The Valence Bond Perspective of the Chemical Bond

The Chemical Bond: Fundamental Aspects of Chemical Bonding

Volumn 9783527333141, Issue , 2014, Pages 159-198

  Shaik, Sason ^a   Danovich, David ^a   Wu, Wei ^b   Hiberty, Philippe C ^c  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b XIAMEN UNIVERSITY   (China)

^c UNIVERSITÉ PARIS SUD   (France)

Author keywords

AIM; Bonding; Charge shift bonding; Covalent bonding; Electron pairing; Electronegativity; ELF; Ionic bonding; Lewis structures; Resonance energy; Valence bond

Indexed keywords

ATOMS; CHEMICAL BONDS; ELECTRONS; MOLECULES; POTENTIAL ENERGY;

ATOMS IN MOLECULES; BONDING; CHARGE SHIFT; CHARGE-SHIFT BONDING; COVALENT BONDING; ELECTRON LOCALIZATION FUNCTION; ELECTRON PAIRING; IONIC BONDING; LEWIS STRUCTURE; RESONANCE ENERGIES; VALENCE BONDS;

ELECTRONEGATIVITY;

EID: 84926397411     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527664696.ch5     Document Type: Chapter

References (127)

1. Shaik, S. (2007) J. Comput. Chem., 28, 51-61.
2. Shaik, S. and Hiberty, P.C. (2008) A Chemist's Guide to Valence Bond Theory, John Wiley & Sons Inc., Hoboken, NJ, pp. 1-25.
3. Sini, G., Maitre, P., Hiberty, P.C., and Shaik, S.S. (1991) J. Mol. Struct. THEOCHEM, 229, 163-188.
4. Shaik, S., Maitre, P., Sini, G., and Hiberty, P.C. (1992) J. Am. Chem. Soc., 114, 7861-7866.
5. Lauvergnat, D.L., Hiberty, P.C., Danovich, D., and Shaik, S. (1996) J. Phys. Chem., 100, 5715-5720.
6. Shurki, A., Hiberty, P.C., and Shaik, S. (1999) J. Am. Chem. Soc., 121, 822-834.
7. Galbraith, J.M., Blank, E., Shaik, S., and Hiberty, P.C. (2000) Chem. Eur. J., 6, 2425-2434.
8. Lauvergnat, D. and Hiberty, P.C. (1995) J. Mol. Struct. THEOCHEM, 338, 283-291.
9. Shaik, S., Danovich, D., Silvi, B., Lauvergnat, D., and Hiberty, P.C. (2005) Chem. Eur. J., 11, 6358-6371.
10. Zhang, L., Ying, F., Wu, W., Hiberty, P.C., and Shaik, S. (2009) Chem. Eur. J., 15, 2979-2989.
11. Wu, W., Gu, J., Song, J., Shaik, S., and Hiberty, P.C. (2009) Angew. Chem. Int. Ed., 48, 1407-1410.
12. Shaik, S., Danovich, D., Wu, W., and Hiberty, P.C. (2009) Nat. Chem., 1, 443-449.
13. Shaik, S., Chen, Z., Wu, W., Stanger, A., Danovich, D., and Hiberty, P.C. (2009) ChemPhysChem, 10, 2658-2669.
14. Silvi, B. and Savin, A. (1994) Nature, 371, 683-686.
15. Bader, R.F.W. (1990) Atoms in Molecules:A Quantum Theory, Oxford University Press, Oxford.
16. Shaik, S. and Hiberty, P.C. (2008) A Chemist's Guide to Valence Bond Theory, Chapter 3, 9, 10, John Wiley & Sons Inc., Hoboken, NJ.
17. Wu, W., Su, P., Shaik, S., and Hiberty, P.C. (2011) Chem. Rev., 111, 7557-7593.
18. Lewis, G.N. (1916) J. Am. Chem. Soc., 38, 762-785.
