Tandem pseudopericyclic reactions: [1,5]-X sigmatropic shift/6π- electrocyclic ring closure converting N-(2-X-carbonyl)phenyl ketenimines into 2-X-quinolin-4(3H)-ones

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8126-8139

  Alajarín, Mateo ^a   Ortín, María Mar ^a   Sánchez Andrada, Pilar ^a   Vidal, Ángel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; ENERGY BARRIERS; KETENIMINES; PSEUDOPERICYCLIC REACTIONS;

AMINO ACIDS; CHEMICAL BONDS; COMPUTATION THEORY; KETONES; REACTION KINETICS; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

AMIDE; AMINE; CARBONYL DERIVATIVE; CHLORIDE; FLUORIDE; HYDROXYL GROUP; IMINE; KETENE DERIVATIVE; OXAZINE DERIVATIVE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDONE DERIVATIVE; QUINOLINE DERIVATIVE; SELENIUM DERIVATIVE; SOLVENT; TOLUENE; VINYL DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION KINETICS; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ENERGY; GEOMETRY; HEATING; MAGNETISM; REACTION ANALYSIS; RING CLOSING METATHESIS; THERMODYNAMICS;

EID: 33750005055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061286e     Document Type: Article

References (134)

1. For reviews on the chemistry of ketenimines, see: (a) Krow, D. R. Angew. Chem., Int. Ed. Engl. 1971, 10, 435-449.
2. (b) Gambaryan, N. P. Usp. Khim. 1976, 45, 1251-1268.
3. (c) Dondoni, A. Heterocyles 1980, 14, 1547-1566.
4. (d) Barker, M. W.; McHenry, W. E. In The Chemistry of Ketenes, Allenes and Related Compounds; Patai, S., Ed.; Wiley-Interscience: Chichester, U.K., 1980; Part 2, p 701.
5. (e) Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. 2000, 4, 293-326.
6. (a) Alajarín, M.; Vidal, A.; Ortín, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030.
7. (b) Alajarín, M.; Vidal, A.; Ortín, M.-M. Org. Biomol. Chem. 2003, 1, 4282-4292.
8. (c) Alajarín, M.; Vidal, A.; Ortín, M.-M.; Bautista, D. New J. Chem. 2004, 28, 570-577.
9. (d) Alajarín, M.; Vidal, A.; Ortín, M.-M.; Bautista, D. Synlett 2004, 991-994.
10. (a) Aumann, R. Chem. Ber. 1993, 126, 1867-1872.
11. (b) Merlic, C. A.; Burns, E. E. Tetrahedron Lett. 1993, 34, 5401-5404.
12. Brannock, K. C.; Burpitt, R. D. J. Org. Chem. 1965, 30, 2564-2565.
13. (a) Walters, M. A.; McDonough, C. S.; Brown, P. S., Jr.; Hoem, A. B. Tetrahedron Lett. 1991, 32, 179-182.
14. (b) Walters, M. A.; Hoem, A. B.; Arcand, H. R.; Hegeman, A. D.; McDonough, C. S. Tetrahedron Lett. 1993, 34, 1453-1456.
15. (c) Walters, M. A.; Hoem, A. B. J. Org. Chem. 1994, 59, 2645-2647.
16. (d) Walters, M. A. J. Am. Chem. Soc. 1994, 116, 11618-11619.
17. (e) Walters, M. A. J. Org. Chem. 1996, 61, 978-983.
18. (a) Molina, P.; Alajarín, M.; López-Leonardo, C. Tetrahedron Lett. 1991, 32, 4041-4044.
19. (b) Molina, P.; Alajarín, M.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1993, 49, 5153-5168.
20. Nubbemeyer, U. Synthesis 1993, 1120-1128.
21. (a) Cheikh, A. B.; Chuche, J.; Manisse, N.; Pommelet, J. C.; Netsch, K.-P.; Lorencak, P.; Wentrup, C. J. Org. Chem. 1991, 56, 970-975.
