Ruthenium(II)-catalyzed selective intramolecular [2 + 2 + 2] alkyne cyclotrimerizations

Journal of the American Chemical Society

Volumn 125, Issue 40, 2003, Pages 12143-12160

  Yamamoto, Yoshihiko ^a   Arakawa, Takayasu ^a   Ogawa, Ryuji ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS; KETONES; NITRILE RESINS; POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CYCLOTRIMERIZATION;

ORGANOMETALLICS;

ACETYLENE; ALCOHOL; ALKYNE; ALKYNE DERIVATIVE; AMINE; BENZENE DERIVATIVE; ESTER; FUNCTIONAL GROUP; KETONE; NITRILE; RUTHENIUM; RUTHENIUM COMPLEX; SULFIDE; TRICYCLIC AROMATIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; CYCLOTRIMERIZATION; DENSITY; ENVIRONMENTAL TEMPERATURE; MOLECULAR INTERACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0141955235     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0358697     Document Type: Article

References (150)

1. (a) Shore, N. E. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1129-1162.
2. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 741-770.
3. (c) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100. 2901-2915.
4. (a) Trost, B. M. Science 1991. 254, 1471 -1477.
5. (b) Trost. B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
6. (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
7. Carey,. F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990; Part B, Chapter 11, pp 571-614.
8. (a) Wakatsuki. Y.; Kuramitsu, T.; Yamazaki, H. Tetrahedron Lett. 1974, 4549-4552.
9. (b) Yamazaki, H.; Wakatsuki. Y. J. Organomet. Chem. 1977, 139, 157-167.
10. (a) Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995. 361-362.
11. (b) Takahashi. T.; Xi. Z.: Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672-1680.
12. (c) Takahashi, T.; Tsai, F.-Y.; Li. Y.; Nakajima. K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093-11100.
13. (a) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925-7926.
14. (b) Tanaka, R.; Nakano, Y.; Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2002, 124, 9682-9683.
15. Gevorgyan, V.; Radhakrishnan, U.; Takeda, A.; Rubina, M.; Rubin, M.: Yamamoto, Y. J. Org. Chem. 2001, 66, 2835-2841.
16. For stoichiometric intramolecular alkyne cyclotrimerizations, see: (a) Müller, E.; Thomas, R.; Sauerbier, M.; Langer, E.; Streichfuss, D. Tetrahedron Lett. 1971, 521-524.
17. (b) Müller, E. Synthesis. 1974, 761-774 and references.
18. (c) Bhatarah, P.: Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1990, 2603-2606.
19. (d) Bhatarah. P.; Smith, E. H. J. Chem. Soc., Chem. Commun. 1991, 277-278.
20. (e) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1992, 2163-2168.
21. (f) Duckworth, D. M.; Lee-Wong, S.; Slawin, A. M. Z.; Smith, E. H.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1996, 815-821.
22. (g) Hara, R.; Guo, Q.; Takahashi, T. Chem. Lett. 2000, 140-141.
23. For catalytic intramolecular alkyne cyclotrimerizations, see: (a) Vollhardt, K. P. C.; Bergman, R. G. J. Am. Chem. Soc. 1974, 96, 4996-4998.
24. (b) Hillard, R. L., III; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1975, 14, 712-713.
25. (c) Hillard, R. L., III, Vollhardt. K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
26. (d) Grigg, R.; Scott, R.; Stevenson, P. Tetrahedron Lett. 1982, 23, 2691-2692.
27. (e) Grigg. R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364.
28. (f) Chiusoli. G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983. 8. 189-190.
29. (g) Williams, A. C.; Sheffels, P.; Sheehan, D.; Livinghouse, T. Organometallics 1989, 8, 1566-1567.
30. (h) Du Toit, C. J.; Du Plessis, J. A. K.; Lachmann, G. J. Mol, Catal. 1989, 53, 67-78.