19. Servos, J.W. (1990) Physical Chemistry from Ostwald to Pauling, Princeton University Press, Princeton, NJ, pp. 4-5, 135.
20. Langmuir, I. (1919) J. Am. Chem. Soc., 41, 868-934.
21. Jensen, W.B. (1984) J. Chem. Educ., 61, 191-200.
22. Davenport, D.A. (1996) Bull. Hist. Chem., 19, 13-18.
23. Calvin, M. (1984) J. Chem. Educ., 61, 14-18.
24. Nye, M.J. (1993) From Chemical Philosophy to Theoretical Chemistry, University of California Press, Los Angeles, CA, p. 186.
25. Heitler, W. and London, F. (1927) Z. Phys., 44, 455-472.
26. English Translation Hettema, H. (2000) Quantum Chemistry Classic Scientific Paper, World Scientific, Singapore, pp. 140-155.
27. London, F. (1928) Z. Phys., 46, 455-477.
28. Saltzman, M.D. (1996) Bull. Hist. Chem., 19, 25-32.
29. Pauling, L. (1939) The Nature of the Chemical Bond, 3rd edn, 1960, Cornell University Press, Ithaca, New York.
30. Slater, J.C. (1965) J. Chem. Phys., 43, S11-S17.
31. van Vleck, J.H. and Sherman, A. (1935) Rev. Mod. Phys., 7, 167-228.
32. Servos, J.W. (1984) J. Chem. Educ., 61, 5-10.
33. Gavroglu, K. and Simoes, A. (1994) Stud. Biol. Phys. Sci., 25, 47-110.
34. Hager, T. (1995) Force of Nature: The Life of Linus Pauling, Simon and Schuster, New York, pp. 62-63.
35. Sanderson, R.T. (1983) Polar Covalence, Academic Press, New York.
36. For pioneering localization methods, see: (a) Edmiston, C. and Ruedenberg, K. (1963) Rev. Mod. Phys., 35, 457-464.
37. Rutledge, R.M. and Saturno, A.F. (1965) J. Chem. Phys., 43, 597-602.
38. Boys, S.F. (1960) Rev. Mod. Phys., 32, 296-299.
39. Foster, J.M. and Boys, S.F. (1960) Rev. Mod. Phys., 32, 300-302.
40. Weinhold, F. and Landis, C.R. (2005) Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Chembrige Univeristy Press, Chembridge.
41. Weinhold, F. and Landis, C.R. (2012) Discovering Chemistry with Natural Bond Orbitals, John Wiley & Sons Inc., Hoboken, NJ.
42. Silvi, B. (2005) Chem. Eur. J., 11, 6358-6371; AIM analysis, of SiH3-F and Li-F using B3LYP/6-31+G* and B3LYP/6-31G* levels cited in Ref. 3g above.
43. Bader, R.F.W. and Nguyen-Dang, T.T. (1981) Adv. Quantum Chem., 14, 63-124.
44. For other highly ionic bonds to silicon, see: Henn, J., Ilge, D., Leusser, D., Stalke, D., and Engles, D. (2004) J. Phys. Chem. A, 108, 9442-9452.
45. Apeloig, Y. (1989) in The Chemistry of Organic Silicon Compounds, Vol. 1, Chapter 2 (eds Y. Apeloig and Z. Rappoport), John Wiley & Sons, Ltd, Chichester.
46. For a variety of crystalized carbocationic salts, see: Laube, T. (1995) Acc. Chem. Res., 28, 399-405.
47. Gomes de Mesquita, A.H., MacGillavry, C.H., and Eriks, K. (1965) Acta Crystallogr., 18, 437-443.
