Solvent Effects on the Conformer Distribution of 2-Methoxypropanal and Chloroacetaldehyde. A Model Case for the Conformational Analysis in Solution of Chiral Aldehydes Including Polar Groups

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6485-6492

  Lecea, Begoña ^a   Arrieta, Ana ^a   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961983577     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970468t     Document Type: Article

References (91)

1. See, for example: (a) Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996. (b) Koskinen, A. Asymmetric Synthesis of Natural Products; Wiley: Chichester, 1993. (c) Nógrádi, M. Stereoselective Synthesis; VCH Publishers: Wenheim, 1987.
2. See, for example: (a) Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996. (b) Koskinen, A. Asymmetric Synthesis of Natural Products; Wiley: Chichester, 1993. (c) Nógrádi, M. Stereoselective Synthesis; VCH Publishers: Wenheim, 1987.
3. See, for example: (a) Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996. (b) Koskinen, A. Asymmetric Synthesis of Natural Products; Wiley: Chichester, 1993. (c) Nógrádi, M. Stereoselective Synthesis; VCH Publishers: Wenheim, 1987.
4. (a) Huryn, D. M. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: Oxford, 1991; pp 49-75.
5. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; pp 123-193.
6. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
7. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 975-990.
8. (a) Kilb, R. W.; Lin, C. C.; Wilson, E. B., Jr. J. Chem. Phys. 1957, 26, 1695.
9. (b) Bartell, L. S.; Guillory, J. P.; Parks, A. T. J. Phys. Chem. 1965, 69, 3043.
10. (c) Ronn, A. M.; Woods, R. C. J. Chem. Phys. 1966, 45, 3831.
11. (d) Abe, M.; Kuchitsu, K.; Shimanouchi, T. J. Mol. Struct. 1969, 4, 245.
12. (e) Pickett, H. M.; Scroggin, D. G. J. Chem. Phys. 1974, 44, 3954.
13. (f) Dyngeseth, S.; Schei, H.; Hagen, K. J. Mol. Struct. 1983, 102, 45.
14. (g) Thomas, L. P.; True, N. S.; Bohn, R. K. J. Phys. Chem. 1980, 84, 1785.
15. (h) Durig, J. R.; Guirgis, G. A.; Little, T. S.; Stiefvater, O. L. J. Chem. Phys. 1989, 91, 738.
16. Sakurai, T.; Takeshita, K.; Fukushi, K.; Konaka, S. J. Phys. Chem. 1990, 94, 1793.
17. (j) Durig, J. R.; Kenton, R.; Phan, H. V.; Little, T. S. J. Mol. Struct. 1991, 247, 237.
18. (a) Wiberg, K. B.; Martin, E. J. Am. Chem. Soc. 1985, 107, 5035.
19. (b) Bowen, J. P.; Pathiaseril, A.; Profeta, S., Jr.; Allinger, N. L. J. Org. Chem. 1987, 52, 5162.
20. (c) Wiberg, K. B.; Murcko, M. A. J. Comput. Chem. 1988, 9, 488.
21. (d) Durig, J. R.; Phan, H. V.; Little, T. S.; Van der Veken, B. J. J. Mol. Struct. (THEOCHEM) 1989, 202, 143.
22. (e) Berry, R. J.; Waltmann, R. J. Pakansky, J.; Hagler, A. T. J. Phys. Chem. 1995, 99, 10511.
23. (f) Jonsdottir, S. O.; Rasmussen, K. New. J. Chem. 1995, 19, 1113.
24. (g) DeTar, D. F. J. Org. Chem. 1995, 60, 7125.
25. (h) Miyahara, I.; Inazu, T. J. Mol. Struct. (THEOCHEM) 1996, 364, 131.
26. (a) Kao, P. N.; Turner, P. H. J. Am. Chem. Soc. 1979, 101, 4497.
27. (b) Durig, J. R.; Badawi, H. M.; Little, T. S.; Guirguis, G. A.; Kalasinsky, V. F. J. Mol. Struct. 1984, 125, 211.
28. (c) Durig, J. R.; Little, T. S. Croat. Chem. Acta 1988, 61, 529.
29. (d) Durig, J. R.; Badawi, H. M. Chem. Phys. 1990, 148, 193.
30. (e) Chounan, Y.; Takayuki, E.; Yamamoto, Y. J. Am. Chem. Soc. 1995, 117, 3167.
31. (a) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 8991.
32. (b) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1993, 49, 3971.
33. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH Publishers: Weinheim, 1990; pp 110-120 and references therein.
34. Karabatsos, G. J.; Fenlio, D. J. J. Am. Chem. Soc. 1969, 91, 1124.
35. (a) Abraham, R. J.; Bretschneider, E. In Internal Rotation in Molecules; Orville-Thomas, W. J., Ed.; Wiley: New York, 1974; p 481.
36. (b) Abraham, R. J.; Chadwick, D. J.; Sancassan, F. Tetrahedron 1982, 38, 1485.
37. (a) Allinger, J.; Allinger, N. L. Tetrahedron 1958, 2, 64.
38. (b) Djerasi, C. Optical Rotatory Dispersion; McGraw-Hill: New York, 1960; pp 125-126.
39. Varnali, T.; Aviyente, V.; Terryn, B.; Ruiz-López, M. F. J. Mol. Struct. (THEOCHEM) 1993, 280, 169.
40. Gaussian 94, Revision B.2. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzeski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. DeFrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
41. Hehre, W. J.; Radom, L.; Schleyer, P.v.R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 65-88 and references therein.
42. (a) Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
43. (b) Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1.
44. (a) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules, Oxford: New York, 1989.
45. (b) Bartolotti, L. J.; Fluchick, K. In Reviews in Computational Chemistry, Vol. 7; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH Publishers: New York, 1996; pp 187-216.
46. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
47. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
48. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev B 1980, 37, 785.
49. (d) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
50. McIver, J. W.; Komornicki, A. K. J. Am. Chem. Soc. 1972, 94, 2625.