31. (i) Badrieh, Y.; Blum, J.; Amer, I.; Vollhardt, K. P. C. J. Mol. Catal. 1991, 66, 295-312.
32. (j) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133-6135.
33. (k) Sato, Y.; Nishimata, T.; Mori, M. Heterocycles 1997, 44, 443-457.
34. (l) Nishida, M.; Shiga, H.; Mori, M. J. Org. Chem. 1998, 63, 8606-8608.
35. (m) Yamamoto, Y.; Nagata, A.; Itoh, K. Tetrahedron Lett. 1999, 40, 5035-5038.
36. (n) Yamamoto, Y.; Nagata, A.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Organometallics 2000, 19, 2403-2405.
37. (o) Ozerov, O. V,; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431.
38. (p) Takeuchi, R.; Tanaka, S.; Nakata, Y, Tetrahedron Lett, 2001, 42. 2991-2994.
39. (q) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67.
40. (r) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H, Org. Lett. 2002, 4, 807-810.
41. (s) Nishiyama, H,; Niwa, E.; Inoue, T.; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574.
42. (a) Funk, R. L.; Vollhardt, K. P, C. J. Am. Chem. Soc. 1976, 98, 6755-6757.
43. (b) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 5483-5484,
44. (c) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1979, 101, 215-217.
45. (d) Funk, R. L.: Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 5245-5253.
46. (e) Funk, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1980, 102, 5253-5261.
47. (f) Hillard, R. L., III; Parnell, C. A.; Vollhardt, K. P. C. Tetrahedron 1983, 39, 905-911.
48. (g) Halterman, R. L.; Nguyen, N. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 1379-1387.
49. (h) Lecker, S. H,; Nguyen. N. H.; Vollhardt, K. P. C. J, Am. Chem. Soc. 1986, 108, 856-858.
50. (i) Neeson, S. J.; Stevenson, P. J. Tetrahedron Lett, 1988, 29. 813-814.
51. (j) Neeson, S. J.; Stevenson, P. J, Tetrahedron 1989, 45, 6239-6248.
52. (k) McDonald, F, E.; Zhu, H. Y. H,; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
53. (l) Bradley, A,; Motherwell, W. B,: Ujjainwalla, F. Chem. Commun. 1999, 917-918.
54. (m) Petit, M.; Chouraqui, G.; Phansavath, P.; Aubert, C.; Malacria, M. Org. Lett. 2002. 4, 1027-1029.
55. (n) Witulski, B.; Zimmermann, A.; Gowans, N. D. Chem. Commun. 2002. 2984-2985.
56. (a) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564.
57. (b) Kohta, S.; Mohanraja, K.; Durani, S. Chem. Commun. 2000, 1909-1910.
58. (c) Witulski, B.; Stengel, T. Angew. Chem., lnt. Ed. 1999, 38, 2426-2430.
59. (d) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
60. (e) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859.
61. (f) Sun, Q.; Zhou, X.; Islam, K.; Kyle, D. J. Tetrahedron Lett. 2001, 42, 6495-6497.
62. (g) Turek, P.: Kotota, M.; Hocek, M,; Císarová, I. Tetahedron Lett. 2003, 44, 785-788.
63. (a) Helson, H. E.; Vollhardt, K. P. C.; Yang, Z.-Y. Angew. Chem., Int. Ed. Engl. 1985, 24, 114-115.
64. (b) Diercks, R.; Vollhardt, K. P, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 266-268.
65. (c) Hirthammer, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 2481-2482.
66. (d) Diercks. R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150-3152.
67. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis. S.; Vollhardt. K. P. C, Angew. Chem., Int. Ed. Engl. 1987, 26, 1246-1247.
68. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713-9715.
69. (g) Boese, R.; Matzger, A. J.; Mohler, D. L,: Vollhardt, K. P, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478-1481.
70. (h) Eickmeier, C.; Junga, H.; Matzger, A. J.; Scherhag, F.; Shim, M.: Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2103-2108.