48. Prakash, G.K.S., Keyaniyan, S., Aniszfeld, S.K.R., Heiliger, L., Olah, G.A., Stevens, R.C., Choi, H.-K., and Bau, R. (1987) J. Am. Chem. Soc., 109, 5123-5126.
49. For a recent ''bottling'' of tert-Butyl cation, see: Kato, T. and Reed, A. (2004) Angew. Chem. Int. Ed., 43, 2908-2911.
50. For a few reviews on the elusive R3Si+ cation in condense phases, see:Apeloig, Y. and Stanger, A. (1987) J. Am. Chem. Soc., 109, 272-273.
51. Lambert, J.B., Kania, L., and Zhang, S. (1995) Chem. Rev., 95, 1191-1201.
52. For a recent exception, see: Lambert, J.B. and Zhao, Y. (1997) Angew. Chem., Int. Ed. Engl., 36, 400-401.
53. Kim, K.-C., Reed, C.A., Elliott, D.W., Mueller, L.J., Tham, F., Lin, L., and Lambert, J.B. (2002) Science, 297, 825-827.
54. See also, Cremer, D. and Kraka, E. (1984) Angew. Chem., Int. Ed. Engl., 23, 627-628.
55. Low, A.A. and Hall, M.B. (1990) in Theoretical Models of Chemical Bonding, Part 2 (ed. Z.B. Maksic), Springer-Verlag, New York, pp. 544-591.
56. Schwarz, W.H.E., Valtazanos, P., and Ruedenberg, K. (1985) Theor. Chim. Acta, 68, 471-506.
57. Lusar, R., Beltrán, A., Andrés, J., Noury, S., and Silvi, B. (1999) J. Comput. Chem., 20, 1517-1526.
58. Silvi, B. (2003) J. Phys. Chem. A, 107, 3081-3085.
59. Kraka, E. and Cremer, D. (1990) in Theoretical Models of Chemical Bonding, Part 2 (ed. Z.B. Maksic), Springer-Verlag, New York, pp. 457-543.
60. Coppens, P. (2005) Angew. Chem. Int. Ed., 44, 6810-6811.
61. Coppens, P. (1997) X-ray Densities and Chemical Bonding, Oxford University Press, New York.
62. Messershmidt, M., Scheins, S., Grubert, L., Patzel, M., Szeimies, G., Paulmann, C., and Luger, P. (2005) Angew. Chem. Int. Ed., 44, 3925-3928.
63. Polo, V., Andres, J., and Silvi, B. (2007) J. Comput. Chem., 28, 857-864.
64. For ''dynamic ionicity'', see: Maynau, D. and Malrieu, J.-P. (1988) J. Chem. Phys., 88, 3163-3173.
65. Rincon, L. and Almeida, R. (1998) J. Phys. Chem. A, 102, 9244-9254.
66. Kitaura, K. and Morokuma, K. (1976) Int. J. Quantum Chem., 10, 325-340.
67. Ziegler, T. and Rauk, A. (1977) Theor. Chim. Acta, 46, 1-10.
68. Velde, G.T., Bickelhaupt, F.M., Baerends, E.J., van Gisbergen, S.J.A., Fonseca Guerra, C., Snijders, J.G., and Ziegler, T. (2001) J. Comput. Chem., 22, 931-967.
69. Krapp, A., Bickelhaupt, F.M., and Frenking, G. (2006) Chem. Eur. J., 12, 9196-9216.
70. Hiberty, P.C., Ramozzi, R., Song, L., Wu, W., and Shaik, S. (2006) Faraday Discuss., 135, 261-272.
71. Kutzelnigg, W. (1990) in Theoretical Models of Chemical Bonding, Part 2 (ed. Z.B. Maksic), Springer-Verlag, New York, pp. 1-44.
72. Ruedenberg, K. (1962) Rev. Mod. Phys., 34, 326-376.
73. Feinberg, M.J. and Ruedenberg, K. (1971) J. Chem. Phys., 54, 1495-1591.
