Skip to main content

Penta- and Polynitrogen Compounds

  • Chapter
N Nitrogen

Abstract

Neither the cyclic nor the acyclic isomers of N5H have been observed experimentally; only organic derivatives of cyclopentazadiene, c-N5H, are known, but their thermal stability is low. The acyclic isomers of N5H are supposed to consist of a double-bonded N2 unit with a hydrogen and an N3 substituent. Each of the (Z) and (E) isomers forms an s-cis or s-trans conformer depending on the spatial arrangement of the approximately linear N3 unit with respect to the N-N double bond. An ab initio SCF MO calculation at the STO-3G level showed that cyclopentazadiene is the most stable isomer of N5H, followed by the (E) s-trans isomer of acyclic N5H and the (Z) s-trans, the (E) s-cis, and the (Z) s-cis isomers. The decomposition to HN3 and N2 is exothermal for all isomers of N5H. A mutual conversion between the (Z) and (E) isomers is predicted not to occur [1].

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 429.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 549.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Sana, M.; Leroy, G.; Nguyen, M.-T.; Elguero, J. (Nouv. J. Chim. 3 [1979] 607/21).

    CAS  Google Scholar 

  2. Carrion, F. (unpublished, ref. 18 in: Dewar, M. J. S.; Pure Appl. Chem. 44 [1975] 767/82).

    Article  Google Scholar 

  3. Mó, O.; de Paz, J. L. G.; Yáñez, M. (J. Phys. Chem. 90 [1986] 5597/604).

    Article  Google Scholar 

  4. Ferris, K. F.; Bartlett, R. J. (J. Am. Chem. Soc. 114 [1992] 8302/3).

    Article  CAS  Google Scholar 

  5. Waite, J.; Papadopoulos, M. G. (J. Phys. Chem. 94 [1990] 1755/8).

    Article  CAS  Google Scholar 

  6. Katritzky, A. R.; Barczinsky, P. (J. Prakt. Chem. 332 [1990] 885/97).

    Article  Google Scholar 

  7. Janoschek, R. (Angew. Chem. 105 [1993] 242/4;

    Article  CAS  Google Scholar 

  8. Janoschek, R. Angew. Chem. Int. Ed. Engl. 32 [1993] 230).

    Article  Google Scholar 

  9. Catalán, J.; De Paz, J. L. G.; Yáñez, M.; Elguero, J. (Chem. Scr. 24 [1984] 84/91).

    Google Scholar 

  10. Catalán, J.; Sanchez-Cabezudo, M.; De Paz, J. L. G.; Elguero, J. (J. Mol. Struct. 166 [1988] 415/20 [THEOCHEM 43]).

    Article  Google Scholar 

  11. Alcami, M.; Mó, O.; Yáñez, M. (J. Phys. Chem. 93 [1989] 3929/36).

    Article  CAS  Google Scholar 

  12. Ugi, I. (in: Katritzky, A. R.; Rees, C. W.; Comprehensive Heterocyclic Chemistry, Vol. 5, Pergamon, Oxford 1984, pp. 839/45).