71. (i) Eickmeier. C.; Holmes, D.; Junga, H.; Matzger, A. J.: Scherhag, F.; Shim, M.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1999, 38, 800-804.
72. (j) Holms, D,; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. Chem.-Eur. J. 1999, 5, 3399-3412.
73. (k) Bong, D. T,-Y.; Gentric, L.; Holms, D.; Matzger, A. J.; Scherhag, F. ; Vollhardt, K. P. C. Chem. Commun. 2002, 278-279.
74. (l) Stará, I. G.; Stary, I.; Kollárovic, A.; Teply, F.; Saman, D.; Tichy, M. J. Org. Chem. 1998, 63, 4046-4050.
75. (m) Stará, I. G.; Stary, I.; Kollárovic, A.; Teply, F.: Vyskocil, S.; Saman, D. Tetrahedron Lett. 1999, 40, 1993-1996.
76. (n) Sato. Y,; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231-5234.
77. (o) Fletcher, J. T.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 12393-12394.
78. (p) Fletcher, J. T.; Therien, M. J. Inorg. Chem. 2002, 41, 331-341.
79. (q) Fletcher, J. T,; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 4298-4311.
80. (r) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748.
81. Oshima, N.; Suzuki. H.; Moro-oka. Y. Chem. Lett. 1984, 1161-1164.
82. Preliminary results have been reported: Yamamoto, Y.; Ogawa, R. Itoh, K, Chem. Commun. 2000, 549-550.
83. Reppe, W.; Schweckendiek, W. J. Justus Liebigs Ann. Chem. 1948, 560, 104-116.
84. (a) Lindner, E.; Jansen, R.-M.; Mayer, H. A.; Hiller, W.; Fawzi, R. Organometallics 1989, 8, 2355-2360.
85. (b) Lindner, E,; Kühbauch, H. J. Organomet. Chem. 1991, 403, C9-14.
86. (c) Ren, C. Y.; Cheng, W. C.; Chan, W. C.; Yeung, C. H.; Lau, C. P. J. Mol. Catal. 1990, 59, L1-8,
87. (d) Bohanna, C.; Esteruelas, M. A.; Herrero, J.; López, A. M.; Oro, L. A. J. Organomet. Chem. 1995. 498, 199-206.
88. Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.: Vitulli, G. J. Organomet. Chem. 2000, 607, 57-63.
89. (a) Peters, J.-U.; Blechert, S. Chem. Commun. 1997, 1983-1984.
90. (b) Das, S. K.; Roy, R. Tetrahedron Lett. 1999, 40, 4015-4018.
91. (c) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965-1966.
92. (d) Hoven, G. B.; Efskind, J.; Rømming, C.; Undheim, K. J. Org. Chem. 2002, 67, 2459-2463.
93. (a) Gemel, C.; LaPensée, A.; Mauthner, K.; Mereiter, K.; Schmid, R.; Kirchner, K. Monatsh. Chem. 1997, 128, 1189-1199.
94. (b) Ernst, C.; Walter, O.; Dinjus, E. J. Prakt. Chem. 1999, 341, 801-804.
95. (c) Ernst, C.; Walter, O.; Dinjus, E. J. Organomet. Chem. 2001, 627, 249-254.
96. (c) Yamada, Y.; Mizutani, J.; Kurihara, M.; Nishihara, H. J. Organomet. Chem. 2001, 637-639, 80-83.
97. Albers, M. O.; de Waal, D. J. A.; Liles, D. C.; Robinson, D. J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986, 1680-1682.
98. Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310-4319.
99. (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6189-6190.
100. (b) Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2001, 1102-1103.
101. (a) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119.
102. (b) Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28-29.
103. Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 6844-6845.
104. The ruthenium(III) complex (lb) is commercially available and easily prepared by the literature procedure (see ref 13).
105. (a) Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080-1106.
106. (b) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
107. Wakatsuki, Y.; Yamazaki. H. J. Chem. Soc., Chem. Commun. 1973, 280.
108. Bönnemann, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 248-262.
109. (a) Dietl, H.; Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276-2285.
110. (b) Li, J.; Jiang. H.; Chen. M. J. Org. Chem. 2001, 66, 3627-3629.
