Tautomerism and the maximum hardness principle

International Journal of Quantum Chemistry

Volumn 106, Issue 8, 2006, Pages 1723-1735

  Zhang, Yi Liang ^a   Yang, Zhong Zhi ^b  

^a JILIN UNIVERSITY   (China)

^b LIAONING NORMAL UNIVERSITY   (China)

Author keywords

Atom bond electronegativity equalization method; Conformer; Energy; Hardness; Maximum hardness principle; Stability; Tautomer

Indexed keywords

CHEMICAL BONDS; MONOMERS; QUANTUM THEORY;

ATOM-BOND ELECTRONEGATIVITY EQUALIZATION METHOD; CONFORMER; ENERGY; MAXIMUM HARDNESS PRINCIPLE; TAUTOMER;

HARDNESS;

EID: 33646248903     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.20952     Document Type: Article

References (127)

1. (a) Pearson, R. G. Coord Chem Rev 1990, 100, 403;
2. (b) Pearson, R. G. Inorg Chim Acta 1995, 240, 93;
3. (c) Sen, K. D., Ed. Chemical Hardness: Structure and Bonding 80; Springer-Verlag: Berlin, 1993;
4. (d) Pearson, R. G. Chemical Hardness: Applications from Molecules to Solids; Wiley-VCH: Weinheim, 1997.
5. Pearson, R. G., Ed. Hard and Soft Acids and Bases; Dowden, Hutchinson and Ross: Stroudsburg, PA, 1973.
6. (a) Pearson, R. G. J Chem Educ 1987, 64, 561;
7. (b) Pearson, R. G. Acc Chem Res 1993, 26, 250;
8. (c) Parr, R. G.; Zhou, Z. X. Acc Chem Res 1993, 26, 256;
9. (d) Pearson, R. G. J Chem Educ 1999, 76, 267.
10. (a) Politzer, P. J Chem Phys 1987, 86, 1072;
11. (b) Simón-Manso, Y.; Fuentealba, P. J Phys Chem A 1998, 102, 2029.
12. Chattaraj, P. K.; Sengupta, S. J Phys Chem 1996, 100, 16126.
13. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
14. Parr, R. G.; Pearson, R. G. J Am Chem Soc 1983, 105, 7512.
15. (a) Nalewajski, R. F. J Am Chem Soc 1984, 106, 944;
16. (b) Chattaraj, P. K.; Lee, H.; Parr, R. G. J Am Chem Soc 1991, 113, 1855;
17. (c) Gázquez, J. L. Struct Bonding 1993, 80, 27;
18. (d) Gázquez, J. L.; Méndez, F. J Phys Chem 1994, 98, 4591;
19. (e) Li, Y.; Evans, J. N. S. J Am Chem Soc 1995, 117, 7756;
20. (f) Gázquez, J. L. J Phys Chem A 1997, 101, 4657;
21. (g) Cedillo, A.; Chattaraj, P. K.; Parr, R. G. Int J Quantum Chem 2000, 77, 403.
22. (a) Parr, R. G.; Chattaraj, P. K. J Am Chem Soc 1991, 113, 1854;
23. (b) Chattaraj, P. K.; Liu, G. H.; Parr, R. G. Chem Phys Lett 1995, 237, 171;
24. (c) Parr, R. G.; Gázquez, J. L. J Phys Chem 1993, 97, 3939;
25. (d) Liu, S.; Parr, R. G. J Chem Phys 1997, 106, 5578;
26. (e) Ayers, P. W.; Parr, R. G. J Am Chem Soc 2000, 122, 2010.
27. (a) Zhou, Z. X.; Parr, R. G.; Garst, J. F. Tetrahedron Lett 1988, 29, 4843;
28. (b) Zhou, Z. X.; Parr, R. G. J Am Chem Soc 1989, 111, 7371;
29. (c) Datta, D. J Phys Chem 1992, 96, 2409;
30. (d) Pearson, R. G.; Palke, W. E. J Phys Chem 1992, 96, 3283;