22. (b) Kappe, C. O.; Kollenz, G.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 487-488.
23. (c) Kappe, C. O.; Kollenz, G.; Netsch, K.-P.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 488-490.
24. (d) Fulloon, B.; El-Nabi, H. A. A.; Kollenz, G.; Wentrup, C. Tetrahedron Lett. 1995, 36, 6547-6550.
25. (e) Fulloon, B. E.; Wentrup, C. J. Org. Chem. 1996, 61, 1363-1368.
26. (f) Ramana Rao, V. V.; Wentrup, C. J. Chem. Soc., Perkin Trans. 1 1998, 2583-2586.
27. (g) Wentrup, C.; Ramana Rao, V. V.; Frank, W.; Fulloon, B. E.; Moloney, D. W. J.; Mosandl, T. J. Org. Chem. 1999, 64, 3608-3619.
28. (h) Finnerty, J. J.; Wentrup, C. J. Org. Chem. 2004, 69, 1909-1918.
29. For other papers dealing with [1,3]-migration in ketenimines, see: (i) Aumann, R.; Heinen, H. Chem. Ber. 1988, 121, 1739-1743.
30. (j) Clarke, D.; Mares, R. W.; McNab, H. J. Chem. Soc., Chem. Commun. 1993, 1026-1027.
31. (k) Clarke, D.; Mares, R. W.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1997, 1799-1804.
32. (l) Amsallem, D.; Mazières, S.; Piquet-Fauré, V.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. Chem.-Eur. J. 2002, 8, 5306-5311.
33. The Conrad-Limpach synthesis of quinolones by pyrolysis of esters probably proceeds via imidoyl ketene intermediates: Conrad, M.; Limpach, L. Ber. Dtsch. Chem. Ges. 1887, 20, 944-948.
34. The first report on the observation of imidoyl ketenes in quinolone synthesis: Briehl, H.; Adelheid, L.; Wentrup, C. J. Org. Chem. 1984, 49, 2772-2779.
35. Goerdeler, J.; Lindner, C.; Zander, F. Chem. Ber. 1981, 114, 536-548.
36. Morel, G.; Marchand, E.; Foucaud, A. J. Org. Chem. 1985, 50, 771-778.
37. Ramana Rao, V. V.; Fulloon, B. E.; Bernhardt, P. V.; Koch, R.; Wentrup, C. J. Org. Chem. 1998, 63, 5779-5786.
38. Alajarín, M.; Ortín, M.-M.; Sánchez-Andrada, P.; Vidal, A.; Bautista, D. Org. Lett. 2005, 7, 5281-5284.
39. The experimental work related with the [1,5]-migration of alkyl(aryl)thio groups in N-[2-alkyl(aryl)thiocarbonyl]phenyl ketenimines has been reported in our preliminary communication, ref 13.
40. We did not succeed in the synthesis of the Se-aryl 2-azidoselenobenzoates 2k,1 by using other well-established reaction conditions for the preparation of selenoesters, such as those used in the following articles: (a) Grieco, P. A.; Jaw, J. Y. J. Org. Chem. 1981, 46, 1215-1217.
41. (b) Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A. Tetrahedron 1985, 41, 4835-4841.
42. (c) Gais, H.-J. Angew. Chem., Int. Ed. Engl. 1977, 16, 244-246.
43. (d) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285-3294.
44. Probably the o-azido group of 1 interferes with the expected substitution at the acyl group. Only a modification of the experimental procedure described by Odom for the preparation of selenoesters from acyl chlorides and benzeneselenolates, generated by reaction of diaryl diselenides and sodium borohydride, provided the Se-aryl 2-azidoselenobenzoates 2k,1, although in very low yields, see: (e) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811-816.
