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Molecular structure of azachalcogenenes with aromatic substituents

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The molecular structure of acyclic and cyclic azachalcogenenes with aromatic substituents is analyzed and compared with related compounds using the data of XRD, NMR, and quantum chemical calculations.

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References

  1. K. Raghavachari and R. C. Haddon,J. Phys. Chem.,87, No. 8, 1308–1312 (1983).

    Article  CAS  Google Scholar 

  2. R. D. Suenram, F. J. Lovas, and W. J. Stevens,J. Mol. Spectrosc.,112, 482–493 (1985).

    Article  CAS  Google Scholar 

  3. J. Kuyper, P. H. Isselmann, F. C. Mylhoff, et al.,J. Mol. Struct.,29, No. 2, 247–252 (1975).

    Article  CAS  Google Scholar 

  4. D. G. Anderson, H. E. Robertson, D. W. H. Rankin, and J. D. Woollins,J. Chem. Soc., Dalton Trans., No. 5, 859–862 (1989).

    Google Scholar 

  5. M. Herberhold, S. Gerstmann, B. Wrakmeyer, and H. Borrmann,ibid., No. 5, 633–636 (1994).

  6. G. Leandri, V. Busetti, G. Valle, and M. Mammi,J. Chem. Soc., Chem. Commun., 413–414 (1970).

  7. V. Busetti,Acta Crystallogr. B,38,665–667 (1982).

    Article  Google Scholar 

  8. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev,Mendeleev Commun., No. 4, 136–137 (1994).

  9. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev,ibid., No. 5, 167–169 (1994).

  10. A. Gieren and F. Pertlick,Abstracts from the 2nd European Crystallography Meeting, Keszthely, Hungary (1974), p. 303.

    Google Scholar 

  11. H. Muensterer, G. Kresze, V. Lamm, and A. Gieren,J. Org. Chem., 48, No. 17, 2833–2837 (1983).

  12. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev,Zh. Strukt. Khim.,37, No. 2, 236–237 (1996).