31. (e) Pal, S.; Vaval, N.; Roy, R. J Phys Chem 1993, 97, 4404;
32. (f) Chattaraj, P. K.; Nath, S.; Sannigrahi, A. B. Chem Phys Lett 1993, 212, 223;
33. (g) Chandra, A. K. J Mol Struct (Theochem) 1994, 312, 297;
34. (h) Chattaraj, P. K.; Nath, S.; Sannigrahi, A. B. J Phys Chem 1994, 98, 9143;
35. (i) Cárdenas-Jirón, G. I.; Lahsen, J.; Toro-Labbé, A. J Phys Chem 1995, 99, 5325;
36. (j) Kar, T.; Scheiner, S. J Phys Chem 1995, 99, 8121;
37. (k) Makov, G. J Phys Chem 1995, 99, 9337;
38. (1) Cárdenas-Jirón, G. I.; Toro-Labbé, A. J Phys Chem 1995, 99, 12730;
39. (m) Ghanty, T. K.; Ghosh, S. K. J Phys Chem 1996, 100, 12295;
40. (n) Cárdenas-jirón, G. I.; Lahsen, J.; Toro-Labbé, A. J Mol Struct (Theochem) 1997, 390, 79;
41. (o) Cárdenas-Jirón, G. I.; Letelier, J. R.; Toro-Labbé, A. J Phys Chem A 1998, 102, 7864;
42. (p) Chattaraj, P. K.; Fuentealba, P.; Jaque, P.; Toro-Labbé, A. J Phys Chem A 1999, 103, 9307;
43. (q) Chattaraj, P. K.; Fuentealba, P.; Gómez, B.; Contreras, R. J Am Chem Soc 2000, 122, 348;
44. (r) Fuentealba, P.; Simón-Manso, Y.; Chattaraj, P. K. J Phys Chem A 2000, 104, 3185;
45. (s) Gutiérrez-Oliva, S.; Jaque, P.; Toro-Labbé, A. J Phys Chem A 2000, 104, 8955;
46. (t) Chattaraj, P. K.; Maiti, B. J Phys Chem A 2001, 105, 169;
47. (u) Kolandaivel, P.; Senthilkumar, K. J Mol Struct (Theochem) 2001, 535, 61;
48. (v) Yu, D.; Chen, Z. D. J Mol Struct (Theochem) 2001, 540, 29;
49. (w) Chattaraj, P. K.; Pérez, P.; Zevallos, J.; Toro-Labbé, A. J Phys Chem A 2001, 105, 4272;
50. (x) Chattaraj, P. K.; Gómez, B.; Chamorro, E.; Santos, J.; Fuentealba, P. J Phys Chem A 2001, 105, 8815;
51. (y) Kanakaraju, R.; Kolandaivel, P. J Mol Struct (Theochem) 2003, 623, 39;
52. (z) Anandan, K.; Kolandaivel, P.; Kumaresan, R.; Gowenlock, B. G. J Mol Struct (Theochem) 2004, 680, 149.
53. (a) Pérez, P.; Toro-Labbé, A. J Phys Chem A 2000, 104, 1557;
54. (b) Pérez, P.; Toro-Labbé, A. Theor Chem Acc 2001, 105, 422;
55. (c) Senthilkumar, K.; Kolandaivel, P. J Computer-Aided Mol Design 2002, 16, 263.
56. (a) Chattaraj, P. K.; Cedillo, A.; Parr, R. G. Chem Phys 1996, 204, 429;
57. (b) Cárdenas-Jiron, G. I.; Gutiérrez-Oliva, S.; Melin, J.; Toro-Labbé, A. J Phys Chem A 1997, 101, 4621;
58. (c) Mineva, T.; Sicilia, E.; Russo, N. J Am Chem Soc 1998, 120, 9053;
59. (d) Chattaraj, P. K.; Poddar, A. J Phys Chem A 1999, 103, 1274;
60. (e) Cong, Y.; Yang, Z. Z.; Wang, C. S.; Liu, X. C.; Bao, X. H. Chem Phys Lett 2002, 357, 59;
61. (f) Chattaraj, P. K.; Sarkar, U. Int J Quantum Chem 2003, 91, 633;
62. (g) Chattaraj, P. K.; Maiti, B. J Am Chem Soc 2003, 125, 2705;
63. (h) Hohm, U. J Phys Chem A 2000, 104, 8418;
64. (i) Chattaraj, P. K.; Nath, S. Chem Phys Lett 1994, 217, 342;
