Study of the effect induced by the substituents on the ring-chain tautomerism of schiff bases derived from norephedrine

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3294-3300

  Talancón, Daniel ^a   Bosque, Ramon ^a   López, Concepción ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CLOSED FORM; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIASTEREOMERS; FERROCENYL; MOLAR RATIO; NMR STUDIES; OXAZOLIDINES; RING-CHAIN TAUTOMERISM; SCHIFF BASIS; SOLUTION BEHAVIOR; SPECTROSCOPIC PROPERTY; TAUTOMERIC EQUILIBRIA; TEMPERATURE DEPENDENT;

DENSITY FUNCTIONAL THEORY; FUNCTIONAL GROUPS; NITROGEN COMPOUNDS;

ORGANIC POLYMERS;

IMINE; NOREPHEDRINE; OXAZOLIDINE DERIVATIVE; SCHIFF BASE;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; TAUTOMERIC SHIFT; TEMPERATURE DEPENDENCE;

COMPUTER SIMULATION; MOLECULAR STRUCTURE; PHENYLPROPANOLAMINE; SCHIFF BASES; STEREOISOMERISM;

EID: 77952497781     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100255k     Document Type: Article

References (72)

1. Valters, R. E. and Flitsch, W. Ring-Chain Tautomerism; Plenum Press: New York, 1985.
2. Lázár, L.; Fülöp, F. Eur. J. Org. Chem. 2003, 3025-3042 and references cited therein
3. Szatmári, I.; Martinek, T. A.; Lázár, L.; Koch, A.; Kleinpeter, E.; Neuvonen, K.; Fülöp, F. J. Org. Chem. 2004, 69, 3645-3653
4. For recent contributions in this field: Keiko, N. A.; Vchislo, N. V.; Stepanova, L. G.; Larina, L. I.; Chuvashev, Y. A.; Funtikova, E. A. Chem. Heterocycl. Compd. 2008, 44, 1466-1471
5. Pihlaja, K.; Juhasz, M.; Kivelä, H.; Fülöp, F. Rapid. Commun. Mass Spectrosc. 2008, 22, 1510-1518
6. Juhasz, M.; Lázár, L.; Fülöp, F. J. Heterocycl. Chem. 2007, 44, 1465-1473
7. Peng, L.-J.; Liu, Z.-Q.; Wang, J.-T.; Wu, L.-M. Tetrahedron Lett. 2007, 48, 7418-7421
8. Selambarom, J.; Smadja, J.; Thomas, O.; Parrot, I.; Martínez, J.; Pavia, A. A. Int. J. Pept. Res. Ther. 2005, 11, 267-270
9. Strong, E. T. J.; Cardile, S. A.; Brazeau, A. L.; Jennings, M. C.; McDonald, R.; Jones, N. D. Inorg. Chem. 2008, 47, 10575-15086
10. Caputo, C. A.; Jones, N. D. Dalton Trans. 2007, 4627-4640
11. Cardile, S. A.; Jennings, M. C.; Jones, N. D. Dalton Trans. 2006, 4672-4678
12. Pérez, S.; López, C.; Caubet, A.; Roig, A.; Molins, E. J. Org. Chem. 2005, 70, 4857-4860
13. Krieg, R.; Wyrwa, R.; Möllmann, U.; Görls, H; Schönecker, B. Steroids 1998, 63, 531-541
14. Pérez, S.; López, C.; Caubet, A; Solans, X.; Font-Bardía, M.; Roig, A.; Molins, E. Organometallics 2006, 25, 596-601
15. López, C.; Caubet, A.; Pérez, S.; Solans, X.; Font-Bardía, M.; Roig, A.; Molins, E. Chem. Commun. 2004, 540-541
16. López, C.; Caubet, A.; Pérez, S.; Solans, X.; Font-Bardía, M. Eur. J. Inorg. Chem. 2006, 3974-3984
17. Benito, M.; López, C.; Solans, X.; Font-Bardía, M. Tetrahedron: Asymmetry 1998, 9, 4219-4238
18. Moyano, A.; Rosol, M.; Moreno, R. M.; López, C.; Maestro, M. A. Angew. Chem., Int. Ed. 2005, 44, 1865-1869
19. Platero, A. E.; Pérez, S.; López, C.; Solans, X.; Font-Bardía, M.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F.; Freixa, Z. J. Organomet. Chem. 2007, 692, 4215-4226
20. Moreno, R. M.; Catass, M.; López, C.; Moyano, A. Eur. J. Org. Chem. 2008, 2388-2396
21. Gibert, L.; González, A.; Granell, J.; López, C. Tetrahedron: Asymmetry 2002, 13, 983-988
22. López, C.; Caubet, A.; Bosque, R.; Solans, X.; Font-Bardía, M. J. Organomet. Chem. 2002, 645, 146-151
23. González, A.; Granell, J.; López, C. J. Organomet. Chem. 2001, 637-639, 116-125
24. Pou, D.; Platero, A. E.; Pérez, S.; López, C.; Solans, X.; Font-Bardía, M.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F.; Freixa, Z. J. Organomet. Chem. 2007, 692, 5017-5025
25. González, A.; López, C.; Solans, X.; Font-Bardía, M. J. Organomet. Chem. 2008, 693, 2877-2886
26. López, C.; Caubet, A.; Solans, X.; Font-Bardía, M. J. Organomet. Chem. 2000, 598, 87-102
