Hypervalent adducts of chalcogen-containing peri -substituted naphthalenes; Reactions of sulfur, selenium, and tellurium with dihalogens

Inorganic Chemistry

Volumn 49, Issue 16, 2010, Pages 7577-7596

  Knight, Fergus R ^a   Fuller, Amy L ^a   Bühl, Michael ^a   Slawin, Alexandra M Z ^a   Woollins, J Derek ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77955491432     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101086h     Document Type: Article

References (161)

1. Lewis, G. N. J. Am. Chem. Soc. 1916, 38, 762
2. Langmuir, I. J. Am. Chem. Soc. 1919, 41, 868
3. Jensen, W. B. J. Chem. Educ. 2006, 83, 1751
4. Musher, J. I. Angew. Chem., Int. Ed. Engl. 1969, 8, 54
5. Inorganic Chemistry; Shriver, D. F. and Atkins, P. W., Eds.; Oxford University Press: Oxford, U. K., 1999; chapter 3, p 70.
6. Basic Inorganic Chemistry; Cotton, F. A., Wilkinson, G., and Gaus, P. L., Eds.; John Wiley & Sons, Inc.: New York, 1995; p 74.
7. Lewis, G. N. In Valence and the Structure of Atoms and Molecules; The Chemical Catalog Co.: New York, 1923; chapter 8.
8. Langmuir, I. Science 1921, 54, 59
9. Hatch, R. J. and Rundle, R. E. J. Am. Chem. Soc. 1951, 73, 4321
10. Rundle, R. E. J. Am. Chem. Soc. 1963, 85, 112
11. Rundle, R. E. J. Am. Chem. Soc. 1947, 69, 1327
12. Mooney, R. C. L. Z. Kristallogr. 1935, 90, 143
13. Mooney, R. C. L. ibid 1937, 98, 324
14. Pauling, L. In The Nature of the Chemical Bond, 3 rd ed.; Pauling, L., Ed.; Cornell University Press: Ithaca, NY, 1960; chapter 7.
15. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542
16. Sugden, S. In The Parachor and Valency; Knopf: New York, 1930; chapter 6.
17. Pimental, G. C. J. Chem. Phys. 1951, 19, 446
18. Coulson, C. A. d-Orbitals in Chemical Bonding. In Proceedings of the Robert A. Welch Foundation Conferences on Chemical Research. XVI. Theoretical Chemistry; Mulligen, W. O., Ed.; Houston, TX, 1972; chapter 3.
19. Brill, T. B. J. Chem. Educ. 1973, 50, 392
20. Kutzelnigg, W. Angew. Chem., Int. Ed. 1984, 23, 272
21. Valency and Bonding; Weinhold, F. and Landis, C., Eds.; Cambridge University Press: Cambridge, U.K., 2005; chapter 3.
22. Nakanishi, W. In Handbook of Chalcogen Chemistry, New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F. A., Ed.; RSC Publishing: Cambridge, U. K., 2007; chapter 10.3 and references cited therein.
23. Lippolis, V. and Isaia, F. In Handbook of Chalcogen Chemistry; Devillanova, F. A., Ed.; RSC Publishing: Cambridge, U. K., 2007; chapter 8.2 and references cited therein.
24. Smith, D. W. J. Chem. Educ. 2005, 82, 1202
25. Gillespie, R. J. and Robinson, E. A. Inorg. Chem. 1995, 34, 978
26. Noury, S., Silvi, B., and Gillespie, R. J. Inorg. Chem. 2002, 41, 2164
27. Chemistry of Hypervalent Compounds; Akiba, K.-Y., Ed.; Wiley-VCH: New York, 1999.
28. Landrum, G. A., Goldberg, N., and Hoffmann, R. J. Chem. Soc., Dalton Trans. 1997, 3605
29. Svensson, P. H. and Kloo, L. Chem. Rev. 2003, 103, 1649
30. Perkins, C. W., Martin, J. C., Arduengo, A. J., Law, W., Alegrie, A., and Kocki, J. K. J. Am. Chem. Soc. 1980, 102, 7753
