Observations and descriptions versus explanations-an example: Does nature, does theory know about steric hindrance?

Chemistry - A European Journal

Volumn 18, Issue 15, 2012, Pages 4470-4479

  Schwarz, W H Eugen ^a,b   Schmidbaur, Hubert ^c,d  

^a TSINGHUA UNIVERSITY   (China)

^b UNIVERSITY OF SIEGEN   (Germany)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^d KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

chemical bonding; chemical concepts; computational chemistry; nucleophilic substitution; steric hindrance

Indexed keywords

CHEMICAL BONDINGS; CHEMICAL CONCEPTS; CHEMICAL PHENOMENAS; CHEMICAL THEORIES; FINAL STATE; FOUR-POINT; INTERMEDIATE STATE; NONSTATIONARY; NUCLEOPHILIC SUBSTITUTION; QUANTUM CHEMICAL INVESTIGATION; RELAXATION MECHANISM; STERIC HINDRANCES; STERIC REPULSIONS;

CHEMICAL BONDS; COMPUTATIONAL CHEMISTRY; QUANTUM CHEMISTRY;

CHEMICAL REACTIONS;

EID: 84859320383     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102687     Document Type: Review

References (126)

1. I. Fernández, G. Frenking, E. Uggerud, Chem. Eur. J. 2009, 15, 2166.
2. W. J. van Zeist, F. M. Bickelhaupt, Chem. Eur. J. 2010, 16, 5538.
3. I. Fernandez, G. Frenking, E. Uggerud, Chem. Eur. J. 2010, 16, 5542.
4. R. F. W. Bader, J. Phys. Chem. A 2009, 113, 10391
5. R. F. W. Bader, J. Phys. Chem. A 2010, 114, 7431
6. R. F. W. Bader, Chem. Eur. J. 2006, 12, 2896
7. R. F. W. Bader, Found. Chem. 2011, 13, 11-37.
8. L. Gmelin, Handbuch der theoretischen Chemie, Varrentrapp, Frankfurt-Main, 1817.
9. F. Bacon, Novum Organon, John Bill, London, 1620
10. I. Newton, Opticks, 4th ed., Book 3-The Queries, William Innys, London, 1730.
11. D. Bernoulli, Hydrodynamica, Dulsecker, Strassburg, 1738
12. J. Dalton, A New System of Chemical Philosophy, Russell, Manchester, 1808
13. R. J. E. Clausius, Verh. Königl. Preuß. Akad. Wiss. Berlin, 1850, 42
14. R. J. E. Clausius, Annalen der Physik 1857, 100, 353
15. J. C. Maxwell, Theory of Heat, Longmans and Green, London, 1871
16. L. Boltzmann, Vorlesungen über Gastheorie, J. A. Barth, Leipzig, 1896.
17. L. Pauling, E. B. Wilson, Introduction to quantum mechanics, McGraw-Hill, New York, 1935
18. H. Hellmann, Einführung in die Quantenchemie, Deuticke, Leipzig, 1937
19. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca, NY, 1939
20. H. Eyring, J. E. Walter, G. E. Kimball, Quantum Chemistry, Wiley, New York, 1944.
21. A. F. Hollemann, Lehrbuch der Chemie, Veit, Leipzig, 1898 -1900
22. H. Remy, Lehrbuch der anorganischen Chemie, Geest & Portig, Leipzig, 1936
23. T. L. Brown, H. E. LeMay, B. E. Bursten, Chemistry: The Central Science, Prentice Hall, Englewood Cliffs, NJ, 1991
24. C. E. Housecroft, E. C. Constable, Chemistry, Pearson, London, 1997.
25. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, NY, 1953
26. R. G. Pearson, F. Basolo, Mechanisms of Inorganic Reactions, Wiley, New York, 1958
27. R. J. Gillespie, Molecular geometry, Nostrand Reinhold, London, 1972.
28. E. Hückel, Z. Elektrochem. Angew. Phys. Chem. 1937, 43, 827
29. A. Streiwieser, Molecular Orbital Theory for Organic Chemists, Wiley, New York, 1961
30. R. Hoffmann, Solids and Surfaces, VCH, Weinheim, 1988.
31. K. Ruedenberg, Rev. Mod. Phys. 1962, 34, 326
32. T. Bitter, K. Ruedenberg, W. H. E. Schwarz, J. Comput. Chem. 2007, 28, 411.
33. T. Bitter, S. G. Wang, K. Ruedenberg, W. H. E. Schwarz, Theor. Chem. Acc. 2010, 127, 237.
34. V. Pophristic, L. Goodman, Nature 2001, 411, 565
35. F. Weinhold, Angew. Chem. 2003, 115, 4320