    Google Scholar 

  13. R. Jones, D. J. Williams, P. T. Wood, and J. D. Woollins,Polyhedron,8, No. 1, 91–96 (1989).

    Article  CAS  Google Scholar 

  14. A. V. Zibarev, Yu. V. Gatilov, I. Yu. Bagryanskaya, and S. N. Konchenko,ibid.,11, No. 21, 2787–2793 (1992).

    CAS  Google Scholar 

  15. J. Leitch, S. C. Nyburg, D. A. Armitage, and M. J. Clark,J. Cryst Mol Struct,3, 337–342 (1973).

    Article  CAS  Google Scholar 

  16. F. P. Olsen and J. C. Barrick,Inorg. Chem.,12, No. 6, 1353–1355 (1973).

    Article  CAS  Google Scholar 

  17. E. M. Holt, S. L. Holt, and K. J. Watson,J. Chem. Soc., Dalton Trans., No. 12, 1357–1360 (1974).

  18. W. Isenberg, R. Mews, and G. M. Sheldrick, Z.Anorg. Allg. Chem., 525, 54–66 (1985).

  19. A. V. Zibarev, A. O. Miller, Yu. V. Gatilov, and G. G. Furin,Heteroatom. Chem.,1, No. 6, 443–453 (1990).

    Article  CAS  Google Scholar 

  20. H. W. Roesky, J. Sundermeyer, M. Noltemeyer, et al., Z.Naturforsch. B,41b, No. 1, 53–58 (1986).

    CAS  Google Scholar 

  21. M. Witt, H. W. Roesky, M. Noltemeyer, et al.,Angew Chem.,93, No. 11, 1017–1018 (1981).

    Google Scholar 

  22. G. MacLean, J. Passmore, P. S. White, et al.,Can. J. Chem.,59, No. 2, 187–190 (1981).

    Article  CAS  Google Scholar 

  23. R. Steudel, J. Steidel, and N. Rautenberg,Z Naturforsch. B,35b, No. 7, 792–796 (1980).

    CAS  Google Scholar 

  24. M. M. Labes, P. Love, and L. F. Nichols,Chem. Rev.,79, No. 1, 1–15 (1979).

    Article  CAS  Google Scholar 

  25. H. S. Rzepa and J. D. Woollins,J. Chem. Soc., Dalton Trans., No. 12, 3051–3053 (1988).

  26. R. M. Bannister and H. S. Rzepa,ibid., No. 8, 1609–1611 (1989).

  27. N. Ya. Derkach and E. S. Levchenko,Usp. Khim.,58, No. 5, 862–879 (1989).

    CAS  Google Scholar 

  28. M. Herberhold and W. Jellen,Z. Naturforsch. B,41b, 144–148 (1988).

    Google Scholar 

  29. T. Chivers, X. Gao, and M. Parvez,J. Chem. Soc., Chem. Commun., No. 18, 2149–2150 (1994).

  30. M. Charton,J. Am. Chem. Soc.,91, No. 3, 615–618 (1969).

    Article  CAS  Google Scholar 

  31. P. Ganis, G. Avitabile, E. Benedetti, et al.,Proc Natl. Acad. Sci. USA,67, No. 1, 426–433 (1970).

    Article  CAS  Google Scholar 

  32. A. V. Zibarev, Yu. V. Gatilov, I. Yu. Bagryanskaya, et al.,J. Chem. Soc., Chem. Commun., No. 3, 298–299 (1993).

    Google Scholar 

  33. R. Filler,Mol. Struct. Energ.,8, 19–41 (1988).

    CAS  Google Scholar 

  34. T. Dahl,Acta Chem. Scand.,48, No. 1, 95–106 (1994).

    Article  CAS  Google Scholar 

  35. F. Cozzi and J. S. Siegel,Pure Appl. Chem.,67, No. 5, 683–689 (1995).

    Article  CAS  Google Scholar 

  36. A. V. Zibarev, Chemical Sciences Doctoral Dissertation, Novosibisrk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk (1996).

  37. M. Herberhold, W. Jellen, W. Buehlmeyer, et al.,Z Naturforsch. B,40b, No. 10, 1229–1232 (1985).

    CAS  Google Scholar 

  38. J. R. Grunwell, C. F. Hoyong, and J. A. Rieck,Tetrahedron Lett., No. 26, 2421–2423 (1973).

    Google Scholar 

  39. J. Kuyper and K. Vrieze,J. Organomet. Chem.,74, No. 2, 289–305 (1974).

    Article  CAS  Google Scholar 

  40. J. Kuyper and K. Vrieze,ibid.,86, No. 1, 127–138 (1975).

    CAS  Google Scholar 

  41. W. Sicinska, L. Stefaniak, M. Witanowski, and G. A. Webb,J. Mol. Struct.,158, No. 1, 57–68 (1987).

    Article  CAS  Google Scholar 

  42. S. C. Zimmerman,Bioorg. Chem. Front,2, No. 1, 33–71 (1991).

    CAS  Google Scholar 

  43. T. Chivers, X. Gao, and M. Parvez,J. Am. Chem. Soc.,117, No. 8, 2359–2360 (1995).

    Article  CAS  Google Scholar 

  44. T. Chivers, X. Gao, and M. Parvez,Inorg. Chem.,35, No. 1, 9–15 (1996).

    Article  CAS  Google Scholar 

  45. J. J. Mayerle, J. Kuyper, and J. B. Street,ibid.,17, No. 9, 2610–2613 (1978).

    CAS  Google Scholar 

  46. A. J. Banister, I. A. Gorrel, and R. S. Roberts,J. Chem. Soc., Faraday Trans. II,81, No. 12, 1783–1794 (1985).

    Article  CAS  Google Scholar 

  47. A. J. Banister, J. A. Durrant, I. A. Gorrel, and R. S. Roberts,ibid.,81, No. 5, 1771–1782 (1985).

    CAS  Google Scholar 

  48. A. V. Zibarev and I. V. Beregovaya,Rev. Heteroatom. Chem.,7, 171–190 (1992).

    CAS  Google Scholar 

  49. V. Luzzati,Acta Crystallogr.,4, 193–200 (1951).

    Article  CAS  Google Scholar 

  50. N. M. D. Brown, D. G. Lister, and J. K. Tyler,Spectrochim. Acta, A,26, No. 11, 2133–2138 (1970).

    Google Scholar 

  51. M.-T. Averbuch-Pouchot, A. Durif, A. J. Banister, et al.,J. Chem. Soc., Dalton Trans., 221–223 (1982).

  52. V. I. Ponomarev, O. S. Filipenko, and A. L. Atovmyan,Kristallografiya,21, No. 2, 392–394 (1976).

    CAS  Google Scholar 

  53. L. M. Weinstock and I. Shinkai,Comprehensive Heterocyclic Chemistry, Vol. 6, A. R. Katritzky and C. W. Rees (eds.), Pergamon, Oxford (1984), pp. 513–543.