31. Boyle, P. D. and Godfrey, S. M. Coord. Chem. Rev. 2001, 223, 265 and references cited therein.
32. Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Mancini, A. Bioinorg. Chem. Appl. 2007, 2007, 17416
33. Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Verani, G. J. Am. Chem. Soc. 2002, 124, 4538
34. Aragoni, M. C., Arca, M., Devillanova, F. A., Isaia, F., Lippolis, V., Mancini, A., Pala, L., Slawin, A. M. Z., and Woollins, J. D. Chem. Commun. 2003, 2226
35. Demartin, F., Deplano, P., Devillanova, F. A., Isaia, F., Lippolis, V., and Verani, G. Inorg. Chem. 1993, 32, 3694
36. Bigoli, F., Demartin, F., Deplano, P., Devillanova, F. A., Isaia, F., Lippolis, V., Mercuri, M. L., Pellinghelli, M. A., and Trogu, E. F. Inorg. Chem. 1996, 35, 3194
37. Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Verani, G. Trends Inorg. Chem. 1999, 6, 1 and references cited therein.
38. Boyle, P. D., Christie, J., Dyer, T., Godfrey, S. M., Howson, I. R., McArthur, C., Omar, B., Pritchard, R. G., and Williams, G. Rh. J. Chem. Soc., Dalton Trans. 2000, 3106
39. Daga, V., Hadjikakou, S. K., Hadjiliadis, N., Kubicki, M., dos Santos, J. H. Z., and Butler, I. S. Eur. J. Inorg. Chem. 2002, 1718
40. Khun, N., Fawzi, R., Kratz, T., Steimann, M., and Henkel, G. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 112, 225
41. du Mont, W.-W. Main Group Chem. News 1994, 2, 18
42. Demartin, F., Devillanova, F. A., Isaia, F., Lippolis, V., and Verani, G. Inorg. Chim. Acta 1997, 255, 203
43. Ouvrard, C., Le Questel, J.-Y., Berthelot, M., and Laurence, C. Acta Crystallogr., Sect. B: Struct. Sci. 2003, B59, 512
44. Näther, C. and Bolte, M. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 453
45. Khun, N., Kratz, T., and Henkel, G. Z. Naturforsch. B, Chem. Sci. 1996, 51, 295
46. Aragoni, M. C., Arca, M., Blake, A. J., Devillanova, F. A., du Mont, W. -W., Garau, A., Isaia, F., Lippolis, V., Verani, G., and Wilson, C. Angew. Chem., Int. Ed. Engl. 2001, 40, 4229
47. Nakanishi, W., Hayashi, S., and Kihara, H. J. Org. Chem. 1999, 64, 2630
48. Nakanishi, W., Hayashi, S., Tukada, H., and Iwamura, H. J. Phys. Org. Chem. 1990, 3, 358
49. Nakanishi, W., Yamamoto, Y., Hayashi, S., Tukada, H., and Iwamura, H. J. Phys. Org. Chem. 1990, 3, 369
50. Nakanishi, W. and Hayashi, S. J. Organomet. Chem. 2000, 611, 178
51. Nakanishi, W. and Hayashi, S. Heteroat. Chem. 2001, 12, 369
52. Nakanishi, W., Hayashi, S., and Kusuyama, Y. J. Chem. Soc., Perkin Trans. 2 2002, 262
53. Laur, P. H., Saberi-Niaki, S. M., Scheiter, M., Hu, C., Englert, U., Wang, Y., and Fleischhauer, J. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1035
54. Rudd, M. D., Linderman, S. V., and Husebye, S. Acta Chem. Scand. 1997, 51, 689
55. Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lelj, F., Lippolis, V., and Verani, G. Chem. -Eur. J. 2001, 7, 3122
56. Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Verani, G. Dalton Trans. 2005, 2252
57. Baenziger, M. C., Buckles, R. E., Maner, R. J., and Simpson, T. D. J. Am. Chem. Soc. 1969, 91, 5749
58. Allred, A. L. and Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 5, 264
59. Allred, A. L. and Rochow, E. G. J. Inorg. Nucl. Chem. 1958, 5, 269
60. Allen, D. W., Berridge, R., Bricklebank, N., Forder, S. D., Palacio, F., Coles, S. J., Hursthouse, M. B., and Skabara, P. J. Inorg. Chem. 2003, 42, 3975
