Relative energies, stereoelectronic interactions, and conformational interconversion in silacycloalkanes

International Journal of Quantum Chemistry

Volumn 100, Issue 5, 2004, Pages 720-732

  Freeman, Fillmore ^a   Fang, Christine ^a   Shainyan, Bagrat A ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

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

Author keywords

Conformational interconversion; Intrinsic reaction path (IRC) calculation; Stereodynamics; Transition state

Indexed keywords

CONFORMATIONAL INTERCONVERSION; INTRINSIC REACTION PATH (IRC) CALCULATION; STEREODYNAMICS; TRANSITION STATE;

CARBON; CHEMICAL BONDS; PARAMETER ESTIMATION;

PARAFFINS;

EID: 8344241988     PISSN: 00207608     EISSN: None     Source Type: Journal    
DOI: 10.1002/qua.20236     Document Type: Conference Paper

References (134)

1. (a) Eliel E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994;
2. (b) Juaristi, E., Ed. Conformational Behavior of Six-Membered Rings; VCH Publishers: New York, 1995;
3. Cremer, D.; Szabo, K. J. In Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995; Chapter 3 and references therein;
4. Wiberg, K. B.; Walters, V. A.; Dailey, W. P. J Am Chem Soc 1985, 107, 4860;
5. (e) Wiberg, K. B.; Hammer, J. D.; Castejon, H.; Bailey, W. F.; DeLeon, E. L.; Jarret, M. J Org Chem 1999, 64, 2085;
6. (f) Freeman, F.; Kasner, M. L.; Tsegai, Z. M.; Hehre, W. J. J Chem Ed 2000, 77, 661;
7. (g) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A: Structure and Mechanisms, 4th ed.; Kluwer Academic/Plenum: New York, 2000; Chapter 3;
8. (h) Pickett, H. M.; Strauss, H. L. J Am Chem Soc 1970, 92, 7281;
9. Squillacote, M.; Sheridan, R. S.; Chapman, O. L.; Anet, F. A. L. J Am Chem Soc 1975, 97, 3244;
10. (j) Cremer, D.; Pople, J. A. J Am Chem Soc 1975, 97, 1354;
11. (k) Chiu, N. S.; Ewbank, J. D.; Schäfer, L. J Mol Struct 1982, 86, 397;
12. Dixon, D. A.; Komornicki, A. J Phys Chem 1990, 94, 5630;
13. Ferguson, D. M.; Gould, I. R.; Glauser, W. A.; Schroeder, S.; Kollman, P. A. J Comput Chem 1992, 13, 525;
14. (n) Leventis, N.; Hanna, S. B.; Sotiriou-Leventis, C. J Chem Ed 1997, 74, 813-814;
15. (o) Sauers, R. R. J Chem Ed 2000, 77, 332
16. (a) Tribble, M. T.; Allinger, N. L. Tetrahedron 1972, 28, 2147;
17. (b) Ouellette, R. J.; Baron, D.; Stolfo, J.; Rosenblum, A.; Weber, P. Tetrahedron 1972, 28, 2163;
18. Ouellette, R. J. J. Am Chem Soc 1974, 96, 2421;
19. Lambert J. B.; Featherman, S. I. Chem Rev 1975, 75, 611;
20. (e) Shen, Q.; Hilderbrandt, R. L.; Mastryukov, V. S. J Mol Struct 1979, 54, 121;
21. (f) Cho, S. G. Bull Korean Chem Soc 1995, 16, 905;
22. (g) Arnason, I.; Thorarinsson, G. K.; Matern, E. Z Anorg Allg Chem 2000, 626, 853;
23. (h) Frierson, M. R.; Iman, M. S.; Zalkow, V. B.; Allinger, N. L. J Org Chem 1988, 53, 5248;
24. Carleer, R.; Anteunis, M. J. Org Magn Reson 1979, 12, 673;
25. (j) Arnason, L; Kvaran, A.; Jonsdottir, S.; Gudnason, P. I.; Oberhammer, H. J Org Chem 2002, 67, 3827;
26. (k) Jensen, F. R.; Bushweller, C. H. Tetrahedron Lett 1968, 2825;