    Google Scholar 

  54. A. Gieren, V. Lamm, R. C. Haddon, and M. L. Kaplan,J. Am. Chem. Soc.,101, No. 24, 7277–7281 (1979).

    Article  CAS  Google Scholar 

  55. A. Gieren, V. Lamm, R. C. Haddon, and M. L. Kaplan,ibid.,102, No. 15, 5070–5073 (1980).

    CAS  Google Scholar 

  56. Y. Tsubata, T. Suzuki, Y. Yamashita, et al.,Heterocycles,33, No. 1, 337–338 (1992).

    CAS  Google Scholar 

  57. K. Ono, S. Tanaka, and Y. Yamashita,Angew. Chem. Int.,33, No. 19, 1977–1979 (1994).

    Article  Google Scholar 

  58. I. Yu. Bagryanskaya, Yu. V. Gatilov, A. O. Miller, et al.,Heteroatom. Chem.,5, Nos. 5/6, 561–565 (1994).

    Article  CAS  Google Scholar 

  59. A. W. Cordes, M. Hojo, H. Koenig, M. C. Noble, et al.,Inorg. Chem.,25, No. 8, 1137–1145 (1986).

    Article  CAS  Google Scholar 

  60. A. V. Zibarev, Yu. V. Gatilov, and A. O. Miller,Polyhedron,11, No. 9, 1137–1141 (1992).

    Article  CAS  Google Scholar 

  61. R. Jones, J. L. Morris, A. W. Potts, et al.,J. Chem. Soc., Chem. Commun., 398–400 (1985).

  62. A. Gieren and F. Pertlick,Angew. Chem.,88, 852–853 (1976).

    Article  CAS  Google Scholar 

  63. I. Yu. Bagryanskaya, H. Bock, Yu. V. Gatilov, et al.,Chem. Ber., Recueil,130, No. 2, 247–253 (1997).

    Article  CAS  Google Scholar 

  64. A. C. Gomes, G. Biswas, A. Banerjee, and W. L. Duax,Acta Crystallogr. C,45, No. 1, 73–75 (1989).

    Article  Google Scholar 

  65. V. Bertini, P. Dapporto, F. Lucchesini, et al.,ibid.,40, 653–655 (1984).

    Google Scholar 

  66. R. Neidlein, D. Knecht, A. Gieren, and C. Ruiz-Perez,Z Naturforsch. B,42b, No. 1, 84–90 (1987).

    Google Scholar 

  67. A. V. Zibarev, I. Yu. Bagryanskaya, Yu. V. Gatilov, et al.,Khim. Geterotsikl. Soedin., No. 12, 1683–1688 (1990).

    Google Scholar 

  68. E. G. Awere, N. Burford, R. C. Haddon, et al.,Inorg. Chem.,29, No. 23, 4821–4830 (1990).

    Article  CAS  Google Scholar 

  69. J. W. Bats, H. Fuess, K. L. Weber, and H. W. Roesky,Chem. Ber.,116, No. 5, 1751–1755 (1983).

    Article  CAS  Google Scholar 

  70. N. Burford, B. W. Royan, A. Linden, and T. S. Cameron,Inorg. Chem.,28, No. 1, 144–150 (1989).

    Article  CAS  Google Scholar 

  71. F. H. Allen, O. Kennard, D. G. Watson, et al.,J. Chem. Soc., Perkin Trans. II, No. 12, S1-S19 (1987).

    Google Scholar 

  72. A. P. Hitchcock, R. S. De Witte, J. M. van Esbroek, et al.,J. Electr. Spectrosc. Relat. Phenom.,57, 165–187 (1991).

    Article  CAS  Google Scholar 

  73. N. E. Petrachenko, Yu. V. Gatilov, and A. V. Zibarev,ibid.,67, 489–492 (1994).

    CAS  Google Scholar 

  74. M. M. Shakirov, I. V. Beregovaya, and A. V. Zibarev,Khim. Geterotsikl. Soedin., No. 2, 262–265 (1995).

  75. J. L. Morris, C. W. Rees, and D. J. Rigg,J. Chem. Soc., Chem. Commun., No. 7, 396–397 (1985).

  76. R. C. Haddon, M. L. Kaplan, and J. H. Marshall,J. Am. Chem. Soc.,100, No. 4, 1235–1239 (1978).

    Article  CAS  Google Scholar 

  77. M. L. Kaplan, R. C. Haddon, F. C. Schilling, et al.,ibid.,101, No. 12, 3306–3308 (1979).

