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Quantum chemical calculations of NMR chemical shifts of organic molecules: XI. Conformational and relativistic effects on the 31P and 77Se chemical shifts of phosphine selenides

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Abstract

Conformational and relativistic effects on the 31P and 77Se chemical shifts of phosphine selenides were analyzed in terms of the ZORA-GIAO-B1PW91/TZP approach. The effect of conformation of phosphine selenides related to internal rotation about the single P-C bonds was found to be insignificant, while the contribution of relativistic spin-orbit interaction to the calculated values of 77Se chemical shifts did not exceed 10 ppm. On the other hand, relativistic effects arising from magnetic shielding of the phosphorus nucleus in the P=Se fragment by selenium are fairly strong (25–30 ppm), which indicates the necessity of including the contribution of relativistic spin-orbit interaction in the calculation of 31P chemical shifts in phosphine selenides.

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References

  1. Chernyshev, K.A., Gostevskii, B.A., and Krivdin, L.B., Russ. J. Org. Chem., 2013, vol. 49, p. 832.

    Article  CAS  Google Scholar 

  2. Pyykkö, P., Chem. Rev., 1988, vol. 88, p. 563; Pyykkö, P. and Desclaux, J.P., Acc. Chem. Res., 1979, vol. 12, p. 276.

    Article  Google Scholar 

  3. Vaara, J., Manninen, P., and Lantto, P., Calculation of NMR and EPR Parameters. Theory and Applications, Kaupp, M., Buhl, M., and Malkin, V.G., Eds., Weinheim: Wiley-VCH, 2004, p. 209; Autschbach, J., ibid., p. 227.

  4. Helgaker, T., Jaszuński, M., and Ruud, K., Chem. Rev., 1999, vol. 99, p. 293.

    Article  CAS  Google Scholar 

  5. Chernyshev, K.A. and Krivdin, L.B., Russ. J. Org. Chem., 2011, vol. 47, p. 355; Chernyshev, K.A., Larina, L.I., Chirkina, E.A., Rozinov, V.G., and Krivdin, L.B., Russ. J. Org. Chem., 2011, vol. 47, p. 1859; Chernyshev, K.A., Larina, L.I., Chirkina, E.A., Rozinov, V.G., and Krivdin, L.B., Russ. J. Org. Chem., 2011, vol. 47, p. 1865; Chernyshev, K.A. and Krivdin, L.B., Russ. J. Org. Chem., 2012, vol. 48, p. 1518; Chernyshev, K.A., Larina, L.I., Chirkina, E.A., and Krivdin, L.B., Magn. Reson. Chem., 2012, vol. 50, p. 120.

    Article  CAS  Google Scholar 

  6. Pyykkö, P., Görling, A., and Rösch, N., Mol. Phys., 1987, vol. 61, p. 195.

    Article  Google Scholar 

  7. Edlund, U., Lejon, T., Pyykkö, P., Venkatachalam, T.K., and Buncel, E., J. Am. Chem. Soc., 1987, vol. 109, p. 5982.

    Article  CAS  Google Scholar 

  8. Kaupp, M., Aubauer, C., Engelhardt, G., Klapötke, T.M., and Malkina, O.L., J. Chem. Phys., 1999, vol. 110, p. 3897; Fukawa, S., Hada, M., Fukuda, R., Tanaka, S., and Nakatsuji, H., J. Comput. Chem., 2001, vol. 22, p. 528.

    Article  CAS  Google Scholar 

  9. Arbuzova, S.N., Gusarova, N.K., and Trofimov, B.A., Arkivoc, 2006, part (v), p. 12; Trofimov, B.A. and Gusarova, N.K., Mendeleev Commun., 2009, vol. 19, p. 295; Gusarova, N.K., Arbuzova, S.N., and Trofimov, B.A., Pure Appl. Chem., 2012, vol. 84, p. 439.

    Google Scholar 

  10. Malysheva, S.F. and Arbuzova, S.N., Sovremennyi organicheskii sintez (Modern Organic Synthesis), Rakhmankulov, D.L., Ed., Moscow: Khimiya, 2003, p. 160; Sukhov, B.G., Malysheva, S.F., Vakul’skaya, T.I., Tirsky, V.V., Martynovich, E.F., Smetannikov, Yu.V., and Tarasova, N.P., Arkivoc, 2003, part (xiii), p. 196; Smetannikov, Yu.V., Doctoral (Chem.) Dissertation, Moscow, 2005; Tarasova, N.P., Zanin, A.A., Smetannikov, Y.V., and Vilesov, A.S., C. R. Chim., 2010, vol. 13, p. 1028.

  11. Lobana, T.S., Mahajan, R., and Castineiras, A., Transition Met. Chem., 2001, vol. 26, p. 440; Han, H. and Johnson, S.A., Organometallics, 2006, vol. 25, p. 5594; Kling, C., Ott, H., Schwab, G., and Stalke, D., Organometallics, 2008, vol. 27, p. 5038; Arbuzova, S.N., Volkov, P.A., Ivanova, N.I., Gusarova, N.K., Larina, L.I., Kazheva, O.N., Alexandrov, G.G., Dyachenko, O.A., and Trofimov, B.A., J. Organomet. Chem., 2011, vol. 696, p. 2053.

