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Theoretical view on structure, chemical reactivity, aromaticity and 14N NQR parameters of iridapyridine isomers

  • Structure and Properties of Coordination Compounds
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Abstract

Using quantum chemical calculations, we report structures, energetics, natural bond analysis, aromaticity and 14N NQR parameters of the irdidapyridine isomers. The MPW1PW91, PBEPBE and PBE1PBE calculations indicate the most stability for meta-isomer. Global electrophilicity index shows that iridapyridines are stronger electrophile rather than pyridine. Local reactivity descriptors as Fukui functions ( f + k , f − k ), local softnesses ( s + k , s − k ) and electrophilicity indices ( ω + k , ω − k ) analyses are performed to find out the reactive sites within molecules. Nucleus-independent chemical shift (NICS) has been evaluated to understand the aromaticity. Also, changes in 14N NQR parameters of the molecules are studied.

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References

  1. J. R. Bleeke, Chem. Rev., 101, 1205–1227 (2001).

    Article  CAS  Google Scholar 

  2. G. He, H. Xia, and G. Jia, Chin. Sci. Bull., 49, 1543–1553 (2004).

    CAS  Google Scholar 

  3. L. J. Wright, J. Chem. Soc., Dalton Trans., 1821–1827 (2006).

    Google Scholar 

  4. J. Chen and G. Jia, Coord. Chem. Rev., 257, 2491–2521 (2013).

    Article  CAS  Google Scholar 

  5. R. Ghiasi, Russ. J. Coord. Chem., 37, 72–76 (2011).

    Article  CAS  Google Scholar 

  6. V. Jacob, C. W. Landorf, L. N. Zakharov, T. J. R. Weakley, and M. M. Haley, Organometallics, 28, 5183–5190 (2009).

    Article  CAS  Google Scholar 

  7. M. Paneque, C. M. Posadas, and M. L. Poveda, J. Am. Chem. Soc., 125, 9898/9899 (2003).

    Article  Google Scholar 

  8. R. D. Gilbertson, T. L. S. Lau, and S. Lanza, Organometallics, 22, 3279–3289 (2003).

    Article  CAS  Google Scholar 

  9. R. D. Gilbertson, T. J. R. Weakley, and M. M. Haley, J. Am. Chem. Soc., 121, 2597/2598 (1999).

    Article  Google Scholar 

  10. R. D. Gilbertson, T. J. R. Weakley, and M. M. Haley, Chem. Eur. J., 6, 437–441 (2000).

    Article  CAS  Google Scholar 

  11. C. W. Landorf and M. M. Haley, Angew. Chem., Int. Ed., 45, 3914–3936 (2006).

    Article  CAS  Google Scholar 

  12. I. Fernandez and G. Frenking, Chem. Eur. J., 13, 5873–5884 (2007).

    Article  CAS  Google Scholar 

  13. M. A. Iron, A. C. B. Lucassen, H. Cohen, M. E. van der Boom, and J. M. L. Martin, J. Am. Chem. Soc., 126, 11699–11710 (2004).

    Article  CAS  Google Scholar 

  14. C. E. F. Rickard, W. R. Roper, S. D. Woodgate, and L. J. Wright, Angew. Chem., Int. Ed., 39, 750–752 (2000).

    Article  CAS  Google Scholar 

  15. G. R. Clark, P. M. Johns, W. R. Roper, and L. J. Wright, Organometallics, 27, 451–454 (2008).

    Article  CAS  Google Scholar 

  16. R. Ghiasi and E. E. Mokarram, Russ. J. Coord. Chem., 37, 463–467 (2011).

    Article  CAS  Google Scholar 

  17. G. R. Clark, P. M. Johns, W. R. Roper, and L. J. Wright, Organometallics, 25, 1771–1177 (2006).

    Article  CAS  Google Scholar 

  18. G. R. Clark, G.-L. Lu, W. R. Roper, and L. J. Wright, Organometallics, 26, 2167–2177 (2007).

    Article  CAS  Google Scholar 

  19. A. F. Dalebrook and L. J. Wright, Organometallics, 28, 5536–5540 (2009).

    Article  CAS  Google Scholar 

  20. T. Wang, S. Li, H. Zhang, R. Lin, F. Han, Y. Lin, T. B. Wen, and H. Xia, Angew. Chem., Int. Ed., 48, 6453–6456 (2009).