45. We have reported that a similar ring closure transforming N-β-(methyleneaminoacyl)vinyl ketenimine into 6-methyleneamino-2-methylene- 1,3-oxazine takes place trough a transition state of pseudopericyclic topology and low energy barrier; see: Alajarín, M.; Sánchez-Andrada, P.; Vidal, A.; Tovar, F. J. Org. Chem. 2005, 70, 1340-1349.
46. (a) Saettel, N. J.; Wiest, O. J. Org. Chem. 2000, 65, 2331-2336.
47. (b) Hess, B. A.; Baldwin, J. E. J. Org. Chem. 2002, 67, 6025-6033.
48. (c) Jursic, B. S. THEOCHEM 1998, 423, 189-194.
49. (d) Jensen, F.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 3139-3140.
50. For comparative purposes, we have also optimized the transition state corresponding to the [1,5]-H migration in 1,3-pentadiene, although it has been extensively studied previously by others (see ref 17 and references cited herein).
51. (a) Rodríguez-Otero, J. J. Org. Chem. 1999, 64, 6842-6848.
52. (b) Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 11529-11535.
53. (c) Evanseck, J. D.; Thomas, B. E., IV; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1995, 60, 7134-7141.
54. (d) Jefford, C. W.; Bernardinelli, G.; Wang, Y.; Spellmeyer, D. C.; Buda, A.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1157-1165.
55. (e) Baldwin, J. E.; Reddy, V. P.; Schaad, L. J.; Hess, B. A. J. Am. Chem. Soc. 1988, 110, 8554-8555.
56. (a) An analogous finding was accomplished in the study of the effect of several substituents in the vinylketene-acylallene rearrangement reported by Wentrup et al.: the [1,3]-shift in the dimethylamino group takes place involving the formation of a zwitterionic intermediate. See: Bibas, H.; Wong, M. W.; Wentrup, C. Chem.-Eur. J. 1997, 3, 237-248.
57. (b) Recently, Wentrup et al. have also found zwitterionic intermediates in the [1,3]-shifts of amino and dimethylamino groups in the imidoylketene-acyl ketenimine rearrangement; see: Finnerty, J. F.; Wentrup, C. J. Org. Chem. 2005, 70, 9735-9739.
58. (a) Koch, R.; Wentrup, C. Org. Biol. Chem. 2004, 2, 195-199.
59. (b) Nguyen, M. T.; Landuyt, L.; Nguyen, H. M. T. Eur. J. Org. Chem. 1999, 401-407.
60. For similar [1,3]-sigmatropic shifts occurring in other heterocumulenes see: (c) Koch, R.; Wentrup, C. J. Chem. Soc., Perkin Trans. 2 2000, 1846-1850.
61. (d) Ammann, J. R.; Flammang, R.; Wong, M. W.; Wentrup, C. J. Org. Chem. 2000, 65, 2706.
62. (e) Wong, M. W.; Wentrup, C. J. Org. Chem. 1994, 59, 5279-5285.
63. (f) Bibas, H.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1995, 117, 9582-9583.
64. (g) Finnerty, J.; Andraos, J.; Yamamoto, Y.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1998, 120, 1701-1704.
65. -1; see ref 12.
66. Pseudopericyclic reactions lack cyclic orbital overlap and have four characteristics, as stated by Birney: (1) all are allowed, (2) they have nonaromatic transition states, (3) they may have very low barriers, and (4) they may have planar transition states. (a) For Lemal's definition of a pseudopericyclic process, see: Ross, J. A.; Seiders, R. P.; Lemal, D. M. J. Am. Chem. Soc. 1976, 98, 4325-4327.
67. For other examples of pseudopericyclic reactions, see, for example: (b) Birney, D. M.; Wagenseiler, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
68. (c) Birney, D. M. J. Org. Chem. 1994, 59, 2557-2564.
69. (d) Wagenseller, P. E.; Birney, D. M.; Roy, J. Org. Chem. 1995, 60, 2853-2859.
70. (e) Birney, D. M. J. Org. Chem. 1996, 61, 243-251.