61. Bigoli, F., Deplano, P., Mercuri, M. L., Pellinghelli, M. A., Sabatini, A., Trogu, E. F., and Vacca, A. J. Chem. Soc., Dalton Trans. 1996, 3583
62. Blake, A. J., Devillanova, F. A., Garau, A., Gilby, L. M., Gould, R. O., Isaia, F., Lippolis, V., Parsons, S., Radek, C., and Schröder, M. J. Chem. Soc., Dalton Trans. 1998, 2037
63. Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Verani, G. J. Chem. Soc., Dalton Trans. 1999, 3069
64. Hartl, H. and Steidl, S. Z. Naturforsch. B, Chem. Sci. 1977, 32, 6
65. Lyon, E. J., Musie, G., Reibenspies, J. H., and Darensbourg, M. Y. Inorg. Chem. 1998, 37, 6942
66. Ito, S., Liang, H., and Yoshifuji, M. Chem. Commun. 2003, 398
67. Apperley, D. C., Bricklebank, N., Hursthouse, M. B., Light, M. E., and Coles, S. J. Polyhedron 2001, 20, 1907
68. Antoniadis, C. D., Corban, G. J., Hadjikakou, S. K., Hadjiliadis, N., Kubicki, M., Warner, S., and Butler, I. S. Eur. J. Inorg. Chem. 2003, 1635
69. Cross, W. I., Godfrey, S. M., Jackson, S. L., McAuliffe, C. A., and Pritchard, R. G. J. Chem. Soc., Dalton Trans. 1999, 2225
70. Corban, G. J., Hadjikakou, S. K., Hadjiliadis, N., Kubicki, M., Tiekink, E. R. T., Butler, I. S., Drougas, E., and Kosmas, A. M. Inorg. Chem. 2005, 44, 8617
71. Rmming, C. Acta Chem. Scand. 1960, 14, 2145
72. Chao, G. Y. and McCullough, J. D. Acta Crystallogr. 1961, 14, 940
73. Hope, H. and McCullough, J. D. Acta Crystallogr. 1962, 15, 806
74. Hope, H. and McCullough, J. D. Acta Crystallogr. 1964, 17, 712
75. Maddox, H. and McCullough, J. D. Inorg. Chem. 1966, 5, 522
76. Jeske, J., du Mont, W.-W., and Jones, P. G. Chem. -Eur. J. 1999, 5, 385
77. Cristiani, F., Demartin, F., Devillanova, F. A., Isaia, F., Saba, G., and Verani, G. J. Chem. Soc., Dalton Trans. 1992, 3553
78. Godfrey, S. M., McAuliffe, C. A., Pritchard, R. G., and Sarwar, S. J. Chem. Soc., Dalton Trans. 1997, 1031
79. Chemistry of the Elements; Greenwood, N. N. and Earnshaw, A., Eds.; Reed Elsevier: Oxford, U. K., 1997.
80. McCullough, J. D. and Marsh, R. E. Acta Crystallogr. 1950, 3, 41
81. Barlow, M. and Zimmermann-Barlow, I. Acta Chem. Scand. (Moscow Abstr.) 1966, 21, A103
82. Battelle, L., Knobler, C., and McCullough, J. D. Inorg. Chem. 1967, 6, 958
83. McCullough, J. D. and Hamburger, G. J. Am. Chem. Soc. 1941, 63, 803
84. Allegra, G., Wilson, G. E., Jr., Benedetti, E., Pedone, C., and Albert, R. J. Am. Chem. Soc. 1970, 92, 4002
85. Haywood, G. C. and Hendra, P. J. J. Chem. Soc. A 1969, 1760
86. Regelmann, B., Klinkhammer, K. W., and Schmidt, A. Z. Anorg. Allg. Chem. 1997, 623, 1633
87. Vaughan, G. B. M., Mora, A. J., Fitch, A. N., Gates, P. N., and Muir, A. S. J. Chem. Soc., Dalton Trans. 1999, 79
88. Vaughan, G. B. M., Mora, A. J., Fitch, A. N., Gates, P. N., and Muir, A. S. J. Chem. Soc., Dalton Trans. 1999, 79
89. Regelmann, B., Klinkhammer, K. W., and Schmid, A. Z. Anorg. Allg. Chem. 1988, 562, 42
90. Bricklebank, N., Skabara, P. J., Hibbs, D. E., Hursthouse, M. B., and Malik, K. M. A. J. Chem. Soc., Dalton Trans. 1999, 3007
91. Aucott, S. M., Milton, H. L., Robertson, S. D., Slawin, A. M. Z., Walker, G. D., and Woollins, J. D. Chem. -Eur. J. 2004, 10, 1666
92. Aucott, S. M., Milton, H. L., Robertson, S. D., Slawin, A. M. Z., and Woollins, J. D. Heteroat. Chem. 2004, 15, 530
93. Aucott, S. M., Milton, H. L., Robertson, S. D., Slawin, A. M. Z., and Woollins, J. D. Dalton Trans. 2004, 3347