    Article  CAS  Google Scholar 

  21. J. Chen, L. M. Daniels, and R. J. Angelici, J. Am. Chem. Soc., 112, 199–204 (1990).

    Article  CAS  Google Scholar 

  22. C. Bianchini, A. Meli, M. Peruzzini, et al., J. Am. Chem. Soc., 115, 2731–2742 (1993).

    Article  CAS  Google Scholar 

  23. C. Bianchini, A. Meli, M. Peruzzini, et al., J. Am. Chem. Soc., 116, 4370–4381 (1994).

    Article  CAS  Google Scholar 

  24. R. Islas, J. Poater, and M. Solà, Organometallics, 33, 1762–1773 (2014).

    Article  CAS  Google Scholar 

  25. R. Hoffmann, Angew. Chem., Int. Ed. Engl., 21, 711–724 (1982).

    Article  Google Scholar 

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

    Google Scholar 

  27. R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople, J. Chem. Phys., 72, 650–654 (1980).

    Article  CAS  Google Scholar 

  28. A. J. H. Wachters, J. Chem. Phys., 52, 1033 (1970).

    Article  CAS  Google Scholar 

  29. P. J. Hay, J. Chem. Phys., 66, 4377–4384 (1977).

    Article  CAS  Google Scholar 

  30. A. D. McLean and G. S. Chandler, J. Chem. Phys., 72, 5639–5648 (1980).

    Article  CAS  Google Scholar 

  31. P. J. Hay and W. R. Wadt, J. Chem. Phys., 82, 299–310 (1985).

    Article  CAS  Google Scholar 

  32. P. J. Hay and W. R. Wadt, J. Chem. Phys., 82, 284–298 (1985).

    Article  Google Scholar 

  33. A. Schaefer, H. Horn, and R. Ahlrichs, J. Chem. Phys., 97, 2571–2577 (1992).

    Article  CAS  Google Scholar 

  34. D. Figgen, K. A. Peterson, M. Dolg, and H. Stoll, J. Chem. Phys., 130, 164108 (2009).

    Article  Google Scholar 

  35. C. Adamo and V. Barone, J. Chem. Phys., 108, 664–675 (1998).

    Article  CAS  Google Scholar 

  36. J. P. C. A. M. Porembski and J. C. Weisshaar, J. Phys. Chem. A, 105, 4851 (2001).

    Article  CAS  Google Scholar 

  37. M. Porembski and J. C. Weisshaar, J. Phys. Chem. A, 105, 6655–6667 (2001).

    Article  CAS  Google Scholar 

  38. Y. Zhang, Z. Guo, and X.-Z. You, J. Am. Chem. Soc., 123, 9378–9387 (2001).

    Article  CAS  Google Scholar 

  39. R. C. Dunbar, J. Phys. Chem. A, 106, 7328–7337 (2002).

    Article  CAS  Google Scholar 

  40. C. Adamo and V. Barone, J. Chem. Phys., 110, 6158–6170 (1999).

    Article  CAS  Google Scholar 

  41. J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 77, 3865–3868 (1996).

    Article  CAS  Google Scholar 

  42. A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 88, 899–926 (1988).

    Article  CAS  Google Scholar 

  43. E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Weinhold, in: Gaussian Inc., Pittsburg, PA (2003).

    Google Scholar 

  44. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, and P. v. R. Schleyer, Chem. Rev., 105, 3842–3888 (2005).

    Article  CAS  Google Scholar 

  45. J. J. Torres-Vega, A. V-Espinal, J. Caballero, M. L. Valenzuela, L. A. Thon, E. Osorio, and W. Tiznado, Inorg. Chem., 53, 3579–3585 (2014).

    Article  CAS  Google Scholar 

  46. R. Islas, G. M. Guajardo, J. O. C. Jiménez-Halla, M. Sola, and G. Merino, J. Chem. Theory Comput., 6, 1131–1135 (2010).