74. Wilson, C.Q. and Goddard, W.A. III, (1972) Theor. Chim. Acta, 26, 195-210.
75. Rozendaal, A. and Baerends, E.J. (1985) Chem. Phys., 95, 57-91.
76. Ruedenberg, K. and Schmidt, M. (2007) J. Comput. Chem., 28, 391-410.
77. Bickelhaupt, F.M. and Baerends, E.J. (2000) Rev. Comput. Chem., 15, 1-86.
78. Shaik, S.S. (1989) in New Theoretical Concepts for Understanding Organic Reactions, NATO ASI Series C267 (eds J. Bertran and G.I. Csizmadia), Kluwer Publisher, Dordrecht, pp. 165-217.
79. Ploshnik, E., Danovich, D., Hiberty, P.C., and Shaik, S. (2011) J. Chem. Theor. Comput., 7, 955-968.
80. Su, P., Song, L., Wu, W., Shaik, S., and Hiberty, P.C. (2008) J. Phys. Chem. A, 112, 2988-2997.
81. Hiberty, P.C., Danovich, D., Shurki, A., and Shaik, S. (1995) J. Am. Chem. Soc., 117, 7760-7768.
82. Messerschmidt, M., Wagner, A., Wong, M.W., and Luger, P. (2002) J. Am. Chem. Soc., 124, 732-733.
83. Platts, J.A., Overgaard, J., Jones, C., Iversen, B.B., and Stasch, A. (2011) J. Phys. Chem. A, 115, 194-200.
84. Dunitz, J.D. and Seiler, P. (1983) J. Am. Chem. Soc., 105, 7056-7058.
85. Dunitz, J.D., Schweizer, W.B., and Seiler, P. (1983) Helv. Chem. Acta, 66, 123-133.
86. Coppens, P., Yang, Y.W., Blessing, R.H., Cooper, W.F., and Larsen, F.K. (1977) J. Am. Chem. Soc., 99, 760-766.
87. Savariault, J.-M. and Lehmann, M.S. (1980) J. Am. Chem. Soc., 102, 1298-1303.
88. Ruedenberg, K. and Schwarz, W.H.E. (1990) J. Chem. Phys., 92, 4956-4969.
89. Generally, a better reference state can be made from deformed rather than spherical atoms. See, Schwarz, W.H.E., Ruedenberg, K., and Mensching, L. (1989) J. Am. Chem. Soc., 111, 6926-6941.
90. Hiberty, P.C., Megret, C., Song, L., Wu, W., and Shaik, S. (2006) J. Am. Chem. Soc., 128, 2836-2843.
91. O'Neal, S.V., Schaefer, H.F. III, and Bender, C.F. (1974) Proc. Natl. Acad. Sci. U.S.A., 71, 104-106.
92. Dunning, T.H. Jr., (1984) J. Phys. Chem., 88, 2469-2477.
93. Bender, C.F., Garrison, B.J., and Schaefer, H.F. III, (1975) J. Chem. Phys., 62, 1188-1190.
94. Voter, A.F. and Goddard, W.A. III, (1981) J. Chem. Phys., 75, 3638-3639.
95. Dobbs, K.D. and Dixon, C.A. (1993) J. Phys. Chem., 97, 2085-2091.
96. Bartoszek, F.E., Manos, D.M., and Polanyi, J.C. (1978) J. Chem. Phys., 69, 933-935.
97. Shaik, S. and Hiberty, P.C. (2004) Rev. Comput. Chem., 20, 1-100.
98. Fiorillo, A.A. and Galbraith, J.M. (2004) J. Phys. Chem. A, 108, 5126-5130.
99. Coote, M.L., Pross, A., and Radom, L. (2003) Org. Lett., 5, 4689-4692.
100. Galbraith, J.M., Shurki, A., and Shaik, S. (2000) J. Phys. Chem., 104, 1262-1270.
101. Hiberty, P.C., Humbel, S., Danovich, D., and Shaik, S. (1995) J. Am. Chem. Soc., 117, 9003-9011.
102. Hiberty, P.C., Humbel, S., and Archirel, P. (1994) J. Phys. Chem., 98, 11697-11704.
