

    Article  CAS  Google Scholar 

  8. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2011, vol. 47, p. 1703.

    Article  CAS  Google Scholar 

  9. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 52.

    Article  CAS  Google Scholar 

  10. Andreev, R.V., Borodkin, G.I., and Shubin, V.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1216.

    Article  CAS  Google Scholar 

  11. Trygubenko, S.A., Bogdan, T.V., Rueda, M., Orozso, M., Luque, F.J., Šponer, J., Slavíček, P., and Hobza, P., Phys. Chem. Chem. Phys., 2002, vol. 4, p. 4192.

    Article  CAS  Google Scholar 

  12. Hanus, M., Kabeláč, M., Rejnek, J., Ryjáček, F., and Hobza, P., J. Phys. Chem. B, 2004, vol. 108, p. 2087.

    Article  CAS  Google Scholar 

  13. Hobza, P. and Šponer, J., J. Am. Chem. Soc., 2002, vol. 124, p. 11 802.

    Article  CAS  Google Scholar 

  14. Jurečka, P. and Hobza, P., J. Am. Chem. Soc., 2003, vol. 125, p. 15 608; Šponer, J., Jurečka, P., and Hobza, P., J. Am. Chem. Soc., 2004, vol. 126, p. 10 142.

    Google Scholar 

  15. Kabeláč, M. and Hobza, P., J. Phys. Chem. B, 2006, vol. 110, p. 14 515.

    Google Scholar 

  16. Katritzky, A.R. and Karelson, M., J. Am. Chem. Soc., 1991, vol. 113, p. 1561.

    Article  CAS  Google Scholar 

  17. Schreiber, M. and González, L., J. Comput. Chem., 2007, vol. 28, p. 2299.

    Article  CAS  Google Scholar 

  18. Huang, R., Zhao, L.-B., Wu, D.-Y., and Tian, Z.-Q., J. Phys. Chem. C, 2011, vol. 115, p. 13 739.

    CAS  Google Scholar 

  19. Saha, S., Wang, F., and Brunger, M.J., Mol. Simul., 2006, vol. 32, p. 1261.

    Article  CAS  Google Scholar 

  20. Russo, N., Toscano, M., and Grand, A., J. Phys. Chem. B, 2001, vol. 105, p. 4735.

    Article  CAS  Google Scholar 

  21. Guerra, C.F., Bickelhaupt, F.M., Saha, S., and Wang, F., J. Phys. Chem. A, 2006, vol. 110, p. 4012.

    Article  CAS  Google Scholar 

  22. Kim, H.-S., Ahn, D.-S., Chung, S.-Y., Kim, S.K., and Lee, S., J. Phys. Chem. A, 2007, vol. 111, p. 8007.

    Article  CAS  Google Scholar 

  23. Salter, L.M. and Chaban, G.M., J. Phys. Chem. A, 2002, vol. 106, p. 4251.

    Article  CAS  Google Scholar 

  24. Plützer, Ch. and Kleinermanns, K., Phys. Chem. Chem. Phys., 2002, vol. 4, p. 4877.

    Article  Google Scholar 

  25. Van Zundert, G.C.P., Jaeqx, S., Berden, G., Bakker, J.M., Kleinermanns, K., Oomens, J., and Rijs, A.M., Chem. Phys. Chem., 2011, vol. 12, p. 1921.

    Article  Google Scholar 

  26. Burova, T.G., Ermolenkov, V.V., Ten, G.N., Shcherbakov, R.S., Baranov, V.I., and Lednev, I.K., J. Phys. Chem. A, 2011, vol. 115, p. 10 600.

    Article  CAS  Google Scholar 

  27. Laxer, A., Major, D.T., Gottlieb, H.E., and Fischer, B., J. Org. Chem., 2001, vol. 66, p. 5463.

    Article  CAS  Google Scholar 

  28. Aidas, K., Mikkelsen, K.V., and Kongsted, J., Phys. Chem. Chem. Phys., 2010, vol. 12, p. 761; Nowak, M.J., Lapinski, L., Kwiatkowski, J.S., and Leszczyński, J., J. Phys. Chem., 1996, vol. 100, p. 3527.

    Article  CAS  Google Scholar 

  29. Vogt, N., Dorofeeva, O.V., Sipachev, V.A., and Rykov, A.N., J. Phys. Chem. A, 2009, vol. 113, p. 13 816.

    CAS  Google Scholar 

  30. Mahapatra, S., Nayak, S.K., Prathapa, S.J., and Row, T.N.G., Cryst. Growth Des., 2008, vol. 8, p. 1223.

    Article  CAS  Google Scholar 

  31. Taylor, R. and Kennard, O., J. Mol. Struct., 1982, vol. 78, p. 1.

    Article  CAS  Google Scholar 

  32. Donohue, J., Archiv. Biochem. Biophys., 1968, vol. 128, p. 591.

    Article  CAS  Google Scholar 

  33. Rosokha, S.V. and Kochi, J.K., J. Am. Chem. Soc., 2001, vol. 123, p. 8985.

    Article  CAS  Google Scholar 

  34. Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, p. 936.

    CAS  Google Scholar 

  35. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. S1.

  36. Borodkin, G.I. and Shubin, V.G., Usp. Khim., 2001, vol. 70, p. 241.

    Article  Google Scholar 

  37. Feyereisen, M., Fitzgerald, G., and Komornicki, A., Chem. Phys. Lett., 1993, vol. 208, p. 359.

    Article  CAS  Google Scholar 

  38. Laikov, D.N., Chem. Phys. Lett., 1997, vol. 281, p. 151; Laikov, D.N. and Ustynyuk, Yu.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2005, p. 804.

    Article  CAS  Google Scholar 

  39. Minkin, V.I., Simkin, B.Ya., and Minyaev, R.M., Kvantovaya khimiya organicheskikh soedinenii. Mekhanizmy reaktsii (Quantum Chemistry of Organic Compounds. Reaction Mechanisms), Moscow: Khimiya, 1986.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    R. V. Andreev, G. I. Borodkin & V. G. Shubin

Authors
  1. R. V. Andreev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. I. Borodkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. G. Shubin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. I. Borodkin.

Additional information

Original Russian Text © R.V. Andreev, G.I. Borodkin, V.G. Shubin, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1342–1349.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Andreev, R.V., Borodkin, G.I. & Shubin, V.G. Quantum-chemical study on adenine nitrosonium complexes. Russ J Org Chem 48, 1337–1344 (2012). https://doi.org/10.1134/S1070428012100144

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428012100144

Keywords

Search

Navigation