The substitution effect on heavy versions of cyclobutadiene

International Journal of Quantum Chemistry

Volumn 110, Issue 8, 2010, Pages 1514-1528

  Nazari, Fariba ^a   Doroodi, Zohreh ^b  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

AIM; BLYP; Cyclobutadiene; Heavy versions of cyclobutadiene; NBO; NICS

Indexed keywords

BUTADIENE; CALCULATIONS; CARRIER CONCENTRATION; CHEMICAL ANALYSIS; CHLORINE COMPOUNDS; CRYSTAL ATOMIC STRUCTURE; DIHEDRAL ANGLE; ELECTRON DENSITY MEASUREMENT; HYDROGEN BONDS; MAGNESIUM COMPOUNDS;

BLYP; CYCLOBUTADIENES; ELECTRONIC CHARACTERISTICS; INTERAMOLECULAR INTERACTIONS; NATURAL BOND ORBITAL ANALYSIS; NICS; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS; TOPOLOGICAL PARAMETERS;

DENSITY FUNCTIONAL THEORY;

EID: 77951545370     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.22271     Document Type: Article

References (128)

1. Schleyer, P. v. R. Chem Rev 2001, 101, 1115.
2. Schleyer, P. v. R. Chem Rev 2005, 105, 3433.
3. Fattahi, A.; Lis, L.; Tian, Z.; Kass, S. R. Angew Chem Int Ed 2006, 45, 4984.
4. Carsky, P.; Bartlett, R. J.; Fitzgerald, G.; Noga, J.; Spirko, V. J Chem Phys 1998, 89, 3008.
5. Balková, A.; Bartlett, R. J. J Chem Phys 1994, 101, 8972.
6. Sancho-García, J. C.; Pérez-Jiménez, A. J.; Moscardó, F. Chem Phys Lett 2000, 317, 245.
7. Sancho-García, J. C.; Pittner, J.; Hubac, I.; Cársky, P. J Chem Phys 2000, 112, 8785.
8. Eckert-Maksić, M.; Vazdar, M.; Barbatti, M.; Lischka, H.; Maksić, Z. B. J Chem Phys 2006, 125, 64310.
9. Li, Y.; Li, Z.-R.; Wu, D.; Chen, W.; Sun, C.-C. J Mol Struct 2006, 758, 21.
10. Sommerfeld, T. J Am Chem Soc 2002, 124, 1119.
11. Jung, Y.; Heine, T.; Schleyer, P. v. R.; Head-Gordan, M. J Am Chem Soc 2004, 126, 3132.
12. Maier, G. Angew Chem Int Ed Engl 1988, 27, 309.
13. Maier, G.; Fleischer, F. Tetrahedron Lett 1991, 32, 57.
14. Maier, G.; Born, D.; Bauer, I.; Wolf, R.; Boese, R.; Cremer, D. Chem Ber 1994, 127, 173.
15. Maier, G.;Wolf, R.; Kalinowski, H.-O.; Boese, R. Chem Ber 1994, 127, 191.
16. Maier, G.; Wolf, R.; Kalinowski, H.-O. Chem Ber 1994, 127, 201.
17. Maier, G.; Rang, H.; Emrich, R. Liebigs Ann 1995, 153.
18. Maier, G.; Rang, H.; Emrich, R.; Irngartinger, H. Liebigs Ann 1995, 161.
19. Maier, G.; Fleischer, F. Liebigs Ann 1995, 169.
20. Maier, G.; Rang, H.; Fleischer, F.; Kalinowski, H.-O. Liebigs Ann 1995, 173.
21. Maier, G.; Emrich, R.; Malsch, K.-D.; Schneider, K.-A.; Nixdorf, M.; Irngartinger, H. Chem Ber 1988, 118, 2798.
22. Cremer, D.; Kraka, E.; Joo, H.; Stearns, J. A.; Zwier, T. S. Phys Chem Chem Phys 2006, 8, 5304.
23. Koehler, F.; Herges, R.; Stanger A. J Phys Chem A 2007, 111, 5116.