    Article  CAS  Google Scholar 

  12. Bwembya, G.C., Song, X., and Bochmann, M., Chem. Vap. Deposition, 1995, vol. 1, p. 78; Song, X. and Bochmann, M., Dalton Trans., 1997, p. 2689; Fan, D., Afzaal, M., Mallik, M.A., Nguyen, C.Q., O’Brien, P., and Thomas, J.P., Coord. Chem. Rev., 2007, vol. 251, p. 1878; Artem’ev, A.V., Gusarova, N.K., Malysheva, S.F., and Trofimov, B.A., Org. Prep. Proced. Int., 2011, vol. 43, p. 381.

    Article  CAS  Google Scholar 

  13. Matolcsy, G., Nádasy, M., and Andriska, V., Pesticide Chemistry, Amsterdam: Elsevier, 1988; Dehghanpour, S., Rasmi, Y., and Bagheri, M., Mol. Diversity, 2007, vol. 11, p. 47.

    Google Scholar 

  14. Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium, Devillanova, F., Ed., Cambridge: Royal Soc. Chem., 2007, p. 894; Gusarova, N.K., Kuimov, V.A., Malysheva, S.F., Belogorlova, N.A., Albanov, A.I., and Trofimov, B.A., Tetrahedron, 2012, vol. 68, p. 9218; Oparina, L.A., Gusarova, N.K., Vysotskaya, O.V., Kolyvanov, N.A., Artem’ev, A.V., and Trofimov, B.A., Synthesis, 2012, vol. 44, p. 2938.

    Google Scholar 

  15. Dybiec, K. and Gryff-Keller, A., Magn. Reson. Chem., 2009, vol. 47, p. 63; Maryasin, B. and Zipse, H., Phys. Chem. Chem. Phys., 2011, vol. 13, p. 5150.

    Article  CAS  Google Scholar 

  16. Sukhov, B.G., Gusarova, N.K., Ivanova, N.I., Bogdanova, M.V., Kazheva, O.N., Aleksandrov, G.G., D’yachenko, O.A., Sinegovskaya, L.M., Malysheva, S.F., and Trofimov, B.A., Zh. Strukt. Khim., 2005, vol. 46, p. 1066.

    CAS  Google Scholar 

  17. Vereshchagina, Ya.A., Ishmaeva, E.A., and Zverev, V.V., Usp. Khim., 2005, vol. 74, p. 323.

    Article  Google Scholar 

  18. Chernyshev, K.A. and Krivdin, L.B., Russ. J. Org. Chem., 2010, vol. 46, p. 785.

    Article  CAS  Google Scholar 

  19. Trofimov, B.A., Gusarova, N.K., Arbuzova, S.N., Ivanova, N.I., Artem’ev, A.V., Volkov, P.A., Ushakov, I.A., Malysheva, S.F., and Kuimov, V.A., J. Organomet. Chem., 2009, vol. 694, p. 677; Gusarova, N.K., Volkov, P.A., Ivanova, N.I., Larina, L.I., and Trofimov, B.A., Tetrahedron Lett., 2011, vol. 52, p. 2367; Gusarova, N.K., Volkov, P.A., Ivanova, N.I., Larina, L.I., and Trofimov, B.A., Synthesis, 2011, vol. 22, p. 3723.

    Article  CAS  Google Scholar 

  20. Laikov, D.N. and Ustynyuk, Yu.A., Izv. Akad. Nauk, Ser. Khim., 2005, p. 804.

    Google Scholar 

  21. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision C.01, Wallingford CT: Gaussian, 2009.

    Google Scholar 

  22. ADF2009.01, SCM, Theoretical Chemistry, Amsterdam, The Netherlands: Vrije Universiteit; http://www.scm.com

  23. Klamt, A. and Schüürmann, G., J. Chem. Soc., Perkin Trans. 2, 1993, p. 799; Klamt, A., J. Phys. Chem., 1995, vol. 99, p. 2224.

    Google Scholar 

  24. Wolff, S.K., Ziegler, T., van Lenthe, E., and Baerends, E.J., J. Chem. Phys., 1999, vol. 110, p. 7689; Fukui, H. and Baba, T., J. Chem. Phys., 2002, vol. 117, p. 7836.

    Article  CAS  Google Scholar 

  25. Wüllen, C.V., Phys. Chem. Chem. Phys., 2000, vol. 2, p. 2137.

    Article  Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    K. A. Chernyshev, L. B. Krivdin, S. V. Fedorov, S. N. Arbuzova & N. I. Ivanova

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  1. K. A. Chernyshev
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  2. L. B. Krivdin
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  3. S. V. Fedorov
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  4. S. N. Arbuzova
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  5. N. I. Ivanova
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Correspondence to K. A. Chernyshev.

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Original Russian Text © K.A. Chernyshev, L.B. Krivdin, S.V. Fedorov, S.N. Arbuzova, N.I. Ivanova, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 10, pp. 1443–1450.

For communication X, see [1].

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Chernyshev, K.A., Krivdin, L.B., Fedorov, S.V. et al. Quantum chemical calculations of NMR chemical shifts of organic molecules: XI. Conformational and relativistic effects on the 31P and 77Se chemical shifts of phosphine selenides. Russ J Org Chem 49, 1420–1427 (2013). https://doi.org/10.1134/S1070428013100035

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