94. Aucott, S. M., Kilian, P., Milton, H. L., Robertson, S. D., Slawin, A. M. Z., and Woollins, J. D. Inorg. Chem. 2005, 44, 2710
95. Aucott, S. M., Kilian, P., Robertson, S. D., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2006, 12, 895
96. Aucott, S. M., Duerden, D., Li, Y., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2006, 12, 5495
97. Kilian, P., Philp, D., Slawin, A. M. Z., and Woollins, J. D. Eur. J. Inorg. Chem. 2003, 249
98. Kilian, P., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2003, 9, 215
99. Kilian, P., Slawin, A. M. Z., and Woollins, J. D. Chem. Commun. 2003, 1174
100. Kilian, P., Slawin, A. M. Z., and Woollins, J. D. Dalton Trans. 2003, 3876
101. Kilian, P., Milton, H. L., Slawin, A. M. Z., and Woollins, J. D. Inorg. Chem. 2004, 43, 2252
102. Kilian, P., Slawin, A. M. Z., and Woollins, J. D. Inorg. Chim. Acta 2005, 358, 1719
103. Kilian, P., Slawin, A. M. Z., and Woollins, J. D. Dalton Trans. 2006, 2175
104. Knight, F. R., Fuller, A. L., Slawin, A. M. Z., and Woollins, J. D. Dalton Trans. 2009, 8476
105. Knight, F. R., Fuller, A. L., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2010, 16, 7617
106. Knight, F. R., Fuller, A. L., Slawin, A. M. Z., and Woollins, J. D. Polyhedron, 2010, 29, 1849, DOI: 10.1016/j.poly.2010.02.033.
107. Knight, F. R., Fuller, A. L., Slawin, A. M. Z., and Woollins, J. D. Polyhedron, 2010, 29, 1956, DOI: 10.1016/j.poly.2010.03.006.
108. Knight, F. R., Fuller, A. L., Bühl, M., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2010, 16, 7503
109. Knight, F. R., Fuller, A. L., Bühl, M., Slawin, A. M. Z., and Woollins, J. D. Chem. -Eur. J. 2010, 16, 7605
110. Organic Chemistry; Clayden, J., Greeves, N., Warren, S., and Wothers, P., Eds.; Oxford University Press: Oxford, U. K., 2001; chapter 22.
111. Organic Chemistry Structure and Function, 3 rd ed.; Vollhardt, K. P. C. and Schore, N. E., Eds.; W. H. Freeman and Company: New York, 1999; chapter 16.
112. Balasubramaniyan, V. Chem. Rev. 1966, 66, 567
113. Schmidbaur, H., Muller, H.-J., Wilkinson, D. L., Huber, B., and Müller, G. Chem. Ber. 1989, 122, 31
114. Fujihara, H. and Furukawa, N. J. Mol. Struct. 1989, 186, 261
115. Fujihara, H., Akaishi, R., Erata, T., and Furukawa, N. J. Chem. Soc., Chem. Commun. 1989, 1789
116. Handal, J., White, J. G., Franck, R. W., Yuh, Y. H., and Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 3345
117. Blount, J. F., Cozzi, F., Damewood, J. R., Iroff, D. L., Sjöstrand, U., and Mislow, K. J. Am. Chem. Soc. 1980, 102, 99
118. Anet, F. A. L., Donovan, D., Sjöstrand, U., Cozzi, F., and Mislow, K. J. Am. Chem. Soc. 1980, 102, 1748
119. Hounshell, W. D., Anet, F. A. L., Cozzi, F., Damewood, J. R., Jr., Johnson, C. A., Sjöstrand, U., and Mislow, K. J. Am. Chem. Soc. 1980, 102, 5941
120. Schröck, R., Angermaier, K., Sladek, A., and Schmidbaur, H. Organometallics 1994, 13, 3399
121. Hayashi, S. and Nakanishi, W. Bull. Chem. Soc. Jpn. 2008, 81 (12) 1605
122. Coulson, C. A., Daudel, R., and Robertson, J. M. Proc. R. Soc. London, Ser. A 1951, A207, 306
123. Cruickshank, D. W. J. Acta Crystallogr. 1957, 10, 504
124. Brock, C. P. and Dunitz, J. D. Acta Crystallogr., Sect. B: Struct. Sci. 1982, B38, 2218
125. Oddershede, J. and Larsen, S. J. Phys. Chem. A 2004, 108, 1057