71. (f) Birney, D. M.; Xu, X.; Ham, S. Angew. Chem., Int. Ed. 1999, 38, 189-193.
72. (g) Alajarín, M.; Sánchez-Andrada, P.; Cossío, F. P.; Arrieta, A.; Lecea, B. J. Org. Chem. 2001, 66, 8470-8477.
73. See, for example: (a) Bornemann, H.; Wentrup, C. J. Org. Chem. 2005, 70, 5862-5868.
74. (b) Wei, H.-X.; Zhou, C.; Ham, H.; White, J. M.; Birney, D. M. Org. Lett. 2004, 6, 4289-4292.
75. (c) Birney, D. M. Org. Lett. 2004, 6, 851-854.
76. (d) Birney, D. M. J. Am. Chem. Soc. 2000, 122, 10917-10925.
77. (e) Shumway, W.; Ham, S.; Moer, J.; Wittlesey, B. R.; Birney, D. M. J. Org. Chem. 2000, 65, 7731-7739.
78. (f) Alajarín, M.; Vidal, A.; Sánchez-Andrada, P.; Tovar, F.; Ochoa, G. Org. Lett. 2000, 2, 965-968.
79. (g) Bibas, H. K.; Wentrup, C. J. Org. Chem. 1998, 63, 2619-2626.
80. (h) Birney, D. M.; Ham, S.; Unruh, G. R. J. Am. Chem. Soc. 1997, 119, 4509-4517.
81. (i) Luo, L.; Bartberger, M. D.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1997, 119, 12366-12367.
82. (j) Ham, S.; Birney, D. M. J. Org. Chem. 1996, 61, 3962-3968.
83. (k) Koch, R.; Wong, M. H.; Wentrup, C. J. Org. Chem. 1996, 61, 6809-6813.
84. (l) Wagenseller, P. E.; Birney, D. M.; Roy, D. J. Org. Chem. 1995, 60, 2853-2859.
85. (a) Sadavisam, D. V.; Birney, D. M. Org. Lett. 2005, 7, 5817-5820.
86. (b) Alajarín, M.; Sánchez-Andrada, P.; López- Leonardo, C.; Álvarez, A. J. Org. Chem. 2005, 70, 7617-7623.
87. (c) Fukushima, K.; Iwahashi, H. Heterocydes 2005, 65, 2605-2618.
88. (d) Cabaleiro-Lago, E. M.; Rodríguez-Otero, J.; González-López, I.; Peña-Gallego, A.; Hermida-Ramón, J. M. J. Phys. Chem. A 2005, 109, 5636-5644.
89. (e) Zhou, C.; Birney, D. M. J. Org. Chem. 2004, 69, 86-89.
90. (f) Peña-Gallego, A.; Rodríguez-Otero, J.; Cabaleiro-Lago, E. M. J. Org. Chem. 2004, 69, 7013-7017.
91. (g) Rodriguez-Otero, J.; Cabaleiro-Lago, E. M. Chem.-Eur. J. 2003, 9, 1837-1843.
92. (h) De Lera, A. R.; Cossío, F. P. Angew. Chem., Int. Ed. 2002, 41, 1150-1152.
93. (i) Zhou, C.; Birney, D. M. J. Am. Chem. Soc. 2002, 124, 5231-5241.
94. (j) Fabian, W. M. F.; Kappe, C. O.; Bakulev, V. A. J. Org. Chem. 2000, 65, 47-53.
95. (k) Fabian, W. M. F.; Bakulev, V. A.; Kappe, C. O. J. Org. Chem. 1998, 63, 5801-5805.
96. (a) Herges, R.; Geuenich, D. J. Phys. Chem. A 2001, 105, 3214-3220.
97. (b) Herges, R.; Papafilippopoulos, A. Angew. Chem., Int. Ed. 2001, 40, 4671-4674.
98. (c) Kimball, D. B.; Merges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572-1573.
