Effects of substitution of OH group by F atom for conformational preferences of fluorine-substituted analogues of (R,R)-tartaric acid, its dimethyl diester, diamide, and N,N,N',N'-tetramethyl diamide. Ab initio conformational analysis

Journal of the American Chemical Society

Volumn 121, Issue 9, 1999, Pages 1912-1921

  Hoffmann, Marcin ^a   Rychlewski, Jacek ^a,b   Rychlewska, Urszula ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORM; FLUORINE; HYDROXYL GROUP; TARTARIC ACID; TARTARIC ACID DERIVATIVE; WATER;

ARTICLE; CONFORMATIONAL TRANSITION; FREQUENCY ANALYSIS; GAS; HYDROGEN BOND; SOLVATION;

EID: 0033541035     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982935+     Document Type: Article

References (86)

1. Chapeau, M. C.; Frey, P. A. J. Org. Chem. 1994, 59, 6994-6998.
2. Lampe, D.; Liu, C.; Mahon, M. F.; Potter, B. V. L. J. Chem. Soc., Perkin Trans. 1996, 1, 1717-1727.
3. Walsh, C. Tetrahedron 1982, 38, 871-909.
4. Prestwich, G. D. Pestic. Sci. 1986, 17, 430-440.
5. Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. Tetrahedron 1996, 52, 12613-12622.
6. Mann, J. Chem Soc. Rev. 1987, 16, 381-436.
7. Seebach, D. Angew Chem., Int. Ed. Engl. 1990, 29, 1320-1367.
8. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
9. Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
10. McMurry, J. Fundamentals of Organic Chemistry; Wadsworth: Belmont CA, 1986.
11. Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195-285.
12. Bravo, P.; Resnati, G.; Angeli, P.; Frigerio, M.; Viani, F.; Amone, A. J. Med. Chem. 1992, 35, 3102-3110.
13. Filler, R., Kobayashi, Y., Eds. Biomedical aspects of fluorine chemistry; Kodansha: Tokyo (and Elsevier Biomedical Press: Amsterdam), 1982.
14. Kilbourn, M. R. Fluorine-18-Labeling of Radiopharmaceutical; National Academy Press: Washington, DC, 1990.
15. Liebman, J. F., Greenberg, A., Dolbier, W. R., Eds. Fluorine-containing molecules. Structure, reactivity, synthesis and applications; VCH Publishers: New York, 1988.
16. vib-rot, see: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
17. Szarecka, A.; Hoffmann, M.; Rychlewski, J.; Rychlewska, U. J. Mol. Struct. 1996, 374, 363-372.
18. Gawronski, J.; Gawronska, K.; Skowronek, P.; Rychlewska, U.; Warzajtis, B.; Rychlewski, J.; Hoffmann, M.; Szarecka, A. Tetrahedron 1997, 53, 6113-6144.
19. Rychlewska, U. Acta Crystallogr. 1992, C48, 965-969.
20. Szczepanska, B.; Rychlewska, U. In Correlations, Transformations and Interactions in Organic Chemistry; Jones, D. W., Katrusiak, A., Eds.; Oxford University Press: Oxford, 1994; pp 23-244.
21. Hoffmann, M.; Szarecka, A.; Rychlewski, J. Adv. Quantum Chem. 1998, 32, 109-125.
22. Rychlewska, U.; Warzajtis, B.; Hoffmann, M.; Rychlewski, J. Molecules 1997, 2, 106-113.
23. Polvarapu, P. L.; Ewing, C. S.; Chandramouly, T. J. Am. Chem. Soc. 1987, 109, 7382-7386.
24. Hoffmann, M.; Rychlewski, J.; Rychlewska, U. Comput. Methods Sci. Technol. 1996, 2, 51-63.
25. Despite (25,3S)-2,3-dideoxy-2,3-difluorotartaric acid (also known as (S,S)-2,3-difluorosuccinic acid) and (R,R)-tartaric acid having different absolute configurations, they belong to the same configurational series.
26. Pasteur, L. Ann. Chim. Phys. 1848, 24, 442.
27. Bijvoet, J. M.; Peerdman, A. F.; Van Bommel, A. J. Nature 1951, 168, 271-272.
28. Wilen, S. H. Top. Stereochem. 1971, 6, 107-176.
29. Wilen, S. H.; Collet, A.; Jacques, J. Tetrahedron 1977, 33, 2725-2736.
30. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981.
31. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
32. Roush, W. R.; Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979-3982.
33. Roush, W. R.; Grover, P. T. J. Org. Chem. 1995, 60, 3806-3813.
34. Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett 1991, 439-440.
35. Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041-1042.
36. Ishihara, K.; Gao, Q.; Yamamoto, H. J. Org. Chem. 1993, 58, 6917-6919.
37. Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979-988.
38. Haruta, R.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1982, 104, 7667-7669.
39. Toda, F.; Tanaka, K.; Nassimbeni, L.; Niven, M. Chem. Lett. 1988, 1371-1374.
40. Iribarren, I.; Aleman, C.; Bou, J. J.; Munoz-Guerra, S. Macromolecules 1996, 29, 4397-4405.
41. Iribarren, I.; Aleman, C.; Regano, C.; Martinez de Ilarduya, A.; Bou, J. J.; Munoz-Guerra, S. Macromolecules 1996, 29, 8413-8424.
42. For an explanation of graph set notation, see: (a) Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095-1096. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Etter M. C. Acc. Chem. Res. 1990, 23, 120-126. (d) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
43. For an explanation of graph set notation, see: (a) Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095-1096. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Etter M. C. Acc. Chem. Res. 1990, 23, 120-126. (d) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