126. Nagy, P., Szabó, D., Kapovits, I., Kucsman, A., Argay, G., and Kálmán, A. J. Mol. Struct. 2002, 606, 61
127. Nakanishi, W. and Hayashi, S. J. Org. Chem. 2002, 67, 38
128. Hayashi, S., Yamane, K., and Nakanishi, W. J. Org. Chem. 2007, 72, 7587
129. Nakanishi, W., Hayashi, S., and Toyota, S. J. Am. Chem. Soc. 1998, 63, 8790
130. Nakanishi, W., Hayashi, S., and Uehara, T. J. Phys. Chem. 1999, 103, 9906
131. Nakanishi, W., Hayashi, S., and Uehara, T. Eur. J. Org. Chem. 2001, 3933
132. Bondi, A. J. Phys. Chem. 1964, 68, 441
133. Roesky, H. W. and Andruh, M. Coordin. Chem., Rev. 2003, 236, 91
134. Koizumi, T., Tsutsui, K., and Tanaka, K. Eur. J. Org. Chem. 2003, 9 (18) 4528
135. Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885
136. Fuller, A. L., Knight, F. R., Slawin, A. M. Z., and Woollins, J. D. Eur. J. Inorg. Chem. 2010, accepted
137. Meinwald, J., Dauplaise, D., and Clardy, J. J. Am. Chem. Soc. 1977, 99 (23) 7743
138. Schweikert, W. W. and Meyers, E. A. J. Phys. Chem. 1968, 72, 1561
139. Bransford, J. W. and Meyers, E. A. Cryst. Struct. Commun. 1978, 7, 697
140. Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., and Verani, G. J. Chem. Soc., Dalton Trans. 1999, 3069
141. Ouvrard, C., Le Questel, J.-Y., Berthelot, M., and Laurence, C. Acta Crystallogr., Sect. B: Struct. Sci. 2003, 59, 512
142. Näther, C. and Bolte, M. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 453
143. CSD Version 5.31, Conquest 1.12 & Vista. http://www.ccdc.cam.ac.uk/ (accessed Jul 2010).
144. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G., and Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1
145. Wiberg, K. B. Tetrahedron 1968, 24, 1083
146. Fuller, A. L., Scott-Hayward, L. A. S., Li, Y., Bühl, M., Slawin, A. M. Z., and Woollins, J. D. J. Am. Chem. Soc. 2010, 132 (16) 5799
147. CrystalClear 1.6; Rigaku Corporation: Tokyo, 1999. CrystalClear Software User-s Guide, Molecular Structure Corporation: The Woodlands, TX, 2000.
148. Flugrath, J. W. P. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1999, D55, 1718
149. SIR97: Altomare, A., Burla, M., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A., Polidori, G., and Spagna, R. J. Appl. Crystallogr. 1999, 32, 115
150. DIRDIF99: Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., de Gelder, R., Israel, R., and Smits, J. M. M. The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1999.
151. CrystalStructure 3.8.1: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC: The Woodlands, TX, 2000-2006.
152. SHELX97: Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112
153. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
154. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1988, 37, 785
155. Binning, R. C. and Curtiss, L. A. J. Comput. Chem. 1990, 11, 1206
156. Reed, A. E., Curtiss, L. A., and Weinhold, F. Chem. Rev. 1988, 88, 899
157. As implemented in G03: Barone, V., Cossi, M., and Tomasi, J. J. Comput. Chem. 1998, 19, 404-417
158. Cossi, M., Scalmani, G., Rega, N., and Barone, V. J. Chem. Phys. 2002, 117, 43-54
159. Cossi, M. and Crescenzi, O. J. Chem. Phys. 2003, 19, 8863-8872
160. Boys, S. F. and Bernardi, F. Mol. Phys. 1970, 19, 553
161. 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., M. A. Al-Laham, Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C.;, and Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.