NMR studies and DFT calculations of the symmetric intramolecular NHN-hydrogen bond of bis-(2-pyridyl)-acetonitrile: Isotope labeling strategy for the indirect 13C-detection of 15N15N couplings

Journal of Molecular Structure

Volumn 844-845, Issue , 2007, Pages 222-231

  Pietrzak, Mariusz ^a,c   Benedict, Claudia ^a   Gehring, Holger ^b   Daltrozzo, Ewald ^b   Limbach, Hans Heinrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF KONSTANZ   (Germany)

^c INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

Author keywords

6 Aminofulvene 1 aldimines; 13C NMR; 15N NMR; 1H NMR; 1hJ(N,H); 2hJ(N,N); Hydrogen bond; NMR

Indexed keywords

CORRELATION METHODS; DISCRETE FOURIER TRANSFORMS; HEAVY IONS; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HEAVY ATOM DISTANCE; ISOTOPIC LABELING; MOLECULAR SYMMETRY; PROTON TAUTOMERISM;

ACETONITRILE;

EID: 35348921229     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2007.04.023     Document Type: Article

References (58)

1. Smirnov S.N., Golubev N.S., Denisov G.S., Benedict H., Schah-Mohammedi P., and Limbach H.H. J. Am. Chem. Soc. 118 (1996) 4094-4101
2. Limbach H.H., Pietrzak M., Sharif S., Tolstoy P.M., Shenderovich I.G., Smirnov S.N., Golubev N.S., and Denisov G.S. Chem. Eur. J. 10 (2004) 5195-5204
3. Shenderovich I.G., Smirnov S.N., Denisov G.S., Gindin V.A., Golubev N.S., Dunger A., Reibke R., Kirpekar S., Malkina O.L., and Limbach H.H. Ber. Bunsenges. Phys. Chem. 102 (1998) 422-428
4. Dingley A.J., and Grzesiek S. J. Am. Chem. Soc. 120 (1998) 8293-8297
5. Grzesiek S., Cordier F., Jaravine V., and Barfield M. Prog. Nucl. Magn. Reson. Spectrosc. 45 (2004) 275-300
6. Shenderovich I.G., Burtsev A.P., Denisov G.S., Golubev N.S., and Limbach H.H. Magn. Res. Chem. 39 (2001) S91-S99
7. Del Bene J.E., and Elguero J. J. Phys. Chem. 110 (2006) 7496-7502
8. Benedict H., Shenderovich I.G., Malkina O.L., Malkin V.G., Denisov G.S., Golubev N.S., and Limbach H.H. J. Am. Chem. Soc. 122 (2000) 1979-1988
9. Pietrzak M., Limbach H.H., Pérez-Torralba M., Sanz D., Claramunt R.M., and Elguero J. Magn. Reson. Chem. 39 (2001) S100-S108
10. Golubev N.S., Shenderovich I.G., Smirnov S.N., Denisov G.S., and Limbach H.H. Chem. Eur. J. 5 (1999) 492-497
11. Shenderovich I.G., Tolstoy P., Golubev N.S., Smirnov S.N., Denisov G.S., and Limbach H.H. J. Am. Chem. Soc. 125 (2003) 11710-11720
12. Dingley A.J., Masse J.E., Peterson R.D., Barfield M., Feigon J., and Grzesiek S. J. Am. Chem. Soc. 121 (1999) 6019-6027
13. Cordier F., and Grzesiek S. J. Am. Chem. Soc. 121 (1999) 1601-1602
14. Cordier F., Rogowski M., Grzesiek S., and Bax A. J. Magn. Reson. 140 (1999) 510-512
15. Pervushin K., Ono A., Fernandez C., Szyperski T., Kainosho M., and Wüthrich K. Proc. Natl. Acad. Sci. USA 95 (1998) 14147-14151
16. Cornilescu G., Ramirez B.E., Frank M.K., Clore G.M., Gronenborn A.M., and Bax A. J. Am. Chem. Soc. 121 (1999) 6275-6279
17. Cornilescu G., Hu J.S., and Bax A. J. Am. Chem. Soc. 121 (1999) 2949-2950
18. Scheurer C., and Brüschweiler R. J. Am. Chem. Soc. 121 (1999) 8661-8662
19. Pietrzak M., Wehling J., Limbach H.H., Golubev N.S., López C., Claramunt R.M., and Elguero J. J. Am. Chem. Soc. 123 (2001) 4338-4339
20. Ozeryanskii V.A., Pozharskii A.F., Bieńko A.J., Sawka-Dobrowolska W., and Sobczyk L. J. Phys. Chem. A 109 (2005) 1637-1642 (and references cited therein)
21. Berger S. J. Magn. Reson. 66 (1986) 555-557
22. Lloyd-Jones G.C., Harvey J.N., Hodgson P., Murray M., and Woodward R.L. Chem. Eur. J. 9 (2003) 4523-4535