    Article  CAS  Google Scholar 

  47. J. J. Torres, R. Islas, E. Osorio, J. G. Harrison, W. Tiznado, and G. Merino, J. Phys. Chem. A, 117, 5529–5533 (2013).

    Article  CAS  Google Scholar 

  48. P. v. R. Schleyer, C. Marker, A. Dransfeld, H. Jiao, and N. J. R. V. Hommes, J. Am. Chem. Soc., 118, 6317/6318 (1996).

    Google Scholar 

  49. P. v. R. Schleyer, M. Monohar, Z. Wang, B. Kiran, H. Jiao, R. Puchta, and N. J. R. V. Hommes, Org. Lett., 3, 2465–2468 (2001).

    Article  CAS  Google Scholar 

  50. C. Corminboeuf, T. Heine, G. Seifert, P. v. R. Schleyer, and J. Weber, Phys. Chem. Chem. Phys., 6, 273–276 (2004).

    Article  CAS  Google Scholar 

  51. H. Fallah-Bagher-Shaidaei, C. S. Wannere, C. Corminboeuf, R. Puchta, and P. v. R. Schleyer, Org. Lett., 8, 863–866 (2006).

    Article  CAS  Google Scholar 

  52. K. Wolinski, J. F. Hinton, and P. Pulay, J. Am. Chem. Soc., 112, 8251–8260 (1990).

    Article  CAS  Google Scholar 

  53. J. D. Graybeal, Molecular Spectroscopy, McGraw-Hill (1988).

    Google Scholar 

  54. J. Seliger, Nuclear Quadrupole Resonance, Theory–Encyclopedia of Spectroscopy and Spectrometry, Academic Press (2000).

    Google Scholar 

  55. C. P. Slichter, Principles of Magnetic Resonance, 3rd ed., Springer-Verlag, Heidelberg (1990).

    Book  Google Scholar 

  56. P. Pyykko, Mol. Phys., 99, 1617–1629 (2001).

    Article  CAS  Google Scholar 

  57. J. E. Huheey, E. A. Keiter, and R. L. Keiter, Inorganic Chemistry, Principles of Structure and Reactivity, 4th ed., Harper and Row, New York (1994).

    Google Scholar 

  58. J. R. Bleeke, Y.-F. Xie, W.-J. Peng, and M. Chiang, J. Am. Chem. Soc., 111, 4118–4120 (1989).

    Article  CAS  Google Scholar 

  59. R. G. Pearson, J. Org. Chem., 54, 1430–1432 (1989).

    Article  Google Scholar 

  60. R. G. Parr and R. G. Pearson, J. Am. Chem. Soc., 105, 7512–7516 (1983).

    Article  CAS  Google Scholar 

  61. P. Geerling, F. D. Proft, and W. Langenaeker, Chem. Rev., 103, 1793–1874 (2003).

    Article  Google Scholar 

  62. R. G. Parr, L. v. Szentpály, and S. Liu, J. Am. Chem. Soc., 121, 1922–1924 (1999).

    Article  CAS  Google Scholar 

  63. P. K. Chattaraj, U. Sarkar, and D. R. Roy, Chem. Rev., 106, 2065–2091 (2006).

    Article  CAS  Google Scholar 

  64. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, New York (1989).

    Google Scholar 

  65. W. Yang and W. J. Mortier, J. Am. Chem. Soc., 108, 5708–5711 (1986).

    Article  CAS  Google Scholar 

  66. K. B. Wiberg, Tetrahedron, 24, 1083 (1968).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Basic Science, East Tehran Branch, Islamic Azad University, Qiam Dasht, Tehran, Iran

    R. Ghiasi & E. Amini

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  1. R. Ghiasi
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  2. E. Amini
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Original Russian Text © 2015 R. Ghiasi, E. Amini.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 8, pp. 1522-1531, December, 2015.

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Ghiasi, R., Amini, E. Theoretical view on structure, chemical reactivity, aromaticity and 14N NQR parameters of iridapyridine isomers. J Struct Chem 56, 1458–1467 (2015). https://doi.org/10.1134/S0022476615080028

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