    CAS  Google Scholar 

  78. A. V. Zibarev, O. M. Fugaeva, A. O. Miller, et al.,Khim. Geterotsikl Soedin., No. 8, 1124–1133 (1990).

  79. J. P. Boutique, J. Riga, J. J. Verbist, et al.,J. Am. Chem. Soc.,104, No. 10, 2691–2697 (1982).

    Article  CAS  Google Scholar 

  80. J. P. Boutique, G. Pfister-Guillouzo, J. Riga, et al.,J. Electron Spectrosc. Relat. Phenom.,34, 199–202 (1984).

    Article  CAS  Google Scholar 

  81. C. L. Khetrapal and A. V. Patankar,Mol. Cryst. Liq. Cryst.,15, 367–371 (1972).

    Article  CAS  Google Scholar 

  82. L. V. Vilkov, V. S. Matryukov, and N. I. Sedova,Determination of the Geomtrical Structure of Free Molecules [in Russian], Khimiya, Leningrad (1978), p. 180.

    Google Scholar 

  83. G. K. MacLean, J. Passmore, M. J. Schriver, et al.,J. Chem. Soct Chem. Commun., 807–808 (1983).

  84. A. Gieren, V. Lamm, R. C. Haddon, et al.,Z Naturforsch. B,39b, No. 7, 975–984 (1984).

    CAS  Google Scholar 

  85. T. Suzuki, C. Kabuto, Y. Yamashita, and T. Mikai,Chem. Lett., 1129–1132 (1987).

  86. T. Suzuki, C. Kabuto, Y. Yamashita, et al.,ibid., No. 11, 2285–2288 (1987).

  87. V. N. Kovtonuyk, A. Yu. Makarov, M. M. Shakirov, and A. V. Zibarev,J. Chem. Soc., Chem. Commun., No. 16, 1991–1992 (1996).

  88. A. V. Zibarev, and A. O. Miller,J. Fluor. Chem.,50, No. 3, 359–363 (1990).

    Article  CAS  Google Scholar 

  89. O. L. Stiefvater,Z Naturforsch. A,33a, No. 2, 153–155 (1978).

    CAS  Google Scholar 

  90. F. A. Momany and R. A. Bonham,J. Am. Chem. Soc.,86, No. 2, 162–164 (1964).

    Article  CAS  Google Scholar 

  91. M. Mellini and S. Merlino,Acta Crystallogr. B,32, No. 4, 1074–1078 (1976).

    Article  Google Scholar 

  92. J. P. Schafer and S. K. Arora,J. Chem. Soc., Chem. Commun., No. 24, 1623–1624 (1971).

  93. T. Clivers,Chem. Rev.,85, No. 5, 341–365 (1985).

    Article  Google Scholar 

  94. P. Klinzing, W. Willing, U. Mueller, and K. Dehnicke,Z Anorg. Allg. Chem.,529, 35–45 (1985).

    Article  CAS  Google Scholar 

  95. A. Haas and M. Pryka,Chem. Ber.,128, No. 1, 11–22 (1995).

    Article  CAS  Google Scholar 

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  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Russia

    I. Yu. Bagryanskaya, Yu. V. Gatilov & A. V. Zibarev

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  1. I. Yu. Bagryanskaya
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  2. Yu. V. Gatilov
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  3. A. V. Zibarev
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Translated fromZhurnal Strukturnoi Khimii, Vol. 38, No. 5, pp. 988–1006, September-October, 1997.

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Bagryanskaya, I.Y., Gatilov, Y.V. & Zibarev, A.V. Molecular structure of azachalcogenenes with aromatic substituents. J Struct Chem 38, 829–845 (1997). https://doi.org/10.1007/BF02763898

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