27. Bushweller, C. H.; O'Neil, J. W.; Bilofsky, H. S. Tetrahedron 1972, 28, 2163.
28. Hehre, W J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003.
29. Schlegel, H. B. J Comput Chem 2003, 24, 1514-1527.
30. Lewars, E. Computational Chemistry Introduction to the Theory and Applications of Molecular and Quantum Mechanics; Kluwer Academic Boston, 2003.
31. Cramer, C. J. Essentials of Computational Chemistry Theories and Models; Wiley: New York, 2002.
32. Young, D. Computational Chemistry: A Practical Guide for Applying Techniques to Real-World Problems; Wiley-Interscience: New York, 2001.
33. Jensen, F. Introduction to Computational Chemistry; Wiley: New York, 1998.
34. Hehre, W. J.; Radom, L.; Schleyer, P. v.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
35. (a) Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, C. D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Domboski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.; Byrd, E. F. C; Voorhis, T. V.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J Comput Chem 2000, 21, 1532;
36. (b) The Spartan '02 Macintosh and Spartan '02 Unix programs are available from Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; 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.; Andres, J. L.; Gonzalez, C; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
38. (a) Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996;
39. (b) Frisch, A.; Frisch, M. J. Gaussian 98 User's Reference, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1999.
40. (a) Ayala, P. Y.; Schlegel, H. B. J Chem Phys 1997, 107, 375;
41. (b) Gonzalez, C.; Schlegel H. B. J Chem Phys 1989, 90, 2154;
42. Gonzalez, C.; Schlegel, H. B. J Phys Chem 1990, 94, 5523;
43. Gonzalez, C.; Schlegel, H. B. J Phys Chem 1991, 95, 5583.
44. Lynch, B. J.; Fast, P. L.; Harris, M; Truhlar, D. G. J Phys Chem A 2000, 104, 4811-4815.
45. (a) Becke, A. D. J Chem Phys 1993, 98, 5648;
46. (b) Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1988, 37, 785.
47. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J Phys Chem 1994, 98, 11 623.
48. Curtiss, L. A.; Raghavachari, K.; Refern, P. C.; Pople, J. A. J Chem Phys 1997, 106, 1063.
49. Truhlar, D. G. Faraday Discuss Chem Soc 1998, 110, 362.
50. Baker, J.; Muir, M.; Andzelm, J.; Scheiner, A. ACS Symp Ser 1996, 629, 342.
51. Skokov, S.; Wheeler, R. A. Chem Phys Lett 1997, 271, 251.
52. Wiberg, K. B.; Castejon, H.; Bailey, W. F.; Ochterski, J. J Org Chem 2000, 65, 1181.
53. Jonas, V.; Frenking, G. Chem Phys Lett 1991, 127, 175.
54. Freeman, F.; Goomaroni, F. Struct Chem 2002, 13, 115.
55. (a) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: New York, 2000;
56. (b) Bauschlicher, C. W., Jr.; Partridge, H. J Chem Phys 1995, 103, 1788;
57. Rauhut, G.; Pulay, P. J Phys Chem 1995, 99, 3093;
58. Scott, A. P.; Radom, L. J Phys Chem 1996, 100, 16502;
59. (e) Wong, M. W. Chem Phys Lett 1996, 256, 391;
60. (f) Jaramillo, J.; Scuseria, G. E. Chem Phys Lett 1999, 312, 269;
61. (g) Florian, J.; Johnson, B. G. J Phys Chem 1995, 99, 5899.