23. Sperber N., Papa D., Schwenk E., Sherlock M., and Bloomfield N.J. J. Am. Chem. Soc. 73 (1951) 3856-3858
24. Griebel R. Ber. Bunsenges. Phys. Chem. 84 (1980) 84-91
25. Griebel R. Ber. Bunsenges. Phys. Chem. 84 (1980) 919-925
26. Scheibe G.E., Daltrozzo E., and Wörz O. Z. Physik. Chem. 64 (1969) 97-114
27. Fritsky I.O., Ott R., and Kramer R. Angew. Chem. Int. Ed. Engl. 39 (2000) 3255-3258
28. E. Daltrozzo, Habilitationsschrift, TU München, 1971.
29. E. Daltrozzo, Proc. XX. Coll. Spectr. Internat., Invited Lectures II, Prag, 1977, pp. 151-174.
30. Newkome G.R., Joo Y.J., Evans D.W., Pappalardo S., and Fronczek F.R. J. Org. Chem. 53 (1988) 786-790
31. Newkome G.R., Joo Y.J., Theriot K.J., and Fronczek F.R. J. Am. Chem. Soc. 108 (1986) 6074-6075
32. Mueller-Westerhoff U. J. Am. Chem. Soc. 92 (1970) 4849-4855
33. Ammon H.L., and Mueller-Westerhoff U. Tetrahedron 30 (1974) 1437-1443
34. Trueblood K.N. In: Domenicano A., and Hargittai I. (Eds). "Accurate Molecular Structures, Their Determination and Importance" (1992), Oxford University Press 200 (Chapter 8)
35. Barfield M., Dingley A.J., Feigon J., and Grzesiek S. J. Am. Chem. Soc. 123 (2001) 4014-4022
36. Grech E., Klimkiewicz J., Nowicka-Scheibe J., Pietrzak M., Schilf W., Pozharskii A.F., Ozeryanskii V.A., Bolvig S., Abildgaard J., and Hansen P.E. J. Mol. Struct. 615 (2002) 121-140
37. Stetten M.R., and Schoenheimer R. J. Biol. Chem. 153 (1944) 113-132
38. Pechmann H. Ann. Chem. 261 (1891) 151-172
39. Pechmann H., and Welsh W. Ber. Chem. Ges. 17 (1884) 2384-2390
40. Pechmann H., and Baltzer O. Ber. Chem. Ges. 24 (1891) 3144-3153
41. Coburn R.A., and Dudek G.O. J. Phys. Chem. 72 (1968) 1177-1181
42. F.M. Saidova, G.P. Gorbunova, USSR Fiz. khim. Issled. Sintetich. i Prirod. Soedin., Samarkand, 1980, pp. 68-74 (From Ref. Zh. Khim., 1981, Abstr. No. 11Zh204.).
43. Borror A.L., and Haeberer A.F. J. Org. Chem. 30 (1965) 243-246
44. W. Sulger, Ph. D. Thesis, University of Konstanz, 1981 (For carrying-out these very syntheses of bis-(2-pyridyl)-acetonitriles, we are much obliged to M. Neureiter.).
45. H. Gehring, Master Thesis, University of Konstanz, 1995.
46. H. Gehring, Ph.D. Thesis, University of Konstanz, ISBN 3-930803-47-X, 1998.
47. Gehring H., and Daltrozzo E. Helv. Chim. Acta 81 (1998) 236-250
48. Klemm K., Schaefer H., and Daltrozzo E. Chem. Ber. 112 (1979) 484-495
49. 15N NMR Spectroscopy (1981), Springer-Verlag, Berlin, Heidelberg, New York (p. 224)
50. Dischler B. Angew. Chem. 78 (1966) 653-663
51. Emsley J.W., Feeney J., and Sutcliffe L.H. High Resolution Nuclear Magnetic Resonance Spectroscopy vol. 1 (1965), Pergamon Press, Oxford pp. 357-364
52. Novak A. Struct. Bonding (Berlin) 18 (1974) 177-216
53. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C, Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayalla, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T.M. Keith, A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A7, Gaussian Inc., Pittsburgh, PA, 1998.
54. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford University Press, New York
55. March N.H. Electron Density Theory of Atoms and Molecules (1992), Academic Press, San Diego, CA
56. Steiner T. J. Phys. Chem. A 102 (1998) 7041-7052
57. Limbach H.H., Pietrzak M., Benedict H., Tolstoy P.M., Golubev N.S., and Denisov G.S. J. Mol. Struct. 706 (2004) 115-119
58. Limbach H.H., Denisov G.S., and Golubev N.S. In: Kohen A., and Limbach H.H. (Eds). Isotope Effects in the Biological and Chemical Sciences (2006), Taylor & Francis, Boca Raton, FL 193-230 (Chapter 7, Hydrogen Bond Isotope Effects Studied by NMR)