24. Seal, P.; Chakrabarti, S. J Phys Chem A 2007, 111, 5119.
25. Irwin, R. M.; Cooke, J. M.; Laane, J. J Am Chem Soc 1977, 99, 3273.
26. Kollmar, H.; Staemmler, V. J Am Chem Soc 1977, 99, 3583.
27. Borden, W. T.; Davidson, E. R.; Hart, P. J Am Chem Soc 1978, 100, 388.
28. Fratev, F.; Monev, V.; Janoschek, R. Tetrahedron 1982, 38, 2929.
29. Andes Hess, B.; Čársky, P.; Schaad, L. J. J Am Chem Soc 1983, 105, 695.
30. Glukhovtsev, M. N.; Laiter, S.; Pross, A. J Phys Chem 1995, 99, 6828.
31. Voter A. F.; Goddard, W. A. J Am Chem Soc 1986, 108, 2830.
32. Metropolous, A.; Chiu, Y.-N. J Mol Struct 1997, 417, 95.
33. Rishard, M. Z. M.; Irwin, R. M.; Laane, J. J Phys Chem A 2007, 111, 825.
34. Bally, T. Angew Chem Int Ed 2006, 45, 6616.
35. Shiota, Y.; Kondo, M.; Yoshizawa, K. J Chem Phys 2001, 115, 9243.
36. Kovaèeviæ, B.; Bariæ, D.; Maksiæ, Z. B.; Müller, T. J Phys Chem A 2004, 108, 9126.
37. Maksiæ, Z. B.; Bariæ, D.; Petanjek, I. J Phys Chem A 2000, 104, 10873.
38. Levchenko, S. V.; Krylov, A. I. J Chem Phys 2004, 120, 175.
39. Watts, L.; Fitzpatrick, J. D.; Pettit, R. J Am Chem Soc 1965, 87, 3253.
40. Jursic, B. S. J Mol Struct 2000, 507, 185.
41. Andes Hess, B, Jr.; Schaad, L. J Org Lett 2001, 4, 735.
42. Seal, P.; Chakrabarti, S. J Phys Chem A 2007, 111, 9988.
43. Hohlneicher, G.; Packschiesb, L.; Weber, J. Phys Chem Chem Phys 2007, 9, 2517.
44. Wiberg, K. B.; Marquez, M. J Am Chem Soc 1998, 120, 2932.
45. James Petersson, E.; Fanuele, J. C.; Nimlos, M. R.; Lemal, D. M.; Barney Ellison, G.; George Radziszewski, J. J Am Chem Soc 1997, 119, 11122.
46. Herrera, O. M.; Brinn, I. M. J Chem Soc Perkin Trans I 1986, 145, 1683.
47. Bally, T.; Masamune, S. Tetrahedron 1980, 36, 343.
48. Kollmar, H.; Carrion, F.; Dewar, M. J. S.; Bingham, R. C. J Am Chem Soc 1981, 103, 5292.
49. Seal, P.; Chakrabarti, S. J Phys Chem A 2007, 111, 715.
50. Irngartinger, H.; Rodewald, H. Angew Chem Int Ed Engl 1974, 13, 740.
51. Balci, M.; McKee, M. L.; Schleyer, P. v. R. J Phys Chem A 2000, 104, 1246.
52. Hengge, E.; Janoschek, R. Chem Rev 1995, 95, 1495.
53. Kickelbick, G. Angew Chem Int Ed 2005, 44, 6804.
54. Sari, L.; McCarthy, M. C.; Schaefer, H. F, III; Thaodeus, P. J Am Chem Soc 2003, 125, 11409.
55. Xu, W. G.; Yang, J. C.; Xiao, W. S. J Phys Chem A 2004, 108, 11345.
56. Wong, H.-W.; Nieto, J. C. A.; Swihart, M. T.; Broadbelt, L. J. J Phys Chem A 2004, 108, 874.
57. Chambreau, S. D.; Wang, L.; Zhang, J. J Phys Chem A 2002, 106, 5081.
58. Naruse, Y.; Ma, J.; Inagaki, S. J Phys Chem A 2003, 107, 2860.
59. Wang, W. N.; Tang, H. R.; Fan, K. N.; Iwata, S. J Chem Phys 2001, 114, 1278.
60. Tang, M.; Lu, W.; Wang, C. Z.; Ho, K. M. Chem Phys Lett 2003, 377, 413.