65. (j) Chattaraj, P. K.; Cedillo, A.; Parr, R. G.; Arnett, E. M. J Org Chem 1995, 60, 4707;
66. (k) Pérez, P.; Contreras, R. Chem Phys Lett 1996, 256, 15;
67. (l) Nguyen, L. T.; Le, T. N.; De Proft, F.; Chandra, A. K.; Langenaeker, W.; Nguyen, M. T.; Geerlings, P. J Am Chem Soc 1999, 121, 5992;
68. (m) Jaque, P.; Toro-Labbé, A. J Phys Chem A 2000, 104, 995;
69. (n) Chattaraj, P. K.; Sengupta, S.; Poddar, A. J Mol Struct (Theochem) 2000, 501, 339;
70. (o) Aliste, M. P. J Mol Struct (Theochem) 2000, 507, 1;
71. (p) Portier, J.; Campet, G.; Kwon, C. W.; Etourneau, J.; Subramanian, M. A. Int J Inorg Mat 2001, 3, 1091;
72. (q) Ghanty, T. K.; Ghosh, S. K. J Phys Chem A 2002, 106, 4200;
73. (r) Jaque, P.; Toro-Labbé, A. J Chem Phys 2002, 117, 3208;
74. (s) Chattaraj, P. K.; Pérez, P.; Zevallos, J.; Toro-Labbé, A. J Mol Struct (Theochem) 2002, 580, 171;
75. (t) Singh, P. P.; Srivastava, H. K.; Pasha, F. A. Bioorg Med Chem 2004, 12, 171;
76. (u) Van Cauter, K.; Hemelsoet, K.; Van Speybroeck, V.; Reyniers, M. F.; Waroquier, M. Int J Quantum Chem 2005, 102, 454;
77. (v) Pasha, F. A.; Srivastava, H. K.; Singh, P. P. Int J Quantum Chem 2005, 104, 87.
78. (a) Kar, T.; Scheiner, S.; Sannigrahi, A. B. J Phys Chem A 1998, 102, 5967;
79. (b) Subramanian, V.; Sivanesan, D.; Amutha, R.; Padmanabhan, J.; Ramasami, T. Chem Phys Lett 1998, 294, 285;
80. (c) Solà, M.; Toro-Labbé, A. J Phys Chem A 1999, 103, 8847;
81. (d) Jayakumar, N.; Kolanadaivel, P. Int J Quantum Chem 2000, 76, 648;
82. (e) Sicilia, E.; Russo, N.; Mineva, T. J Phys Chem A 2001, 105, 442;
83. (f) Torrent-Sucarrat, M.; Luis, J. M.; Duran, M.; Solà, M. J Am Chem Soc 2001, 123, 7951;
84. (g) Uchimaru, T.; Chandra, A. K.; Kawahara, S.; Matsumura, K.; Tsuzuki, S.; Mikami, M. J Phys Chem A 2001, 105, 1343;
85. (h) Torrent-Sucarrat, M.; Luis, J. M.; Duran, M.; Solà, M. J Chem Phys 2002, 117, 10561;
86. (i) Aizman, A.; Contreras, R.; Galván, M.; Cedillo, A.; Santos, J. C.; Chamorro, E. J Phys Chem A 2002, 106, 7844;
87. (j) Biancafort, L.; Torrent-Sucarrat, M.; Luis, J. M.; Duran, M.; Solà, M. J Phys Chem A 2003, 107, 7337;
88. (k) Senthilkumar, L.; Kolandaivel, P. J Mol Struct (Theochem) 2003, 638, 69;
89. (l) Gómez, B.; Fuentealba, P.; Contreras, R. Theor Chem Acc 2003, 110, 421;
90. (m) Anandan, K.; Kolandaivel, P.; Kumaresan, R. J Mol Struct (Theochem) 2004, 686, 83;
91. (n) Kolandaivel, P.; Knapp-Mohammady, M.; Suhai, S. Int J Quantum Chem 2004, 99, 28;
92. (o) Selvarengan, P.; Kolandaivel, P. J Mol Struct (Theochem) 2004, 671, 77;
93. (p) Selvarengan, P.; Kolandaivel, P. Bioorg Chem 2005, 33, 253;
