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X-ray crystallographic study of three (N→B)-borinates prepared from 8-hydroxyquinoline and 2-hydroxypyridine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

8-Hydroxyquinoline and 2-hydroxypyridine have been reacted with diphenylborinic acid or 9-BBN; the molecular structure of the resulting heterocycles has been studied by X-ray crystallography. A structural comparison of the so formed five- and six-membered heterocycles with similar complexes obtained from aliphatic amino alcohol and α-amino acid derivatives shows significant differences for the N→B, B−O and B−C bond lengths and some of the inner cycle bond angles. Other structural parameters discussed in this respect are the sum of bond lengths at the boron atom, the sum of bond angles in the heterocycle and the tetrahedral character of the boron atom. On the basis of these parameters a qualitative comparison of heterocycle stability is possible.

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References

  1. H. Höpfl, N. Farfan, D. Castillo R. Santillan, R. Contreras, F. J. Martķnez-Martķnez, M. Galvan, R. Alvarez, L. Fernandez, S., Halut, and J.-C. Daran,J. Organomet. Chem.,544, 175 (1997).

    Article  Google Scholar 

  2. H. Höpfl, N. Farfan, D. Castillo, R. Santillan, A. Gutierrez, and J.-C. Daran,J. Organomet. Chem.,553, 221 (1998).

    Article  Google Scholar 

  3. N. Farfan, D. Castillo, P. Joseph-Nathan, R. Contreras, and L. v. Szentpaly,J. Chem. Soc., Perkin Trans II, 527 (1992).