    Google Scholar 

  13. Ritchie, C. D.; Wright, D. J. (J. Am. Chem. Soc. 93 [1971] 2429/32).

    Article  CAS  Google Scholar 

  14. Wallis, J. D.; Dunitz, J. D. (J. Chem. Soc. Chem. Commun. 1983 910/1).

    Google Scholar 

  15. Müller, R.; Wallis, J. D.; v. Philipsborn, W. (Angew. Chem. 97 [1985] 515/7;

    Article  Google Scholar 

  16. Müller, R.; Wallis, J. D.; v. Philipsborn, W. Angew. Chem. Int. Ed. Engl. 24 [1985] 513).

    Article  Google Scholar 

  17. Witanowski, M.; Stefaniak, L.; Januszewski, H.; Bahadur, K.; Webb, G. A. (J. Cryst. Mol. Struct. 5 [1975] 137/40).

    Article  CAS  Google Scholar 

References

  1. Pannetier, G.; Margineanu, F.; Dereigne, A.; Bonnaire, R. (Bull. Soc. Chim. Fr. 1972 2617/22).

    Google Scholar 

  2. Müller, E. (Ger. 634688 [1936]; C.A. 1937 511; cited as ref. 22 in [1]).

    Google Scholar 

  3. Patil, K. C.; Soundararajan, R.; Verneker, V. R. P. (Proc. Indian Acad. Sci. A 87 [1978] 281/4).

    Google Scholar 

  4. Chiglien, G.; Etienne, J.; Jaulmes, S.; Laruelle, P. (Acta Crystallogr. B 30 [1974] 2229/33).

    Article  Google Scholar 

  5. Reimlinger, H. (Chem. Ind. [London] 1972 294/5).

    Google Scholar 

  6. Veith, M.; Schlemmer, G. (Z. Anorg. Allg. Chem. 494 [1982] 7/19).

    Article  CAS  Google Scholar 

  7. Wannagat, U.; Kohnen, H. (Angew. Chem. 69 [1957] 783).

    Google Scholar 

  8. Rausch, D. A. (U.S. 3288659 [1924/66]; C.A. 66 [1967] No. 30647).

    Google Scholar 

  9. Rausch, D. A. (U.S. 3309248 [1924/67]; C.A. 67 [1967] No. 4515).

    Google Scholar 

  10. Paustian, J. E.; Fein, M. M. (U.S. 3459607 [1912/69] from C.A. 71 [1969] No. 83179).

    Google Scholar 

  11. Seamans, T. F.; Kahrs, J.; Huson, G. R. (J. Spacecr. Rockets 8 [1971] 1080/3).

    Article  CAS  Google Scholar 

  12. Burwell, W. G.; Oickle, C., Jr.; to United Aircraft Corp. (U.S. 3694770 [1972] 9 pp. from C.A. 77 [1972] No. 158689).

    Google Scholar 

  13. Ohtoshi, H.; Hanna, J.; Shimizu, I. (Eur. Appl. 228295 [1986/87] 39 pp. from C.A. 107 [1987] No. 145776).

    Google Scholar 

  14. Kanai, M.; Hanna, J.; Shimizu, I. (Ger. 3644652 [1986/87] 13 pp. from C.A. 108 [1988] No. 14906).

    Google Scholar 

  15. Kanai, M.; Hanna, J.; Shimizu, I. (Fr. 2592524 [1986/87] 25 pp. from C.A. 108 [1988] No. 86325).

    Google Scholar 

  16. Pannetier, G.; Margineanu, F.; Dereigne, A.; Bonnaire, R. (Bull. Soc. Chim. Fr. 1972 2623/5).

    Google Scholar 

  17. Patil, K. C.; Soundararajan, R.; Verneker, V. R. P. (Thermochim. Acta 31 [1979] 259/61).

    Article  CAS  Google Scholar 

  18. Rubtsov, Y. I.; Manelis, G. B. (Izv. Akad. Nauk SSSR Ser. Khim. 1984 296/9; Bull. Acad. Sci. USSR Div. Chem. Sci. [Engl. Transl.] 33 [1984] 260/3).

    Article  Google Scholar 

  19. Abello, L.; Margineanu, F. (C. R. Séances Acad. Sci. C 274 [1972] 916/8).

    CAS  Google Scholar 

  20. Axworthy, A. E.; Wagner, R. I. (AD-750900 [1972] 78 pp.; C.A. 78 [1973] No. 99926).

    Google Scholar 

  21. Kirpichev, E. P.; Alekseev, A. P.; Rubtsov, Y. I.; Manelis, G. B. (Zh. Fiz. Khim. 47 [1973] 2942;

    CAS  Google Scholar 

  22. Kirpichev, E. P.; Alekseev, A. P.; Rubtsov, Y. I.; Manelis, G. B. Russ. J. Phys. Chem. [Engl. Transl.] 47 [1973] 1654).

    Google Scholar 

  23. Brown, C. T.; McMahon, D. G.; Russell, S.; Fondrk, T.; Reed, I. (AD-745993 [1972] 187 pp.; C.A. 78 [1973] No. 74318).