99. (a) Kimball, D. M.; Weakley, T. J. R.; Merges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 13463-13473.
100. (b) Cabaleiro-Lago E. M.; Rodríguez-Otero, J.; García-López, R. M.; Peña-Gallego, A.; Hermida-Ramon, J. M. Chem.-Eur. J. 2005, 11, 5966-5974.
101. (c) Cabaleiro-Lago, E. M.; Rodríguez-Otero, J.; Varela-Varela, S. M.; Peña-Gallego, A.; Hermida-Ramón, J. M. J. Org. Chem. 2005, 70, 3921-3928.
102. (d) Peña-Gallego, A.; Rodríguez-Otero, J.; Cabaleiro-Lago, E. M. Eur. J. Org. Chem. 2005, 3228-3232.
103. (a) Chamorro, E. E.; Notario, R. J. Phys. Chem. A 2004, 108, 4099-4104.
104. (b) Cárdenas, C.; Chamorro, E.; Notario, R. J. Phys. Chem. A 2005, 109, 4352-4358.
105. (c) Matito, E.; Sola, M.; Duran, M.; Poater, J. J. Phys. Chem. B 2005, 109, 7591-7593.
106. (d) Rode, J. E.; Dobrowolski, J. Cz. J. Phys. Chem. A 2006, 110, 207-218.
107. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318.
108. (b) Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669-12670.
109. (c) Schleyer, P. v. R.; Manoharn, M.; Wang, Z.-X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Org. Lett. 2001, 3, 2465-2468.
110. (d) See also Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Org. Lett. 2005, 7, 863-866 and references herein.
111. (a) Morao, I.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1997, 62, 7033-7036.
112. (b) Morao, I.; Cossío, F. P. J. Org. Chem. 1999, 64, 1868-1874.
113. (c) Cossío, F. P.; Morao, L; Jiao, H.; Scheleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6737-6746.
114. (d) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossío, F. P. J. Am. Chem. Soc. 2000, 122, 6078-6092.
115. (e) de Lera, A. R.; Alvarez, R.; Lecea, B.; Torrado, A.; Cossío, F. P. Angew. Chem., Int. Ed. 2001, 40, 557-561.
116. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Clarendon Press: Oxford, 1990; pp 13-52.
117. See, for example: (a) Montero-Campillo, M. M.; Rodríguez-Otero, J.; Cabaleiro-Lago, E. M. J. Phys. Chem. A 2004, 108, 8373-8377.
118. (b) Zora, M. J. Org. Chem. 2004, 69, 1940-1947.
119. (c) Cossío, F. P.; Alonso, C.; Lecea, B.; Ayerbe, M.; Rubiales, G.; Palacios, F. J. Org. Chem. 2006, 71, 2839-2847.
120. Jiao, H.; Schleyer, P. v. R. J. Chem. Soc., Faraday Trans. 1994, 90, 1559-1567.
121. Jiao, H.; Schleyer, P. v. R. J. Phys. Chem. 1998, 11, 655-662.
122. Reva, I.; Breda, S.; Roseiro, T.; Eusebio, E.; Fausto, R. J. Org. Chem. 2005, 70, 7701-7710.
123. Zora, M.; Sahpaz, F.; Ozarslan, E. J. Mol. Structure (THEOCHEM) 2002, 589-590, 111-112.
124. 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.; 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.; Gonzalez, C.; 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.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
125. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; 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.; 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, L.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M. P.; Gill, M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
126. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. In Ab Initio Molecular Orbital Theory; Wiley: New York, 1986, pp 71-82, and references therein.
127. (a) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
128. (b) Bartolotti, L. J.; Fluchichk, K. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyds, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7; pp 187-216.
129. (c) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phvs. Chem. 1996, 100, 12974-12980.
130. (d) Ziegler, T. Chem. Rev. 1991, 91, 651-667.
131. (a) Redd, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
132. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
133. (c) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434-1445.
134. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.