    Google Scholar 

  4. N. Farfan and R. Contreras,J. Chem. Soc., Perkin Trans II., 1787 (1988).

    Google Scholar 

  5. H. Höpfl and N. Farfan,Can. J. Chem.,76, 1853 (1998).

    Article  Google Scholar 

  6. N. Farfan, D. Silva, and R. Santillan,Heteroatom Chem.,4, 533 (1993).

    Article  Google Scholar 

  7. J. Trujillo, H. Höpfl, D. Castillo, R. Santillan, and N. Farfan,J. Organomet. Chem.,571, 21 (1998).

    Article  Google Scholar 

  8. A. T. Balaban, I. Haiduc, H. Höpfl, N. Farfan, and R. Santillan,Main Group Met. Chem.,19, 385 (1996).

    Google Scholar 

  9. H. Höpfl, N. Perez-Hernandez, S. Rojas-Lķna, R. Santillan, and N. Farfan,Heteroatom Chem.,9, 359 (1998).

    Article  Google Scholar 

  10. H. Höpfl, M. Galvan, N. Farfan, and R. Santillan,J. Mol. Struct. (Theochem).,427, 1 (1998).

    Article  Google Scholar 

  11. H. Höpfl,J. Organomet. Chem., in press.

  12. H. C. Brown and A. K. Gupta,J. Organomet. Chem.,341, 73 (1998).

    Article  Google Scholar 

  13. C. J. Strang, E. Henson, Y. Okamoto, M. A. Paz, and P. M. Gallop,Anal. Biochem.,178, 276 (1989).

    Article  PubMed  Google Scholar 

  14. E. Vedejs, S. C. Fields, S. Lin, and M. R. Schrimpf,J. Org. Chem.,60, 3028 (1995).

    Article  Google Scholar 

  15. L. K. Mohler and A. W. Czarnik,J. Amer. Chem. Soc.,115, 7037 (1993).

    Article  Google Scholar 

  16. K. E. Claas and E. Hohaus,Fresenius Z. anal. Chem.,322, 343 (1985).

    Article  Google Scholar 

  17. E. Hohaus and K. Essendorf,Z. Naturforsch.,35B, 319 (1980).

    Google Scholar 

  18. E. Hohaus,Z. anorg. allg. Chem.,484, 41, (1982).

    Article  Google Scholar 

  19. R. Boese, R. Köster, and M. Yalpani,Chem. Ber.,118, 670 (1985).

    Google Scholar 

  20. H. Hartmann,J. prakt. Chem.,328, 755 (1986).

    Article  Google Scholar 

  21. A. M. Brouwer, N. A. C. Bakker, P. G. Wiernig, and J. W. Verhoeven,J. Chem. Soc., Chem. Comm., 1094 (1991).

  22. Y. L. Chow, C. I. Johansson, and Z.-L. Lin,J. Phys. Chem.,100, 13381 (1996).

    Article  Google Scholar 

  23. T. O. Harju,J. Mol. Struct. (Theochem).,360, 135 (1996).

    Article  Google Scholar 

  24. T. O. Harju, J. E. Korppi-Tommola, A. H. Huizer, and C. A. G. O. Varma,J. Phys. Chem.,100, 3592 (1996).

    Article  Google Scholar 

  25. J. M. Halm,Tappi.,60, 90 (1977).

    Google Scholar 

  26. Halm J. M., Pat. 2,749,768 Ger. Offen.;C. A.,89, 110833u (1978).

    Google Scholar 

  27. Halm J. M., U. S. Pat. US4,123,268;C. A.,90, 95445u (1979).

    Google Scholar 

  28. R. Quintero, N. Farfan, H. Höpfl, and R. Santillan, unpublished work.

  29. R. Neu,Z. anal. Chem.,142, 335 (1945).

    Article  Google Scholar 

  30. D. Thierig and F. Umland,Z. anal. Chem.,215, 24 (1966).

    Article  Google Scholar 

  31. E. Hohaus and F. Umland,Chem. Ber.,102, 4025 (1969).

    Google Scholar 

  32. E. Hohaus and W. Riepe,Z. Naturforsch.,28b, 440 (1973).

    Google Scholar 

  33. W. Kliegel and D. Nanninga,Chem. Ber.,116, 2616 (1983).

    Google Scholar 

  34. V. I. Grachek, G. R. Motolko, and S. F. Naumova,Vesti Akad. Navuk BSSR, Khim. Navuk., 52 (1990).

  35. P. J. Bailey, G. Cousins, G. A. Snow, and A. J. White,Antimicrobial Agents and Chemotherapy.,17, 549 (1980).

    PubMed  Google Scholar 

  36. Batel B. P., U. S. Pat. US5,348,948;C. A.,121, 295089b (1994).

    Google Scholar 

  37. C. P. Brock, personal communication.

  38. S. J. Rettig and J. Trotter,Can. J. Chem.,51, 1288 (1973).

    Google Scholar 

  39. S. J. Rettig and J. Trotter,Can. J. Chem.,54, 3130 (1976).

    Google Scholar 

  40. M. Yalpani, R. Köster, R. Boese and M. Sulkowski,Chem. Ber.,122, 9 (1989).

    Google Scholar 

  41. J. B. Hendrickson,J. Amer. Chem. Soc.,83, 4537 (1961).

    Article  Google Scholar 

  42. W. J. Adams, H. J. Geise and L. S. Bartell,J. Amer. Chem. Soc.,92, 5013 (1970).

    Article  Google Scholar 

  43. D. Cremer,Israel J. Chem.,23, 72 (1983).

    Google Scholar 

  44. K. B. Wiberg, R. F. W. Bader, and C. D. H. Lau,J. Amer. Chem. Soc.,109, 985 (1987).

    Article  Google Scholar 

  45. J. A. Boatz, M. S. Gordon, and R. L. Hilderbrandt,J. Amer. Chem. Soc.,110, 352 (1988).

    Article  Google Scholar 

  46. W. Kliegel, S. J. Rettig, and J. Trotter,Can. J. Chem.,66, 1091 (1988).

    Google Scholar 

  47. H. Höpfl, M. Sanchez, V. Barba, N. Farfan, S. Rojas, and R. Santillan,Inorg. Chem.,37, 1679 (1998).

    Article  Google Scholar 

  48. W. Kliegel, H.-W. Motzkus, D. Nanninga, S. J. Rettig, and J. Trotter,Can. J. Chem.,64, 507 (1986).

    Google Scholar 

  49. I. A. Teslya, Z. A. Starikova, V. K. Trunov, T. N. Kukina, V. A. Dorokhov, and B. M. Mikhailov,Izv. Akad. Nauk SSSR, Ser. Khim., 2730 (1981).

  50. S. J. Rettig and J. Trotter,Can. J. Chem.,61, 2334 (1983).

    Google Scholar 

  51. C. Orvig, S. J. Rettig, and J. Trotter,Can. J. Chem.,65, 590 (1987).

    Google Scholar 

  52. S. J. Rettig and J. Trotter,Can. J. Chem.,54, 1168 (1976).

    Google Scholar 

  53. A. Lang, H. Nöth, and M. Schmidt,Chem. Ber.,128, 751 (1995).

    Google Scholar 

  54. M. Yalpani, R. Köster, and R. Boese,Chem. Ber.,122, 19 (1989).

    Google Scholar 

  55. G. E. Herberich, A. Fischer, and D. Wiebelhaus,Organometallics.,15, 3106 (1996).

    Article  Google Scholar 

  56. H. Binder, W. Matheis, H.-J. Deiseroth, and H. Fu-Son,Z. Naturforsch.,38b, 554 (1983).

    Google Scholar 

  57. H. Binder, W. Matheis, G. Heckmann, H.-J. Deiseroth, and H. Fu-Son,Z. Naturforsch.,40b, 934 (1985).

    Google Scholar 

  58. G. N. Chremos, H. Weidmann, and H. K. Zimmerman,J. Org. Chem.,26, 1683 (1961).

    Article  Google Scholar 

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Authors
  1. Herbert Höpfl
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  2. Victor Barba
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  3. Gabriela Vargas
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  4. Norberto Farfan
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  5. Rosa Santillan
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  6. Dolores Castillo
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Additional information

Universidad Autónoma del Estado de Morelos, Centro de Investigaciones Quimicas, C. P. 62210 Cuernavacca, México; Departmento de Quimica, Centro de Investigación y de Estudios Avanzados del IPN, Apdo. C. P. 07000 México D. F., México Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1041–1057, August, 1999.

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Höpfl, H., Barba, V., Vargas, G. et al. X-ray crystallographic study of three (N→B)-borinates prepared from 8-hydroxyquinoline and 2-hydroxypyridine. Chem Heterocycl Compd 35, 912–927 (1999). https://doi.org/10.1007/BF02252159

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  • DOI: https://doi.org/10.1007/BF02252159

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