51. Pople, J. A.; Schleyer, B.; Krishnan, R.; DeFrees, D. J.; Binkley, J. S.; Frisch, H.; Whiteside, R.; Hout, R. F., Jr.; Hehre, W. J. Int. J. Quantum Chem. Symp. 1981, 15, 269.
52. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
53. Wiberg, K. B.; Rabien, P. R. J. Comput. Chem. 1993, 14, 1504.
54. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
55. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
56. (a) Parr, R. G.; Donelly, R. A.; Levy, M.; Palke, W. E. J. Chem. Phys. 1978, 68, 3801.
57. (b) Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512.
58. (c) Mulliken, R. S. J. Chem. Phys. 1934, 2, 782.
59. Parr, R. G.; Chattaraj, P. K. J. Am. Chem. Soc. 1991, 113, 1854.
60. Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017.
61. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
62. (b) Simkin, B. Ya.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Horwood: London, 1995; pp 78-101.
63. (c) Cramer, C. J.; Truhlar, D. G. In Reviews in Computational Chemistry, Vol. VI; Lipkwitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1995; pp 1-72.
64. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
65. (a) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 523.
66. (b) Wong, M. W.; Wiberg, K B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645.
67. Morao, I.; Lecea, B.; Arrieta, A.; Cossío, F. P. J. Am. Chem. Soc. 1997, 119, 816.
68. Rivail, J.-L.; Rinaldi, D.; Ruiz-Lopez, M. In Theoretical and Computational Models for Organic Chemistry; Formosinho, S. J., Csizmadia, I. G., Arnaut, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1991; Vol. 339, pp 79-42.
69. Rinaldi, D.; Pappalardo, R. R. Quantum Chemistry Program Exchange; Indiana University: Bloomington, IN, 1992; Program No. 622.
70. (a) Tomasi, J.; Bonaccorsi, R.; Camini, R.; Olivares del Valle, F. J. J. Mol. Struct (THEOCHEM) 1991, 234, 401.
71. (b) Miertus, S.; Scrocco, E. Tomasi, J. Chem. Phys. 1981, 55, 117.
72. (c) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239.
73. (d) Camini, R.; Tomasi, J. J. Comput. Chem. 1995, 16, 1449.
74. (a) Wiberg, K. B.; Castejon, H.; Keith, T. A. J. Comput. Chem. 1996, 17, 185.
75. (b) Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. J. Phys. Chem. 1995, 99, 9072.
76. (c) Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A. J. Am. Chem. Soc. 1995, 117, 4261.
77. CSD User Manuals; Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, U.K.
78. Klyne, W.; Prelog, V. Experientia 1960, 16, 521.
79. Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447.
80. See, for example: (a) Roa, G.; Ugalde, J. M.; Cossío, F. P. J. Phys. Chem. 1996, 100, 9619. (b) Sponer, J. Leszczynski, J.; Hobza, P. J. Phys. Chem. 1996, 100, 1965.
81. See, for example: (a) Roa, G.; Ugalde, J. M.; Cossío, F. P. J. Phys. Chem. 1996, 100, 9619. (b) Sponer, J. Leszczynski, J.; Hobza, P. J. Phys. Chem. 1996, 100, 1965.
82. c) criterion, see: (a) Lecea, B.; Morao, I.; Arrieta, A.; Cossío, F. P. Eur. J. Chem. 1997, 3, 20. (b) López, X.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc. 1996, 118, 2718.
83. c) criterion, see: (a) Lecea, B.; Morao, I.; Arrieta, A.; Cossío, F. P. Eur. J. Chem. 1997, 3, 20. (b) López, X.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc. 1996, 118, 2718.
84. (a) Wiberg, K. B.; Marquez, M.; Castejon, H. J. Org. Chem. 1994, 59, 6817.
85. (b) Shambayatti, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 283-324.
86. (a) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748.
87. (b) For a mechanistic study on the effective participation of chelated complexes in nucleophilic additions to the carbonyl group, see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1178.
88. For recent interesting studies on temperature and solvent effects on the nucleophilic additions to aldehydes and related compounds, see: (a) Cainelli, G.; Giacomi, D.; Perciaccante, F. Tetrahedron: Asymmetry 1994, 5, 1913. (b) Cainelli, G.; Giacomini, D.; Walzl, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2150. (c) Cainelli, G.; Giacomini, D.; Galletti, P.; Marini, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2849.
89. For recent interesting studies on temperature and solvent effects on the nucleophilic additions to aldehydes and related compounds, see: (a) Cainelli, G.; Giacomi, D.; Perciaccante, F. Tetrahedron: Asymmetry 1994, 5, 1913. (b) Cainelli, G.; Giacomini, D.; Walzl, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2150. (c) Cainelli, G.; Giacomini, D.; Galletti, P.; Marini, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2849.
90. For recent interesting studies on temperature and solvent effects on the nucleophilic additions to aldehydes and related compounds, see: (a) Cainelli, G.; Giacomi, D.; Perciaccante, F. Tetrahedron: Asymmetry 1994, 5, 1913. (b) Cainelli, G.; Giacomini, D.; Walzl, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2150. (c) Cainelli, G.; Giacomini, D.; Galletti, P.; Marini, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2849.
91. For a computational study on cyanide additions to monosubstituted acetaldehydes using the L1A1 model, see: Cieplak, A. S.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 9226.