61. Xu, C.; Taylor, T. R.; Burton, G. R.; Neumark, D. M. J Chem Phys 1998, 108, 7645.
62. Kessels, W. M. M.; Van de Sanden, M. C. M.; Schram, D. C. Appl Phys Lett 1998, 72, 2397.
63. Ma, B.; Allinger, N. L.; Schaefer, H. F, III. J Chem Phys 1996, 105, 5731.
64. Pak, C.; Rienstra-Kiracofe, J. C.; Schaefer, H. F., III. J Phys Chem A 2000, 104, 11232.
65. Sari, L.; Gonzales, J. M.; Yamaguchi, Y.; Schaefer, H. F., III. J Chem Phys 2001, 114, 4472.
66. Collins, S.; Dutler, R.; Rauk, A. J Am Chem Soc 1987, 109, 2564.
67. Swihart, M. T. J Phys Chem A 2000, 104, 6083.
68. Onida, G.; Andreoni, W. Chem Phys Lett 1995, 243, 183.
69. Koch, R.; Bruhn, T.; Weidenbruch, M. J Mol Struct 2004, 680, 91.
70. Zhai, H.-J.; Kuznetsov, A. E.; Boldyrev, A. I.; Wang, L.-S. ChemPhysChem 2004, 5, 1885.
71. Rohlfing, C. M.; Raghavachari, K. J Chem Phys 1992, 96, 2114.
72. RohIfing, C. M.; Raghavachari, K. Chem Phys Lett 1990, 167, 559.
73. Raghavachari, K. J Chem Phys 1986, 84, 5672.
74. Raghavachari, K.; Logovinsky, V. Phys Rev Lett 1985, 55, 2853.
75. Raghavachari, K. J Chem Phys 1985, 83, 3520.
76. Lerner, H.-W. Coord Chem Rev 2005, 249, 781.
77. Fournier, R.; Sinnott, S. B.; DePristo, A. E. J Chem Phys 1992, 97, 4149.
78. Li, S. D.; Johnston, R. L.; Murrell, J. N. J Chem Soc Faraday Trans 1992, 88, 1229.
79. (a) Adamowicz, L. Chem Phys Lett 1992, 188, 131
80. (b) Adamowicz, L. Chem Phys Lett 1991, 185, 244.
81. Katircioglu, S.; Erkoc, S. Chem Phys Lett 1991, 184, 118.
82. Sekiguchi, A.; Matsuno, T.; Ichinohe, M. J Am Chem Soc 2000, 122, 11250.
83. Pacchioni, G.; Koutecky, J. J Chem Phys 1986, 84, 3301.
84. Tanaka, R.; lwamoto, T.; Kira, M. Angew Chem Int Ed Engl 2006, 45, 6371.
85. Slanina, Z. Chem Phys Lett 1986, 131, 420.
86. Grev, R. S.; Schaefer, H. F. Chem Phys Lett 1985, 119, 111.
87. Jones, R. O. Phys Rev A 1985, 32, 2589.
88. Arnold, C. C.; Neumark, D. M. J Chem Phys 1993, 99, 3353.
89. Clabo, D. A.; Schaefer, H. F. J Am Chem Soc 1986, 108, 4344.
90. Yates, B. F.; Clabo, D. A, Jr.; Schaefer, H. F. Chem Phys Lett 1988, 143, 421.
91. Yates, B. F.; Schaefer, H. F, III. Chem Phys Lett 1989, 155, 563.
92. Sax, A. F.; Kalcher, J. J Comput Chem 1986, 10, 309.
93. Zhao, M.; Gimarc, B. M. Inorg Chem 1996, 35, 5378.
94. Nagase, S.; Nakano, M.; Kudo, T. J Chem Soc Chem Commun 1987, 2, 60.
95. Nagnse, S.; Nakano, M. Angew Chem Int Ed Engl 1988, 27,1081.
96. Ohanessian, G.; Hiberty, P. C.; Lefour, J. M.; Flament, J.-P.; Shaik, S. S. Inorg Chem 1988, 27, 2219.
97. Jemmis, E. D.; Srinivas, G. N. J Am Chem Soc 1996, 118, 3738.
98. Schleyer, P. v. R.; Sax, A. F.; Kalcher, J.; Janoschek, R. Angew Chem Int Ed Engl 1987, 26, 364.
