Ab initio study of possible and preferred basic site(s) in polyfunctional N1,N1-dimethyl-N2-cyanoformamidine

Journal of Physical Chemistry A

Volumn 105, Issue 5, 2001, Pages 869-874

  Makowski, Mariusz ^a   Raczyńska, Ewa D ^b   Chmurzyński, Lech ^a  

^a UNIVERSITY OF GDA SK   (Poland)

^b WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; CHARGE TRANSFER; ELECTRON ENERGY LEVELS; HYDROGEN BONDS; MATHEMATICAL MODELS; MOLECULES; NITROGEN COMPOUNDS; PROTONS; REACTION KINETICS; WATER;

HYDROGEN BOND COMPLEX; POLYFUNCTIONAL DIMETHYL CYANOFORMAMIDINE; POLYFUNCTIONAL NITROGEN; PROTONATION;

POLYAMIDES;

EID: 0343338085     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp002458t     Document Type: Article

References (60)

1. Vaes, J.; Foubert, A. Z.; Zeegers-Huyskens, Th. Can. J. Chem. 1975, 53, 604.
2. Foubert, A.; Huyskens, P. L. Can. J. Chem. 1976, 54, 610.
3. Oszczapowicz, J.; Raczyńska, E. Pol. J. Chem. 1983, 57, 419.
4. Raczyńska, E. D.; Laurence, C.; Nicolet, P. J. Chem. Soc., Perkin Trans. 2 1988, 1491.
5. Raczyńska, E. D.; Laurence, C.; Berthelot, M. Can. J. Chem. 1992, 70, 2203.
6. Borgarello, M.; Houriet, R.; Raczyńska, E. D.; Drapala, T. J. Org. Chem. 1990, 55, 38.
7. Decouzon, M.; Gal, J.-F.; Maria, P.-C.; Raczyńska, E. D. J. Org. Chem. 1991, 56, 3669.
8. Raczyńska, E. D.; Maria, P.-C.; Gal, J.-F.; Decouzon, M. J. Org. Chem. 1992, 57, 5730.
9. Oszczapowicz, J. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, p 623, and references therein.
10. Raczyńska, E. D. Pol. J. Chem. 1998, 72, 1215, and references therein.
11. Häfelinger, G.; Kuske, F. K. H. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, p 1, and references therein.
12. Laurence, C.; Berthelot, M.; Raczyńska, E. D.; LeQuestel, J.-Y.; Duguay, G.; Hudhomme, P. J. Chem. Res. (S) 1990, 250.
13. Anulewicz, R.; Krygowski, T. M.; Raczyńska, E. D.; Laurence, C. J. Phys. Org. Chem. 1991, 4, 33.
14. Krygowski, T. M.; Anulewicz, R.; Raczyńska, E. D.; Laurence, C. J. Phys. Org. Chem. 1991, 4, 689.
15. Häfelinger, G.; Krygowski, T. M.; Kuske, F. K. H. Z. Naturforsch 1992, 47B, 1480.
16. Gal, J.-F.; Leito, I.; Maria, P.-C.; Raczyńska, E. D.; Taft, R. W.; Anvia, F. J. Chim. Phys. 1995, 92, 22.
17. Raczyńska, E. D.; Taft, R. W. Bull. Chem. Soc. Jpn. 1997, 70, 1297.
18. Raczyńska, E. D.; Decouzon, M.; Gal, J.-F.; Maria, P.-C.; Taft, R. W.; Anvia, F. J. Org. Chem. 2000, 65, 4635.
19. Raczyńska, E. D.; Mishima, M.; Mustanir, Bull. Chem. Soc. Jpn. 1998, 71, 2175.
20. Taft, R. W.; Raczyńska, E. D.; Maria, P.-C.; Leito, I.; Gal, J.-F.; Decouzon, M.; Drapala, T.; Anvia, F. Pol. J. Chem. 1995, 69, 41.
21. Maria, P.-C.; Leito, I.; Gal, J.-F.; Exner, O.; Decouzon, M. Bull. Soc. Chim. Fr. 1995, 132, 394.
22. Castano, O.; Notario, R.; Hori, K.; Abboud, J. L. M. Struct. Chem. 1996, 7, 321.
23. Raczyńska, E. D.; Maria, P.-C.; Gal, J.-F. Analyst 1998, 123, 621.
24. Hunter, E. P. I.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
25. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1990, 521.
26. Berthelot, M.; Helbert, M.; Laurence, C.; LeQuestel, J.-Y.; Anvia, F.; Taft, R. W. J. Chem. Soc., Perkin Trans. 2 1993, 625.
27. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
28. Makowski, M.; Liwo, A.; Wróbel, R.; Chmurzyński, L. J. Phys. Chem. A 1999, 103, 11104.
29. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
30. Möller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
31. Pople, J. A.; Brinkley, J. S.; Seeger, R. Int. Quantum. Chem. Symp. 1976, 10, 1.
32. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
35. Frish, C. P. M.; Trucks, G.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Anders, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. GAUSSIAN 94, VERSION B.3; Gaussian Inc.: Pittsburgh, PA, 1995.
36. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351.
37. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
38. Miertuš, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
39. Szafran, M.; Karelson, M. M.; Katritzky, A. R.; Koput, J.; Zerner, M. C. J. Comput. Chem. 1993, 14, 371.
40. Cammi, R.; Tomasi, J. J. Comput. Chem. 1995, 16, 1449.
41. Pomelli, C. S.; Tomasi, J. J. Theor. Chem. Acc. 1997, 96, 39.
42. Boys, S. F.; Bemardi, F. Mol. Phys. 1970, 19, 553.
43. Chałasiński, G.; Kendall, R. A.; Simons, J. J. Chem. Phys. 1987, 87, 2965.
44. Hamza, A.; Vibók, A.; Halász, G. J.; Mayer, I. J. Mol. Struct. (THEOCHEM) 2000, 501-502, 427, and references therein.
45. Perrin, C. L. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, p 147, and references therein.
46. Naulet, N.; Filleux, M. L.; Martin, G. J. Org. Magn. Reson. 1975, 7, 326.
47. Oszczapowicz, J.; Krawczyk, W.; Osek, J.; Raczyńska, E. J. Chem. Res. (S) 1985, 384.
48. Oszczapowicz, J.; Raczyńska, E.; Osek, J. Magn. Reson. Chem. 1986, 24, 9.
49. Exner, O.; Buděšínský, M.; Hnyk, D.; Všetečka, V.; Raczyńska, E. D. J Mol. Struct. 1988, 178, 147.
50. Kosturkiewicz, Z.; Ciszak, E.; Tykarska, E. Acta Crystallogr. Sect. B: Struct. Sci. 1992, B48, 471.
51. Cellerin, C.; Abouelfida, A.; Pradere, J. P.; Proutiere, A.; Roze, J. C.; Bouzid, M.; Exner, O. J. Mol. Struct. 1992, 265, 215.
52. Krygowski, T. M. J. Chem. Inf. Comput. Sci. 1993, 33, 70, and references cited therein.
53. Wiberg, K Tetrahedron 1978, 24, 1083.
54. Berthelot, M.; Helbert, M.; Laurence, C.; LeQuestel, J.-Y. J. Phys. Org. Chem. 1993, 6, 302.
55. Hout, R. F.; Levi, B. A.; Hehre, W. J. J. Comput. Chem. 1982, 3, 234.
56. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502, and references therein.
57. Perrin, D. D. Dissociation Constants of Organic Bases in Aqueous Solution; Butterworth: London, 1965.
58. Raczyńska, E. D. J. Chem Res. (S) 1991, 90.
59. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, February 2000; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 20899 (http://webbook.nist.gov/chemistry/).
60. Raczyńska, E. D. J. Chem. Res. (S) 1997, 214.