94. (q) Torrent-Sucarrat, M.; Duran, M.; Luis, J. M.; Solà, M. J Phys Chem A 2005, 109, 615;
95. (r) Anandan, K.; Kolandaivel, P.; Kumaresan, R. Int J Quantum Chem 2005, 103, 127;
96. (s) Anandan, K.; Kolandaivel, P.; Kumaresan, R. Int J Quantum Chem 2005, 104, 286;
97. (t) Noorizadeh, S. J Mol Struct: THEOCHEM 2005, 713, 27.
98. (a) Sebastian, K. L. Chem Phys Lett 1994, 231, 40;
99. (b) Sebastian, K. L. Chem Phys Lett 1995, 236, 621.
100. (a) Wade, L. G., Jr. Organic Chemistry, 5th ed.; Pearson: Upper Saddle River, NJ, 2003;
101. (b) Brown, W. H.; Foote, C. S. Organic Chemistry, 2nd ed.; Saunders College: Fort Worth, TX, 1998;
102. (c) Loudon, G. M. Organic Chemistry, 2nd ed.; WA Benjamin/Cummings: Menlo Park, CA, 1988.
103. Pearson, R. G. J Am Chem Soc 1963, 85, 3533.
104. Yang, Z. Z.; Wang, C. S. J Phys Chem A 1997, 101, 6315.
105. Parr, R. G.; Yang, W. J Am Chem Soc 1984, 106, 4049.
106. 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.05, Gaussian, Inc.: Pittsburgh, PA, 2003.
107. (a) Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 2001;
108. (b) Conant, J. B.; Thompson, A. F., Jr. J Am Chem Soc 1932, 54, 4039;
109. (c) Branch, G. E. K.; Calvin, M. The Theory of Organic Chemistry: An Advanced Course; Prentice-Hall: Englewood Cliffs, NJ, 1941;
110. (d) Valters, R. E.; Flitsch, W. Ring-Chain Tautomerism; Plenum: New York, 1985;
111. (e) Katritzky, A. R.; Rees, C. W., Eds.; Comprehensive Heterocyclic Chemistry, Vol. 2; Pergamon: Oxford, 1984;
112. (f) Wheland, G. W. Advanced Organic Chemistry, 2nd ed.; John Wiley & Sons: New York, 1949;
113. (g) Gilchrist, T. L. Heterocyclic Chemistry; Pitman: London, 1985;
114. (h) Reutov, O. Theoretical Principles of Organic Chemistry; Mir: Moscow, 1970;
115. (i) Hückel, W. Theoretical Principles of Organic Chemistry, Vol. I; Elsevier: Amsterdam, The Netherlands, 1955;
116. (j) Beak, P. Acc Chem Res 1977, 10, 186;
117. (k) Schreck, R. J Am Chem Soc 1949, 71, 1881;
118. (l) Karelson, M.; Maran, U.; Katritzky, A. R. Tetrahedron 1996, 52, 11325;
119. (m) Theissling, C. B.; Nibbering, N. M. M. Tetrahedron Lett 1977, 18, 1777;
120. (n) Tobias, S.; Günther, H. Tetrahedron Lett 1982, 23, 4785;
121. (o) Schwarzenbach, von G.; Wittwer, Ch. Helv Chim Acta 1947, 30, 663;
122. (p) Cook, M. J.; Katritzky, A. R.; Taagepera, M.; Singh, T. D.; Taft, R. W. J Am Chem Soc 1976, 98, 6048;
123. (q) Capon, B.; Guo, B.-Z.; Kwok, F. C.; Siddhanta, A. K.; Zucco, C. Acc Chem Res 1988, 21, 135;
124. (r) Kresge, A. J. Acc Chem Res 1990, 23, 43.
125. (a) Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960;
126. (b) Allred, A. L. J Inorg Nucl Chem 1961, 17, 215.
127. Belova, N. V.; Oberhammer, H.; Girichev, G. V. J Phys Chem A 2004, 108, 3593.