NMR study of conformational exchange and double-well proton potential in intramolecular hydrogen bonds in monoanions of succinic acid and derivatives

Journal of Physical Chemistry A

Volumn 115, Issue 35, 2011, Pages 9828-9836

  Guo, Jing ^a   Tolstoy, Peter M ^a,b   Koeppe, B ^a   Denisov, Gleb S ^b   Limbach, Hans Heinrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SUBSTITUTION; CARBON SKELETON; CARBOXYLIC GROUP; CONFORMATIONAL EXCHANGE; CONFORMATIONAL INTERCONVERSION; COUNTERIONS; DOUBLE-WELL POTENTIAL; INTERCONVERSIONS; INTRAMOLECULAR HYDROGEN BOND; METHYL GROUP; MONOANIONS; NMR STUDIES; PROTON POTENTIALS; STERIC REPULSIONS; SUCCINIC ACIDS; TETRAALKYLAMMONIUM;

CHLORINE; CONFORMATIONS; ENERGY BARRIERS; FUNCTIONAL GROUPS; HYDROGEN; HYDROGEN BONDS; ISOMERS;

PROTONS;

EID: 80052304945     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp201073j     Document Type: Article

References (43)

1. Perrin, C. L.; Nielson, J. B. J. Am. Chem. Soc. 1997, 119, 12734-12741
2. Perrin, C. L. Acc. Chem. Res. 2010, 43, 1550-1557
3. Drobez, S.; Golic, L.; Leban, I. Acta Crystallogr. 1985, C41, 1503-1505
4. Madsen, D.; Flensburg, C.; Larsen, S. J. Phys. Chem. A 1998, 102, 2177-2188
5. Harte, S. M.; Parkin, A.; Goeta, A.; Wilson, C. C. J. Mol. Struct. 2005, 741, 93-96
6. Langkilde, A.; Madsen, D.; Larsen, S. Acta Crystallogr. 2004, B60, 502-511
7. Fillaux, F.; Leygue, N.; Tomkinson, J.; Cousson, A.; Paulus, W. Chem. Phys. 1999, 244, 387-403
8. Perrin, C. L. Science 1994, 266, 1665-1668
9. Perrin, C. L.; Lau, J. S. J. Am. Chem. Soc. 2006, 128, 11820-11824
10. Kidric, J.; Mavri, J.; Podobnik, M.; Hadzi, D. J. Mol. Struct. 1990, 237, 265-271
11. Schah-Mohammedi, P.; Shenderovich, I. G.; Detering, C.; Limbach, H.-H; Tolstoy, P. M.; Smirnov, S. N.; Denisov, G. S.; Golubev, N. S. J. Am. Chem. Soc. 2000, 122, 12878-12879
12. Steiner, Th.; Saenger, W. Acta Crystallogr. 1994, B50, 348-357
13. Steiner, Th. J. Chem. Soc., Chem. Commun. 1995, 1331-1332
14. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909-915
15. Steiner, Th. J. Phys. Chem. A 1998, 102, 7041-7052
16. Kashino, S.; Taka, J.; Yoshida, T.; Kubozono, Y.; Ishida, H.; Maeda, H. Acta Crystallogr. 1998, B54, 889-894
17. Kalsbeek, N. Acta Crystallogr. 1991, C47, 1649-1653
18. Schouwstra, Y. Acta Crystallogr. 1972, B28, 2217-2221
19. Price, D. J.; Roberts, J. D.; Jorgensen, W. L. J. Am. Chem. Soc. 1998, 120, 9672-9679
20. Rudner, M. S.; Jeremic, S.; Petterson, K. A.; Kent, D. R.; Brown, K. A.; Drake, M. D.; Goddard, W. A.; Roberts, J. D. J. Phys. Chem. A 2005, 109, 9076-9082
21. Smith, A. A.; Drake, M. D.; Rahim, A. K.; Roberts, J. D. J. Phys. Chem. A 2008, 112, 12367-12371
22. Retey, J.; Hull, W. E.; Snatzke, F.; Snatzke, G.; Wagner, U. Tetrahedron 1979, 35, 1845-1849
23. Cassidy, C. S.; Lin, J.; Tobin, J. B.; Frey, P. A. Bioorg. Chem. 1998, 26, 213-219
24. Perrin, C. L.; Thoburn, J. D. J. Am. Chem. Soc. 1992, 114, 8559-8565
25. Roberts, J. D. Acc. Chem. Res. 2006, 39, 889-896
26. Smith, R.; Brereton, I. M.; Chai, R. Y.; Kent, S. B. H. Nat. Struct. Biol. 1996, 3, 946-950
27. Perrin, C. L.; Lau, J. S.; Kim, Y.-J.; Karri, P.; Moore, C.; Rheingold, A. L. J. Am. Chem. Soc. 2009, 131, 13548
28. Tolstoy, P. M.; Schah-Mohammedi, P.; Smirnov, S. N.; Golubev, N. S.; Denisov, G. S.; Limbach, H.-H. J. Am. Chem. Soc. 2004, 126, 5621-5634
29. Tolstoy, P. M.; Guo, J.; Koeppe, B.; Golubev, N. S.; Denisov, G. S.; Smirnov, S. N.; Limbach, H.-H. J. Phys. Chem. A 2010, 114, 10775-10782
30. Limbach, H.-H.; Tolstoy, P. M.; Pérez-Hernández, N.; Guo, J.; Shenderovich, I. G.; Denisov, G. S. Israel J. Chem. 2009, 49, 199-216
31. Siegel, J. S.; Anet, F. A. L. J. Org. Chem. 1988, 53, 2629-2630
32. 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 B.04: Gaussian, Inc.: Pittsburgh, PA, 2003.
33. The MEXICO Suite of Programs for NMR Chemical Exchange Lineshape Calculation, version 3.0. Available at http://www.chemistry.mcmaster.ca/bain/ exchange.html. Accessed July 2011.
34. gNMR License Agreement. Available at http://home.cc.umanitoba.ca/ ~budzelaa/gNMR/gNMR-license.html.
35. Detering, C.; Tolstoy, P. M.; Golubev, N. S.; Denisov, G. S.; Limbach, H.-H. Dokl. Phys. Chem. 2001, 379, 1-4
36. Golubev, N. S.; Melikova, S. M.; Shchepkin, D. N.; Shenderovich, I. G.; Tolstoy, P. M.; Denisov, G. S. Z. Phys. Chem. 2003, 217, 1549-1563
37. Facelli, J. C.; Gu, Z.; McDermott, A. Mol. Phys. 1995, 86, 865-872
38. Guo, J.; Koeppe, B.; Tolstoy, P. M. Phys. Chem. Chem. Phys. 2011, 13, 2335
39. Chmielewski, P.; Ozeryanskii, V. A.; Sobczyk, L.; Pozharskii, A. F. J. Phys. Org. Chem. 2007, 20, 643-648
40. Golubev, N. S.; Detering, C.; Smirnov, S. N.; Shenderovich, I. G.; Denisov, G. S.; Limbach, H.-H.; Tolstoy, P. M. Phys. Chem. Chem. Phys. 2009, 11, 5154-5159
41. Ando, K. Phys. Rev. B 2005, 72, 172104
42. Garcia-Viloca, M.; Gonzalez-Lafont, A.; Lluch, J. M. J. Am. Chem. Soc. 1999, 121, 9198-9207
43. Steiner, T.; Majerz, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651-2654