111. (a) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256.
112. Also see: (b) Meyer, F. E.; de Meijere, A. Synlett 1991, 777-778.
113. (c) Torii, S.; Okumoto, H.; Nishimura, A. Tetrahedron Lett. 1991, 32, 4167-4168.
114. (d) Negishi, E.; Ay, M.; Sugihara, T. Tetrahedron 1993, 49, 5471-5482.
115. Ojima, I.; Vu, A. T.; McCullagh, J. V.; Kinoshita, A. J. Am. Chem. Soc. 1999, 121, 3230-3231.
116. Yi, C. S.; Torres-Lubian, J. R.; Liu, N. Organometallics 1998, 17, 1257-1259.
117. McAlister, D. R.: Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666-1668.
118. Hardesty, J. H.; Koerner, J. B.; Albright, T. A.; Lee, G.-Y. J. Am. Chem. Soc. 1999, 121, 6055-6067.
119. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100. 12974-12980.
120. (b) Stephen, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Phys. Chem. Lett. 1994, 98, 11623-11627.
121. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
122. (d) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
123. (e) Lee, C.: Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
124. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
125. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
126. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
127. (c) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
128. (a) Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141.
129. (b) Martin, J. M. L.; Sundermann, A. J. Chem. Phys. 2001, 114, 3408-3420.
130. (a) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
131. (b) Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294-301.
132. Alvarez, E.; Gómez, M.; Paneque, M.; Posadas, C. M.; Poveda, M. L.; Rendón N.; Santos, L. L.; Rojas-Lima, S.; Salazar, V.; Mereiter, K.; Ruiz, C. J. Am. Chem. Soc. 2003, 125, 1478-1479.
133. (a) O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307-318.
134. (b) Cheong, M.; Basolo. F. Organometallics 1988, 7, 2041-2044.
135. (c) Vest, P.; Anhaus, J.; Bajaj, H. C.; van Eldik, R. Organometallics 1991, 10, 818-819.
136. (d) Gamasa, M. P.; Gimeno, J.; Gonzalez-Bernardo, C.; Martín-Vaca, B. M.:; Monti, D.; Bassetti, M. Organometallics 1996. 15. 302-308.
137. (d) Simanko, W.; Tesch, W.; Sapunov, V. N.: Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1998, 17, 5674-5688.
138. (e) Calhorda, M. J.; Veiros, L. F. Coord. Chem. Rev. 1999, 185-186, 37-51.
139. (f) Veiros, L. F. Organometallics 2000, 19, 3127-3136.
140. (g) Veiros, L. F. Organometallics 2000, 19, 5549-5558.
141. (h) Fan, H.-J.; Hall, M. B. Orgamometallics 2001, 20, 5274-5730.
142. (a) Le Paih, J.; Dérien, S.; Dixneuf, P. H. Chem. Commun. 1999, 1437-1438.
143. (b) Mauthner. K.; Soldouzi, K. M.; Mereiter, K.; Schmid, R.: Kirchner, K. Organometallics 1999, 18, 4681-4683.
144. (c) Rüba, E.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Commun. 2001, 1996-1997.
145. (d) Rüba, E.; Mereiter, K.; Schmid, R.; Sapunov, V. N.; Kirchner, K.; Schottenberger, H.; Calhorda, M. J.; Veiros, L. F. Chem.-Eur. J. 2002, 8, 3948-3961.
146. Scheller, A.; Winter, W.; Müller, E. Liebigs Ann. Chem. 1976, 1448-1454.
147. Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, 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.; Dombroski, 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, 1532-1548.
148. Spartan '02, version 1.0.2; Wavefunction, Inc.: Irvine, CA, 2002.
149. 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 11; Gaussian, Inc.: Pittsburgh, PA, 2001.
150. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Gaussian NBO, version 3.1; Gaussian, Inc.: Pittsburgh, PA, 2001.