99. Li, C. P.; Yang, J. C.; Bai, X. J Mol Struct 2005, 755, 65.
100. Xu, C.; Taylor, T. R.; Burton, G. R.; Neumark, D. M. J Chem Phys 1998, 108, 1395.
101. Hohenberg, P.; Kohn, W. Phys Rev 1964, 136B, 864.
102. Kohn, W.; Sham, L. J. Phys Rev A 1965, 140, 1133.
103. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
104. Pople, J. A.; Gill, P. M. W.; Johnson, B. G. Chem Phys Lett 1992, 199, 557.
105. Becke, A. D. J Chem Phys 1993, 98, 5648 .
106. Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian: Pittsburgh, PA., 1996.
107. 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.; 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.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B. 03; Gaussian, Inc.: Pittsburgh PA, 2003.
108. NBO. 3.1, Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Theoretical Chemistry Institute; University of Wisconsin: Madison, WI, 1996.
109. Reed, A. E.; Weinhold, F. J Chem Phys 1985, 83, 1736.
110. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev 1988, 88, 899.
111. Weinhold, F. In Encyclopedia of computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; Vol.3, p 1792.
112. Matta, C. F.; Boyd, R. J. The Quantitative Theory of Atoms in Molecules; Wiley-VCH: Weinheim, 2007;
113. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
114. Biegler-Konig, F.; Schoenbohm, J. AIM2000, 2nd ed.; Buro fur Innovative Software: Bielefeld, Germany, 2002.
115. Sax, A. F.; Kalcher, J. J Chem Soc Chem Commun 1987, 11, 809.
116. Liyanage, P. S.; Silva, R. M. D.; Silva, K. M. N. D. J Mol Struct 2003, 639, 195.
117. Hinchliffe, A.; Munn, R. W. Mulecular Electromagnetism; Wiley: Chichester, 1985.
118. Garral, P. J. Aromaticity; Wiley: New York, 1986.
119. Minkin, V. L.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity: Electronic and Structural Aspects; Wiley: New York, 1994.
120. Schleyer, P. v. R.; Jiao, H. Pure Appl Chem 1996, 68, 209.
121. Krygowski, T. M.; Cyranski, M. K.; Czarnocki, Z.; Hafelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783.
122. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Eikema Hommes, N. J. R. V. J Am Chem Soc 1996, 118, 6317.
123. Poater, J.; Fradera, X.; Duran, M.; Sola, M. Chem Eur J 2003, 9, 400.
124. Cyranski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J Org Chem 2002, 67, 1333.
125. Schleyer, P. v. R.; Jiao, H.; Eikema Hommes, N. J. R. V.; Malkin, V. G.; Malkina, O. L. J Am Chem Soc 1997, 119, 12669.
126. Wolinski, K.; Hilton, J. F.; Pulay, P. J Am Chem Soc 1990, 112, 8251.
127. Parr, R. G.; Szentpaly, L. V.; Liu, S. J Am Chem Soc 1999, 121, 1922.
128. Chattaraj, P. K.; Roy, D. R.; Elango, M.; Subramanian, V. J. Phys Chem A 2005, 109, 9590.