    Google Scholar 

  24. Rubtsov, Y. I. (Gorenie Vzryv Mater. 3rd Vses. Simp., Leningrad 1971 [1972], pp. 771/4; C.A. 79 [1973] No. 35519).

    Google Scholar 

  25. Yakovleva, G. S.; Kurbangalina, R. K.; Stesik, L. N. (Fiz. Goreniya Vzryva 10 [1974] 270/4;

    CAS  Google Scholar 

  26. Yakovleva, G. S.; Kurbangalina, R. K.; Stesik, L. N. Combust. Explos. Shock Waves [Engl. Transl.] 10 [1974] 233/5).

    Article  Google Scholar 

  27. Apin, A. Ya.; Lebedev, Yu. A.; Nefedova, O. I. (Zh. Fiz. Khim. 32 [1958] 819/23).

    CAS  Google Scholar 

  28. Brown, C. T. (Propr. Hydrazine Ses Appl. Source Energ. Colloq. Int., Poitiers, Fr., 1974 [1975], pp. 245/65; C.A. 85 [1976] No. 110741).

    Google Scholar 

  29. Pannetier, G.; Margineanu, F. (Bull. Soc. Chim. Fr. 1972 3725/8).

    Google Scholar 

  30. Texaco Development Corp. (Fr. 2203940 [1972/74]; C.A. 82 [1975] No. 61422).

    Google Scholar 

References

  1. Wiberg, N.; Fischer, G.; Bachhuber, H. (unpublished, ref. 1 in: Wiberg, N.; Chimia 30 [1976] 426).

    Google Scholar 

  2. Kaim, W. (J. Chem. Soc. Perkin Trans. II 1985 1633/7).

    Google Scholar 

  3. Ferris, K. F.; Bartlett, R. J. (J. Am. Chem. Soc. 114 [1992] 8302/3).

    Article  CAS  Google Scholar 

Reference

  • Gal’pern, E. G.; Stankevich, I. V.; Chistyakov, A. L.; Shur, V. B.; Vol’pin, M. E. (Dokl. Akad. Nauk SSSR 302 [1988] 1384/8;

    Google Scholar 

  • Gal’pern, E. G.; Stankevich, I. V.; Chistyakov, A. L.; Shur, V. B.; Vol’pin, M. E. Dokl. Chem. [Engl. Transl.] 298/303 [1988] 302/5).

    Google Scholar 

References

  1. Van der Meer, K.; Mulder, J. J. C. (Theor. Chim. Acta 41 [1976] 183/6).

    Article  Google Scholar 

  2. BLahous, C. P.; Schaefer, H. F. (J. Mol. Struct. 200 [1989] 591/610 [THEOCHEM 59]).

    Article  Google Scholar 

References

  1. Leroy, G.; Sana, M.; Wilante, C.; Peeters, D.; Dogimont, C. (J. Mol. Struct. 153 [1987] 249/67 [THEOCHEM 38]).

    Article  Google Scholar 

  2. Sana, M.; Leroy, G. (Ann. Soc. Sci. Bruxelles I 101 [1988] 23/57).

    Google Scholar 

  3. Sana, M.; Leroy, G.; Vinson, L. K.; Dannenberg, J. J. (J. Mol. Struct. 205 [1990] 89/95 [THEOCHEM 64]).

    Article  Google Scholar 

Reference

  • Gal’pern, E. G.; Stankevich, I. V.; Chistyakov, A. L.; Shur, V. B.; Vol’pin, M. E. (Dokl. Akad. Nauk SSSR 302 [1988] 1384/8;

    Google Scholar 

  • Gal’pern, E. G.; Stankevich, I. V.; Chistyakov, A. L.; Shur, V. B.; Vol’pin, M. E. Dokl. Chem. [Engl. Transl.] 298/303 [1988] 302/5).

    Google Scholar 

Download references

Authors

Editor information

Dieter Koschel Peter Merlet Astrid Wietelmann Peter Merlet

Rights and permissions

Reprints and permissions

Copyright information

© 1993 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Haubold, R., Heinrich-Sterzel, C., Merlet, P., Ohms-Bredeman, U., Strametz, C., Wietelmann, A. (1993). Penta- and Polynitrogen Compounds. In: Koschel, D., Merlet, P., Wietelmann, A., Merlet, P. (eds) N Nitrogen. Gmelin Handbook of Inorganic and Organometallic Chemistry - 8th Edition, vol N / 0-b / b / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-06336-1_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-662-06336-1_4

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-06338-5

  • Online ISBN: 978-3-662-06336-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics