Bifurcated hydrogen-bonding effect on the shielding and coupling constants in trifluoroacetyl pyrroles as studied by 1H, 13C and 15N NMR spectroscopy and DFT calculations

Magnetic Resonance in Chemistry

Volumn 45, Issue 3, 2007, Pages 220-230

  Afonin, Andrei V ^a   Ushakov, Igor A ^a   Mikhaleva, Al'bina I ^a   Trofimov, Boris A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

13C; 15N; 1H; Bifurcated hydrogen bonds; DFT calculations; NMR; Pyrroles

Indexed keywords

HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYRIDINE; SHIELDING;

13C; 15N; 1H; BIFURCATED HYDROGEN BONDS; COUPLING CONSTANTS; DFT CALCULATION; INTRAMOLECULAR HYDROGEN BOND; PYRIDINE RINGS; PYRIDYL; PYRROLE;

DENSITY FUNCTIONAL THEORY;

EID: 33947145209     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.1949     Document Type: Article

References (61)

1. Afonin AV, Ushakov IA, Sobenina LN, Stepanova ZV, Petrova OV, Trofimov BA. Magn. Reson. Chem. 2006; 44: 59.
2. (a) King MM, Yeh HJ, Dudek GO. Org. Magn. Reson. 1976; 8: 208;
3. (b) Vizioli C, Ruiz de Azua MC, Giribet CG, Contreras RH, Turi L, Dannenberg JJ, Rae ID, Weingold JA, Malagoli M, Zanasi R, Lazzeretti P. J. Phys. Chem. 1994; 98: 8858;
4. (c) Contreras RH, Barone V, Facelli JC, Peralta JE. Annu. Rep. NMR Spectrosc. 2003; 51: 167.
5. (a) Dingley AJ, Masse JE, Peterson RD, Barfield M, Feigon J, Grzesik S. J. Am. Chem. Soc. 1999; 121: 6019;
6. (b)Janke EMB, Dunger A, Limbach H-H, Weisz K. Magn. Reson. Chem. 2001; 39: s 177;
7. (c) Shenderovich IG, Tolstoy PM, Golubev NS, Smirnov SN, Denisov GS, Limbach H-H. J. Am. Chem. Soc. 2003; 125: 11710;
8. (d) Tolstoy PM, Smirnov SN, Shenderovich IG, Golubev NS, Denisov GS, Limbach H-H. J. Mol. Struct. 2004; 700: 19.
9. (a) Afonin AV, Ushakov IA, Petrova OV, Sobenina LN, Mikhaleva AI, Voronov VK, Trofimov BA. Zh. Org. Khim. 2000; 36: 1074;
10. (b) Afonin AV, Kuznetsova SY, Ushakov IA, Voronov VK, Mikhaleva AI, Schmidt EY. Zh. Org. Khim. 2002; 38: 1712;
11. (c) Afonin AV, Ushakov IA, Simonenko DE, Schmidt EY, Zorina NV, Mikhaleva AI, Trofimov BA. Zh. Org. Khim. 2005; 41: 1547.
12. (a) Trofimov BA, Sigalov MV, Tandura SN, Kalabin GA, Mikhaleva AI, Korostova SE. Russ. Chem. Bull. 1979; 28: 1562;
13. (b) Hilton J, Sutcliffe LH. Prog. NMR Spectrosc. 1975; 10: 27;
14. (c) Contreras RH, Natiello MA, Scuseria GE. Magn. Reson. Rev. 1985; 9: 239.
15. (a)Natiello MA, Contreras RH. Chem. Phys. Lett. 1984; 104: 568;
16. (b) Rae ID, Staffa A, Diz AC, Giribet CG, Ruiz de Azua MC, Contreras RH. Aust. J. Chem. 1987; 40: 1923.
17. Taylor R, Kennard O. J. Am. Chem. Soc. 1982; 104: 5063.
18. (a) Hoffman RA. Mol. Phys. 1958; 1: 326;
19. (b) Dewar MJS, Dougherty RC. The PMO Theory of Organic Chemistry. Plenum Press: New York, 1975.
20. (a) Dannenberg JJ, Haskamp L, Masunov A. J. Phys. Chem. A 1999; 103: 7083;
21. (b) Masunov A, Dannenberg JJ, Contreras RH. J. Phys. Chem. 2001; 105: 4737.
22. (a) Kuhn LP, Kleinspehn GG. J. Org. Chem. 1963; 28: 1963;
23. (b) Dabrowska U, Urbanski T. Spectrochim. Acta 1965; 21: 1965;
24. (c) Bureiko SF, Golubev NS, Pihlaya K, Mattiney J. Zh. Struct. Khim. 1991; 32: 87;
25. (d) Vokin AI, Gavrilova GA, Shulunova AM, Krivoruchka IG, Axamentova TN, Turchaninov VK. Zh. Obshch. Khim. 2004; 74: 269;
26. (e) Afonin AV, Ushakov IA, Simonenko DE, Schmidt EY, Zorina NV, Mikhaleva AI, Trofimov BA. Zh. Org. Khim. 2005; 41: 1547.
27. (a) Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1977; 7: 117;
28. (b) Shenderovich IG, Burtsev AP, Denisov GS, Golubev NS, Limbach HH. Magn. Reson. Chem. 2001; 39: S91;
29. (c) Pietrzak M, Limbach HH, Perez-Toralba M, Sanz D, Claramunt M, Elguero J. Magn. Reson. Chem. 2001; 39: S100.
30. Rusakov YuYu, Krivdin LB, Schmidt EY, Mikhaleva AI, Trofimov BA. Magn. Reson. Chem. 2006; 44: 692.
31. Contreras RH, Peralta JE. Prog. Nucl Magn. Reson. Spectrosc. 2000; 37: 321.
32. Ramsey NF. Phys. Rev. 1953; 91: 303.
33. Contreras RH, Facelli JC. Annu. Rep. NMR Spectrosc. 1993; 27: 256.
34. (a)Schaefer T, Kunkel IP, Shurko RW, Bernard GM. Can. J. Chem. 1994; 72: 1722;
35. (b) Schaefer T, Hazendonk P, McKinnon DM. Can. J. Chem. 1994; 73: 1387;
36. (c) Marton J, Szabo Z, Csorvassy I, Simon C, Hosztafi S, Makleit S. Tetrahedron 1996; 52: 2449.
37. (a) Dingley AJ, Cordier F, Grzesiek S. Concepts Magn. Reson. 2001; 13: 103;
38. (b) Alkorta I, Elguero J. Int. J. Mol. Sci. 2003; 4: 64;
39. (c) Mollova ET, Pardi A. Curr. Opin. Struct. Biol. 2000; 10: 298;
40. (e) Wilkens SJ, Westler WM, Weinhold F, Markley JL. J. Am. Chem. Soc. 2002; 124: 1190.
41. Rae ID, Weigold JA, Contreras RH, Biekofsky RR. Magn. Reson. Chem. 1993; 31: 836.
42. Bodenhausen G, Ruben D. J. Chem. Phys. Lett. 1980; 69: 185.
43. Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093.
44. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Nasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Kiene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malik DK, Rabuk AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Cliffords, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 2003. Gaussian, Inc: Pittsburg, PA, 2003.
45. Becke AD. J. Chem. Phys. 1993; 98: 5648.
46. Lee C, Yang W, Parr RP. Phys. Rev. 1988; B 38: 785.
47. (a) Krishnan R, Binkley JS, Seeger S, Pople JA. J. Chem. Phys. 1980; 72: 650;
48. (b) Clark T, Chandrasekhar J, Spitznagel GW, von Schleyer PR. J. Comput. Chem. 1983; 42: 94.
49. Pulay P. Mol. Phys. 1969; 17: 197.
50. (a) Ditchfield R. Mol. Phys. 1974; 27: 789;
51. (b) Wolinski K, Hilton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251.
52. (a) Woon DE, Dunning TH. J. Chem. Phys. 1993; 98: 650;
53. (b) Kendall RA, Dunning TH, Harrison RJ. J. Chem. Phys. 1992; 96: 6796.
54. (a) Peralta JE, Barone V, Contreras RH, Zaccari DG, Snyder JP. J. Am. Chem. Soc. 2001; 123: 9162;
55. (b) Barone V, Peralta JE, Contreras RH, Snyder JP. J. Am. Chem. Soc. 2002; 106: 5607;
56. (c) Peralta JE, Scuseria GE, Cheeseman JR, Frish MJ. Chem. Phys. Lett. 2003; 375: 452.
57. (a) Trofimov BA, Korostova SE, Balabanova LN, Mikhaleva AI. Khim. Geterocycl. Soedin. 1978; 489;
58. (b) Trofimov BA, Korostova SE, Balabanova LN, Mikhaleva AI. Zh. Org. Khim. 1978; 14: 2182.
59. Korostova SE, Mikhaleva AI, Sobenina LN, Shevchenko SG, Sigalov MV, Karataeva IM, Trofimov BA. Khim. Geterocycl. Soedin. 1989; 48.
60. (a) Petrova OV, Mikhaleva AI, Sobenina LN, Schmidt EY, EI. Mendeleev Commun. 1997; 162;
61. (b) Petrova OV, Mikhaleva AI, Sobenina LN, Schmidt EY, Kositsina EI. Zh. Org. Khim. 1997; 33: 1078.