Experimental and computational studies on aminoguanidine free base, monocation and dication, part II: Acid-base properties, gas phase protonation energies and total energies of two tautomers of the free base

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 52, Issue 10, 1997, Pages 1259-1272

  Koskinen, Jere T ^a   Koskinen, Mikko ^b   Mutikainen, Ilpo ^b   Tilus, Pirkko ^b   Mannfors, Berit ^a   Elo, Hannu ^c  

^a Department of Physics   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

^c Department of Pharmacy ^*  (Finland)

Author keywords

Acid Base Properties; Aminoguanidine; Resonance; Tautomerism

Indexed keywords

ALKALINITY; DENSITY FUNCTIONAL THEORY; IONS; PROTONATION; QUANTUM CHEMISTRY; RESONANCE;

ACID-BASE PROPERTY; AMINOGUANIDINE; COMPUTATIONAL STUDIES; DENSITY-FUNCTIONAL METHODS; ELECTROSTATIC REPULSION; GAS-PHASE PROTONATION; QUANTUM CHEMICAL CALCULATIONS; TAUTOMERISM;

GASES;

EID: 3042874215     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-1997-1018     Document Type: Article

References (48)

1. H. Elo, Bis(amidinohydrazones) ['bis(guanylhydrazones)'] as antineoplastic agents. Chemical and biochemical studies, Ph.D. Dissertation, University of Helsinki, Department of Biochemistry, Helsinki (1989), and references therein.
2. H. Elo, R. Laine, L. Alhonen-Hongisto, J. Jänne, I. Mutikainen, P. Lumme, Z. Naturforsch. 40c, 839 (1985).
3. H. Elo, I. Mutikainen, L. Alhonen-Hongisto, R. Laine, J. Jänne, P. Lumme, Z. Naturforsch. 41c, 851 (1986).
4. H. Elo, I. Mutikainen, L. Alhonen-Hongisto, R. Laine and J. Jänne, Cancer Lett. 41, 21 (1988).
5. H. Elo, I. Mutikainen, Z. Naturforsch. 43c, 601 (1988).
6. I. Mutikainen, H. Elo, P. Lumme, J. Chem. Soc., Perkin Trans. II, 1986, 291.
7. P. O. Lumme, I. Mutikainen, H. O. Elo, Acta Crystallogr. C42, 1209 (1986).
8. H. Elo, Spectrosc. Lett. 22, 123 (1989).
9. H. Elo, Spectrosc. Lett. 22, 161 (1989).
10. H. Elo, K. Soljamo, Spectrosc. Lett. 22, 1141 (1989).
11. H. O. Elo, P. T. E. Tilus, I. P. Mutikainen, I. Heikkinen, M.-L. Riekkola, Anti-Cancer Drug Design 4, 303 (1989).
12. H. Elo, Spectrosc. Lett. 23, 877 (1990).
13. H. Elo, Spectrosc. Lett. 25, 1267 (1992).
14. K. Soljamo, H. Elo, Spectrosc. Lett. 25, 1315 (1992).
15. M. Koskinen, H. Elo, Spectrosc. Lett. 27, 889 (1994).
16. M. Koskinen, J. Lummila, H. Elo, Spectrosc. Lett. 27, 1187 (1994).
17. M. Koskinen, I. Mutikainen, H. Elo, Z. Naturforsch. 49b, 556 (1994).
18. I. Mutikainen, M. Koskinen, H. Elo, Pharmazie 49, 739 (1994).
19. J. T. Koskinen, M. Koskinen, I. Mutikainen, B. Mannfors, H. Elo, Z. Naturforsch. 51b, 1771 (1996).
20. B. Mannfors, J. T. Koskinen, L.-O. Pietilä, L. Ahjopalo, J. Mol. Struct., Theochem, in press.
21. B. Mannfors, J. T. Koskinen, L.-O. Pietilä, J. Mol. Struct., in press.
22. L. Pauling, The Nature of the Chemical Bond, p. 268, Cornell University Press, Ithaca NY (1960).
23. W. J. Jones, Trans. Faraday Soc. 55, 524 (1959).
24. A. M. Sapse, G. Snyder, A. V. Santoro, Int. J. Quantum. Chem. 20, 755 (1981).
25. M. L. Williams, J. E. Gready, J. Comput. Chem. 10, 35 (1989).
26. P. Gund, J. Chem. Ed. 49, 100 (1972), and refs. cited therein.
27. K. B. Wiberg and R. Glaser, J. Am. Chem. Soc. 114, 841 (1992).
28. K. B. Wiberg, J. Am. Chem. Soc. 112, 4177 (1990).
29. P. Kollman, J. McKelvey, P. Gund, J. Am. Chem. Soc. 97, 1640 (1975).
30. J. Klein, A. Medlik, J. Chem. Soc. Commun. 275 (1973).
31. J. Klein, Tetrahedron 39, 2733 (1983).
32. I. Agranat, A. Skancke, J. Am. Chem. Soc. 107, 867 (1985).
33. F. G. Bordwell, G.-Z. Ji, J. Am. Chem. Soc. 113, 8398 (1991).
34. B. Amekraz, J. Tortajada, J.-P. Morizur, A. I. González, O. Mó, M. Yáñez, I. Leito, P.-C. Maria, J.-F. Gal, New J. Chem. 20, 1011 (1996).
35. A. Gobbi, G. Frenking, J. Am. Chem. Soc. 115, 2362 (1993).
36. Gaussian 94, Revision B.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA (1995).
37. C. M. Breneman, K. B. Wiberg, J. Comput. Chem. 11, 361 (1990).
38. R. Camitini, A. Pierretti, L. Bencivenni, F. Ramodo, N. Sanna, J. Phys. Chem. 100, 10928 (1996).
39. P. Kebarle, A. M. Hogg, J. Chem. Phys. 42, 798 (1965).
40. P. Kebarle, A. M. Hogg, J. Chem. Phys. 43, 449 (1965).
41. C. R. Moylan, J. J. Brauman, Ann. Rev. Phys. Chem. 34, 187 (1983).
42. M. J. Meot-Ner, J. Am Chem. Soc. 105, 4896 (1984).
43. M. Meot-ner (Mautner), in M. T. Bowers (ed.): Gas Phase Chemistry, Vol. 2, Academic Press, New York (1979).
44. R. G. Cooks, T. L. Kruger, J. Am. Chem. Soc. 99, 1279 (1977).
45. R. G. Cooks, J. S. Patrick, T. Kotiaho, S. A. McLuckey, Mass Spec. Rev. 13, 287 (1994).
46. J. B. Foresman and Æ. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian, Inc., Pittsburgh PA (1996).
47. A. I. Gonzalez, O. Mo, M. Yanez, E. Leon, J. Tortajada, J. P. Morizur, I. Leito, P. C. Maria, J. F. Gal, J. Phys. Chem. 100, 10490 (1996).
48. D. R. Herschbach, in A. Zewail (ed.): The Chemical Bond, Structure and Dynamics, pp. 175-222, Academic Press, San Diego (1992).