27. López, C.; Sales, J.; Solans, X.; Zquiak, R. J. Chem. Soc., Dalton Trans. 1992, 2321-2328
28. Bosque, R.; López, C.; Sales, J.; Solans, X.; Font-Bardía, M. J. Chem. Soc., Dalton Trans. 1994, 735-745
29. López, C.; Bosque, R.; Solans, X.; Font-Bardía, M. New J. Chem. 1996, 20, 1285-1292
30. Hetényi, A.; Szakonyi, Z.; Klika, K. D.; Pihlaja, K.; Fülöp, F. J. Org. Chem. 2003, 68, 2175-2184
31. Star, A.; Fuchs, B. J. Org. Chem. 1999, 64, 1166-1172
32. Fülöp, F.; Pihlaja, K.; Neuvonen, K.; Bernáth, G.; Argay, G.; Kálmán, A. J. Org. Chem. 1993, 58, 1967-1969
33. Neuvonen, K.; Fülöp, F.; Neuvonen, H.; Koch, A.; Kleinpeter, E.; Pihlaja, K. J. Org. Chem. 2001, 66, 4132-4140
34. Lázár, L.; Lakatos, A. G.; Fülöp, F.; Bernáth, G.; Riddell, F. G. Tetrahedron 1997, 53, 1081-1088
35. Riddell, F. G.; Arumugan, S.; Fülöp, F.; Bernáth, G. Tetrahedron 1992, 48, 4979-4984
36. Fülöp, F.; Bernáth, G.; Mattinen, J.; Pihlaja, K. Tetrahedron 1989, 45, 4317-4325
37. Vainiotalo, P.; Ronkanen, S.; Fülöp, F.; Pihlaja, K. Tetrahedron 1990, 46, 3683-3692
38. Astudillo, M. E. A.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnell, P. D. Tetrahedron 1985, 41, 5919-5928
39. McDonagh, A. F.; Smith, H. E. J. Org. Chem. 1968, 33, 1-8
40. Fc = 5.40, 4.64, 4.44, and 4.02 for T = 298, 273, 253, and 233 K, respectively.
41. II was 1.57, 1.66, 1.75, and 1.82 for T = 298, 273, 253, and 233 K, respectively.
42. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736
43. 1H NMR spectrum of 2b at 298 K, thus suggesting that if present in solution their abundance should be extremely low.
44. II) = 51.
45. Brown, E. R.; Sandifer, J. R. In Physical Methods in Chemistry. Electrochemical Methods; Rossiter, B. W.; Hamilton, J. H., Eds.; Wiley: New York, 1986; Vol. 4, Chapter 4.
46. Bosque, R.; López, C.; Sales, J. Inorg. Chim. Acta 1996, 244, 141-145
47. Fülöp, F.; Bernáth, G.; Pihlaja, K. Adv. Heterocycl. Chem. 1997, 69, 349-477 and references cited therein
48. Valters, R. E.; Fülöp, F.; Korbonits, D. Adv. Heterocycl. Chem. 1996, 66, 1-403
49. Valters, R. E.; Fülöp, F.; Korbonits, D. Adv. Heterocycl. Chem. 1995, 64, 251-321
50. Hetényi, A.; Szakonyi, Z.; Klika, K. D.; Pihlaja, K.; Fülöp, F. J. Org. Chem. 2003, 68, 2175-2182
51. Szatmári, I.; Martinek, T. A.; Lázar, L.; Fülöp, F. Tetrahedron 2003, 59, 2877-2844
52. Allaway, C. L.; Daly, M.; Nieuwenhuyzen, M.; Saunders, G. C. J. Fluorine Chem. 2002, 115, 91-99
53. Szakonyi, Z.; Fülöp, F.; Bernáth, G.; Evanics, F.; Riddell, F. G. Tetrahedron 1998, 54, 1013-1020
54. Riddell, F. G.; Rogerson, M.; Fülöp, F.; Bernáth, G. Magn. Reson. Chem. 1995, 33, 600-603
55. Saeed, A. A. H. J. Heterocycl. Chem. 1982, 19, 113-115
56. McDonagh, A. F.; Smith, H. E. J. Chem. Soc., Chem. Commun. 1966, 374-375
57. 5-MeTf = 9.1 (at 233 K) and 16.7 (at 298 K), respectively.
58. II) were not detected.
59. 6).
60. 1 = Ph, under identical experimental conditions, we also studied the solution behavior of the imine (1 S,2 R)-[PhCH-NCH(Me) CH(OH)Ph] (2e).
61. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5692
62. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
64. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
65. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298
66. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310
67. For C, H, and N, the D95 basis set is used: Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F.., III, Ed.; Plenum Press: New York, 1976; Vol. 3, p 1.
68. 1 = Fc).
69. See, for instance: Hurtado, M.; Contreras, J. G.; Matamala, A.; Mó, O.; Yañez, M. New J. Chem. 2009, 32, 2209-2217
70. Riddell, F. G.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1977, 588-591
71. 1 is Fc.
72. For C, H, and N, the D95 basis set is used: Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum Press: New York, 1976; Vol. 3, p 1.