103. Wu, W. and Shaik, S. (1999) Chem. Phys. Lett., 301, 37-42.
104. Shaik, S. and Shurki, A. (1999) Angew. Chem. In. Ed., 38, 586-625.
105. 3 bond energy change due to methyl cation attachment to the nitrogen atom, see, Shaik, S.S. (1991) in An Encomium to Linus Pauling. Molecules in Natural Science and Medicine (eds Z.B. Maksic and M.E. Maksic), Ellis Horwood, London, 12.
106. Braida, B. and Hiberty, P.C. (2013) Nat. Chem., 5, 417-422.
107. Kost, D. and Kalikhman, I. (2009) Acc. Chem. Res., 42, 303-314.
108. Dávalos, J.Z., Herrero, R., Abboud, J.-L.M., Mó, O., and Yáñez, M. (2007) Angew. Chem. Int. Ed., 46, 381-385.
109. Panisch, R., Bolte, M., and Müller, T. (2006) J. Am. Chem. Soc., 128, 9676-9682.
110. Lühmann, N., Panisch, R., Hirao, H., Shaik, S., and Müller, T. (2011) Organometallics, 30, 4087-4096.
111. Llusar, R., Beltran, A., Andrés, J., Fuster, F., and Silvi, B. (2001) J. Phys. Chem. A, 105, 9460-9466.
112. Cho, K.B., Carvajal, M.A., and Shaik, S. (2009) J. Phys. Chem. B, 113, 336-346.
113. Grochala, W., Hoffmann, R., Feng, J., and Ashcroft, N.W. (2007) Angew. Chem. Int. Ed., 46, 3620-3642.
114. Dognon, J.-P., Clavaguéra, C., and Pyykkö, P. (2009) J. Am. Chem. Soc., 131, 238-243.
115. Rupar, P., Staroverov, V.N., and Baines, K.M. (2008) Science, 322, 1360-1363.
116. Gershoni-Porrane, R. and Stanger, A. (2012) Chem. Phys. Chem., 13, 2377-2381.
117. Goddard, W.A. III, Dunning, T.H., Hunt, W.J., and Hay, P.J. (1973) Acc. Chem. Res., 6, 368-376.
118. Goodgame, M.M. and Goddard, W.A. III, (1985) Phys. Rev. Lett., 54, 661-664.
119. Cooper, D.L., Gerratt, J., and Raimondi, M. (1991) Chem. Rev., 91, 929-964.
120. Sironi, M., Raimondi, M., Martinazzo, R., and Gianturco, F.A. (2002) in Valence Bond Theory (ed. D.L. Cooper), Elsevier, Amsterdam, pp. 261-277.
121. For VBSCF, see: (a) Verbeek, J. and van Lenthe, J.H. (1991) J. Mol. Struct. (THEOCHEM), 229, 115-137.
122. van Lenthe, J.H., Dijkstra, F., and Havenith, W.A. (2002) in Valence Bond Theory (ed. D.L. Cooper), Elsevier, Amsterdam, pp. 79-116.
123. For the leading BOVB references, see:(a) Hiberty, P.C., Flament, J.P., and Noizet, E. (1992) Chem. Phys. Lett., 189, 259-265.
124. Hiberty, P.C. (1997) in Modern Electronic Structure Theory and Applications in Organic Chemistry (ed. E.R. Davidson), World Scientific, River Edge, NY, pp. 289-367.
125. Hiberty, P.C. and Shaik, S. (2002) Theor. Chem. Acc., 108, 255-275.
126. For leading VBCI references, see: (a) Wu, W., Song, L., Cao, Z., Zhang, Q., and Shaik, S. (2002) J. Phys. Chem. A, 106, 2721-2726.
127. Song, L., Wu, W., Zhang, Q., and Shaik, S. (2004) J. Comput. Chem., 25, 472-478.