62. (a) Freeman, F.; Phornvoranunt, A.; Hehre, W. J. J Phys Org Chem 1998, 11, 831;
63. (b) Freeman, P.; Phornvoranunt, A.; Hehre, W. J. J Phys Org Chem 1999, 12, 176;
64. Freeman, F.; Hehre, W. J. J Mol Struct (Theochem) 2000, 529, 225;
65. Freeman, F.; Derek, E. Struct Chem. 2003, 14, 497-510 and references cited therein.
66. (a) Cuevas, G.; Juaristi, E. J Am Chem Soc 2002, 124, 13088 and references cited therein;
67. (b) Alabugin, I. V. J Org Chem 2000, 65, 3910 and references cited therein;
68. Alabugin, I. V.; Zeidan, T. A. J Am Chem Soc 2002, 124, 3175 and reference cited therein;
69. Chertkov, V. A.; Sereyev, N. M. J Am Chem Soc 1977, 99, 6750-6752.
70. Cramer, C. J. J Mol Struct (Theochem) 1996, 370, 135-146.
71. Kirby, A. J. Stereoelectronic Effects; Oxford: New York, 1996.
72. Freeman, F.; Kasner, M. L.; Hehre, W. J. J Phys Chem A 2001, 105, 10123.
73. Freeman, F.; Derek, E. J Comput Chem 2003, 24, 909.
74. (a) Wiberg, K. B.; Hadad, C. M.; LePage, T. J.; Breneman, C. M.; Frisch, M. J. J Phys Chem 1992, 96, 671;
75. (b) Breneman, C. M.; Wiberg, K. B. J Comput Chem 1990, 11, 361;
76. Mulliken, R. S. J Chem Phys 1955, 23, 1833, 1841, 2338, 2343;
77. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J Chem Phys 1985, 83, 735-746;
78. (b) Reed, A. E.; Weinhold, F. J Am Chem Soc 1985, 107, 919;
79. Reed, A. E.; Weinhold, F. J Am Chem Soc 1986, 108, 3586;
80. Carpenter, J. C.; Weinhold, F. J Mol Struct (Theochem) 1988, 169, 41;
81. (e) Singh, U. C.; Kollman, P. A. J Comput Chem 1984, 5, 129;
82. (f) Besler, B. H.; Merz, K. M., Jr.; Kollman, P. A. J Comput Chem 1990, 11, 431;
83. (g) Gronert, S.; Glaser, R.; Streitweiser, A. J Am Chem Soc 1989, 111, 3111-3117;
84. (h) Bader, R. W. F. Atoms in Molecules. A Quantum Theory; Clarendon Press: Oxford, 1994;
85. Geerlings, P.; De Proft, F.; Martin, J. M. L. In Recent Developments and Applications of Modern Density Functional Theory; Seminario, J. M., Ed.; Elsevier: Amsterdam, 1996; Chapter 22;
86. (j) Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J Comput Chem 2003, 24, 1291-1304.
87. Freeman, F.; Le, K. T. J Phys Chem A 2003, 107, 2908-2918 and references cited therein.
88. Freeman, F.; Cha, C. Int J Quantum Chem 2004, 96, 443-455.
89. Freeman, F.; Cha, C. J Phys Org Chem 2004, 17, 32-41.
90. (a) Pophristic, V.; Goodman, L.; Guchgait, N. J Phys Chem A 1997, 101, 4290-4297;
91. (b) Goodman, L.; Pophristic, V. Chem Phys Lett 1996, 259, 287;
92. Sovers, O. J.; Kern, C. W.; Pitzer, R. M.; Karplus, M. J Chem Phys 1968, 49, 2592;
93. Bader, R. F. W.; Cheeseman, J. R.; Laidig, K. E.; Wiberg, K. B.; Breneman, C. J Am Chem Soc 1990, 112, 6530;
94. (e) Luke, B. T.; Pople, J. A.; Krogh-Jesperson, M. B.; Apeloig, Y.; Chandrasejhar, J.; Schleyer, P. v. R. J Am Chem Soc 1986, 108, 260;
95. (f) Knight, E. T.; Allen, L. C. J Am Chem Soc 1995, 117, 4401.
96. Bent, H. A. Chem Rev 1961, 61, 275.
97. Thomas, H. D.; Chen, K.; Allinger, N. L. J Am Chem Soc 1994, 116, 5887.