44. For an explanation of graph set notation, see: (a) Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095-1096. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Etter M. C. Acc. Chem. Res. 1990, 23, 120-126. (d) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
45. For an explanation of graph set notation, see: (a) Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095-1096. (b) Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. 1990, B46, 256-262. (c) Etter M. C. Acc. Chem. Res. 1990, 23, 120-126. (d) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
46. Stern, F.; Beevers, C. A. Acta Crystallogr. 1950, 3, 341-346.
47. Okaya, Y.; Stemple, N. R.; Kay, M. I. Acta Crystallogr. 1966, 21, 237-243.
48. Albertson, J.; Oskarsson, A.; Stahl, K. J. Appl. Crystallogr. 1979, 12, 537-544.
49. Hargreaves, M. K.; Richardson, P. J. J. Chem. Soc. 1957, 2260-2271.
50. Barton, L. D.; Gargara, A. R.; Hecht, L.; Polavarapu, P. L.; Sugeta, H. Spectrochim. Acta 1992, 484, 1051-1066.
51. Ascenso, J.; Gil, V. M. S. Can. J. Chem. 1980, 58, 1376-1379.
52. Hasan, M. Org. Magn. Res. 1980, 14, 309-312.
53. Barron, L. D. Tetrahedron 1978, 34, 607-610.
54. Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1977, 99, 8061-8062.
55. Su, C. N.; Keiderling, T. A. J. Am. Chem. Soc. 1980, 102, 511-515.
56. Freedman, T. B.; Balukjian, G. A.; Nafie, L. A. J. Am. Chem. Soc. 1985, 107, 6213-6222.
57. Aleman, C.; Galembeck, S. E. J. Org. Chem. 1997, 62, 6562-6567.
58. Gawronski, J.; Gawronska, K.; Rychlewska, U. Tetrahedron Lett. 1989, 30, 6071-6074.
59. Nielsen, A. B.; Holder, A. J. GaussView User's reference: Gaussian Inc.: Pittsburgh, PA, 1997
60. The molecules studied are built from two identical halves, explains why the number of examined initial structures was 63 (i.e., 3(6 + 5 + 4 + 3 + 2 + 1)) instead of 108 (i.e., 3(6)(6)).
61. Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1994, 116, 3892-3900.
62. Hawkins, G. D.; Giesen, D. J.; Lynch, G. C.; Chambers, C. C.; Rossi, I.; Storer, J. W.; Li, J.; Rinaldi, T. Z. D.; Liotard, D. A.; Cramer, C. J.; Truhlar D. G. AMSOL version 6.5.3. Based in part on AMPAC, version 2.1 by Liotard, D. A.; Healy, E. F.; Ruiz, J. M.; Dewar M. J. S. and on EF by Jensen, F., University of Minnesota, 1998.
63. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
64. (b) Dewar, M. J. S.; Zoebisch, E. G. J. Mol. Struct. (THEOCHEM) 1988, 180, 1-21.
65. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264.
66. Chambers, C. C.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. 1996, 100, 16385-16398.
67. Giesen, D. J.; Gu, M. Z.; Cramer, C. J.; Truhlar, D. G. J. Org. Chem. 1996, 61, 8720-8721.
68. Giesen, D. J.; Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. Theor. Chem. Acc. 1997, 98, 85-109.
69. Chambers, C. C.; Giesen, D. J.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. 1997, 101, 2061-2069.
70. Frisch, M. A.; Trucks, G. W.; 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.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, 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.; Gonzalez, C.; Pople, J. A. Gaussian 94. Revision C.3; Gaussian Inc.: Pittsburgh, PA, 1995.
71. Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian Inc.: Pittsburgh, PA, 1996; pp 63-64.
72. Davidson, E. R.; Feller, D. Chem. Rev. 1986, 86, 681-696.
73. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
74. Pople, J. A.; Beveridge, D. L. Approximate Molecular Orbital Theory; McGraw-Hill: New York 1970.
75. Gronert, S.; O'Hair, R. A. J. J. Am. Chem. Soc. 1995, 117, 2071-2081.
76. Roelofsen, G.; Kanters, J. A.; Kroon, J.; Doesburg, H. M.; Koops, T. Acta Crystallogr. 1978, B34, 2565-2570.
77. Dunitz, J. D.; Taylor, R. Chem. Eur. J. 1997, 3, 89-98.
78. Jeffrey, G. A.; Ruble, J. R.; McMullan, R. K.; DeFrees, D. J.; Pople, J. A. Acta Crystallogr. 1981, B37, 1885-1890.
79. Moran, S.; Ren, R. X.-F.; Rumney, S., IV; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057.
80. Evans, T. A.; Seddon, K. R. Chem. Commun. 1997, 2023-2024.
81. Phelps, M. E.; Hoffman, E. J.; Sterlin, C.; Huang, S. C.; Robinson, G.; McDonald, N.; Schelbert, H.; Kuhl, D. E. J. Nucl. Med. 1978, 19, 1311-1319.
82. Mattos, C.; Rasmussen, B.; Ding, X.; Petsko, G. A.; Ringe, D. Nat. Struct. Biol. 1994, 1, 55-58.
83. Hughes, D. L.; Sieker, L. C.; Bieth, J.; Dimicoli, J. L. J. Mol. Biol. 1982, 162, 645-658.
84. Takahashi, L. H.; Radhakrishnan, R.; Rosenfield, R. E., Jr.; Meyer, E. F., Jr.; Trainor, D. A. J. Am. Chem. Soc. 1989, 111, 3368-3374.
85. Sierra, I. L.; Papamichael, E.; Sakarelos, C.; Dimicoli, J. L.; Prange, T. J. Mol. Recognit. 1990, 3, 36-44.
86. Pham, M.; Gdaniec, M.; Polonski, T. J. Org. Chem. 1998, 63, 3731-3734.