98. Frierson, M. R.; Iman, M. R.; Zalkow, V. B.; Allinger, N. L. J Org Chem 1988, 53, 5248.
99. (a) Allinger, N. L.; Hickey, M. J. J Am Chem Soc 1975, 97, 5167;
100. (b) Chen, K.; Allinger, N. L. J Phys Org Chem 1997, 10, 697;
101. Allinger, N. L.; Fan, Y. J Comput Chem 1997, 18, 1827.
102. (a) Yamamoto, S.; Nakata, M.; Fukuyama, T.; Kuchitsu, K. J Phys Chem 1985, 89, 3298;
103. th Austin Symposium on Gas Phase Molecular Structure, Austin, TX, March 1978; Paper WA6;
104. Adams, W. H.; Geise, H. J.; Bartell, L. S. J Am Chem Soc 1970, 92, 5013-5019.
105. (a) Skancke, P. N. J Phys Chem 1994, 98, 3154 and references cited therein;
106. (b) Horner, D. A.; Grev, R. S.; Schaefer, H. F. J Am Chem Soc 1992, 114, 2093;
107. Grev, R. S.; Schaefer, H. F. J Am Chem Soc 1987, 109, 6569, 6577;
108. Kitchen, D. B.; Jackson, J. E.; Allen, L. C. J Am Chem Soc 1990, 112, 3408;
109. (e) Boatz, J. A.; Gordon, M. S.; Hilderbrandt, R. L. J Am Chem Soc 1988, 110, 352;
110. (f) Boatz, J. A.; Gordon, M. S. J Phys Chem 1989, 93, 3025;
111. (g) Gordon, M. S. J Am Chem Soc 1980, 102, 7419;
112. (h) Nagase, S.; Nakano, M. J. J Chem Soc, Chem Commun 1988, 1077;
113. Cremer, D.; Gauss, J.; Cremer, E. J. Mol. Struct; (Theochem) 1988, 169, 531;
114. (j) Schoeller, W. W.; Dabisch, T. Inorg Chem 1987, 26, 1081;
115. (k) Jones, P. R.; White, D. D. J Organomet Chem 1979, 181, 399;
116. Eckert-Maksic, M.; Kovacevic, K.; Maksic, Z. B. J Organomet Chem 1979, 1681, 295;
117. Delker, G. L.; Wang, Y.; Stucky, G. D.; Lambert, R. L., Jr.; Haas, C. K.; Seyferth, D. J Am Chem Soc 1976, 98, 1779-1784;
118. (n) Ishikawa, M.; Matsuzawa, S.; Sugisawa, H.; Yano, F.; Kamitori, S.; Higuchi, T. J Am Chem Soc 1985, 107, 7706-7710;
119. (o) Lukevics, E. Main Group Metal Chem 1998, 21, 649-727.
120. (a) Morino, Y.; Kuchitsu, K.; Yokozeki, A. Bull Chem Soc Jpn 1967, 40, 1552;
121. (b) Fitch, A. N.; Jobic, H. J Chem Soc, Chem Commun 1993, 1516-1517;
122. Chiang, J. F.; Wilcox, C. F., Jr.; Bauer, S. H. J Am Chem Soc 1968, 90, 3149-3157;
123. Ikeura, T.; Tanaka, K.; Hirota, E.; Inaba, S.-L; Nagai, Y. Bull Chem Soc Jpn 1977, 50, 1309-1314.
124. Hilderbrandt, R. L.; Homer, G. D.; Boujouk, P. J Am Chem Soc 1976, 98, 7475.
125. Vilkov, L. V.; Mastryukov, V. S.; Baurova, Y. V.; Vdovin, V. M.; Grinberg, P. L. Proc Acad Sci SSR (Engl Trans) 1967, 177, 1146.
126. Pringle, W. C., Jr. J Chem Phys 1971, 54, 4979.
127. Lanne, J.; Lord, R. C. J Chem Phys 1968, 48, 1508.
128. Egawa, T.; Fukuyama, T.; Yamamoto, S.; Takabayashi, F.; Kambara, H.; Ueda, T.; Kuchitsu, K. J Chem Phys 1987, 86, 6018.
129. (a) Durig, J. R.; Willis, J. N., Jr. J Mol Spectrosc 1969, 32, 320;
130. (b) Durig, J. R; Lafferty, W. J.; Kalansky, V. V. J Phys Chem 1976, 80, 1199.
131. Pitzer, K. S.; Donath, W. E. J Am Chem Soc 1959, 81, 3213.
132. (a) Fuchs, B. Top Stereochem 1978, 10, 1;
133. (b) Riddell, F. G. The Conformational Analysis of Heterocydic Compounds; Academic New York, 1978;
134. Riddel, F. G. In Cyclic Organonitrogen Stereodynamics; Lambert J. B., Takeuchi, Y., Eds.; VCH: New York, 1992; p 159.