36. Angew. Chem. Int. Ed. 2003, 42, 4188
37. P. R. Schreiner, Angew. Chem. 2002, 114, 3729
38. Angew. Chem. Int. Ed. 2002, 41, 3579.
39. N2 Reaction, Wiley, New York, 1992.
40. K. J. Morokuma, Chem. Phys. 1971, 55, 1236
41. K. Kitaura, K. Morokuma, Int. J. Quantum Chem. 1976, 10, 325
42. T. Ziegler, A. Rauk, Theor. Chim. Acta 1977, 46, 1
43. T. Ziegler, A. Rauk, Inorg. Chem. 1979, 18, 1755
44. T. Ziegler, A. Rauk, E. J. Baerends, Theor. Chim. Acta 1977, 43, 261
45. F. M. Bickelhaupt, E. J. Baerends, Rev. Comput. Chem. 2000, 15, 1
46. F. M. Bickelhaupt, J. Comput. Chem. 1999, 20, 114-128
47. T. Ziegler, V. Tschinke, A. Becke, J. Am. Chem. Soc. 1987, 109, 1351
48. J. Li, G. Schreckenbach, T. Ziegler, J. Am. Chem. Soc. 1995, 117, 486.
49. N. Graulich, H. Hopf, P. R. Schreiner, Chem. Soc. Rev. 2010, 39, 1503. "Heuristic thinking makes a chemist smart".
50. M. von Hopffgarten, G. Frenking, Chem. Eur. J. 2008, 14, 10227
51. A. Krapp, G. Frenking, Chem. Eur. J. 2007, 13, 8256.
52. R. F. W. Bader, Chem. Eur. J. 2006, 12, 2896
53. R. F. W. Bader, D. C. Fang, J. Chem. Theory Comput. 2005, 1, 403
54. R. F. W. Bader, Adv. Quantum Chem. 2009, 57, 285.
55. J. Poater, M. Solá, F. M. Bickelhaupt, Chem. Eur. J. 2006, 12, 2889-2895, 2902-2905
56. J. Poater, R. Visser, M. Solá, F. M. Bickelhaupt, J. Org. Chem. 2007, 72, 1134-1142
57. M. A. van Bochove, M. Swart, F. M. Bickelhaupt, J. Am. Chem. Soc. 2006, 128, 10738-10744
58. A. P. Bento, F. M. Bickelhaupt, J. Org. Chem. 2007, 72, 2201-2207.
59. S. G. Wang, Y. X. Qiu, W. H. E. Schwarz, Chem. Eur. J. 2010, 16, 9107-9116
60. S. G. Wang, Y. X. Qiu, W. H. E. Schwarz, Chem. Eur. J. 2009, 15, 6032-6040.
61. Q. Wu, P. W. Ayers, Y. K. Zhang, J. Chem. Phys. 2009, 131, 164112.
62. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
63. J. Meister, W. H. E. Schwarz, J. Phys. Chem. 1994, 98, 8245-8252.
64. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Clarendon, Oxford, 1990.
65. A. D. McNaught, A. Wilkinson, IUPAC Compendium of Chemical Terminology, 2nd ed., IUPAC, Research Triangle Park, 1997; http://old.iupac.org/publications/ compendium/index.html.
66. C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2 nd ed., Cornell University Press, Ithaca, NY, 1969
67. T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper Collins, New York, 1987
68. N. R. H. Crabtree, The Organometallic Chemistry of the Transition Metals, Wiley, Hoboken, NJ, 2005
69. E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, CA, 2006
70. H. J. Butt, K. Graf, M. Kappl, Physics and chemistry of interfaces, Wiley-VCH, Weinheim, 2008
71. V. M. Rotello, S. Thayumanavan, Molecular recognition and polymers-control of polymer structure and self-assembly, Wiley, Hoboken, NJ, 2008
72. L. Allinger, Molecular structure-understanding steric and electronic effects from molecular mechanics, Wiley, Hoboken, NJ, 2010.
73. W. Kutzelnigg, Angew. Chem. 1973, 85, 551-568
74. Angew. Chem. Int. Ed. Engl. 1973, 12, 546-562.
75. K. Ruedenberg, M. W. Schmidt, J. Phys. Chem. A 2009, 113, 1954-1968.
76. J. Neus, Aromatizität-Geschichte und mathematische Analyse eines fundamentalen chemischen Begriffs, HYLE Publications, Karlsruhe, 2002.
77. L. Fleck, The Genesis and Development of a Scientific Fact, (Eds.:, T. J. Trenn, T. K. Merton,), University of Chicago Press, Chicago, 1979.
78. W. H. E. Schwarz, J. Chem. Educ. 2010, 87, 444-448
79. S. G. Wang, W. H. E. Schwarz, Angew. Chem. 2009, 121, 3456-3467
80. Angew. Chem. Int. Ed. 2009, 48, 3404-3415.
81. A. B. Laffer, http://www.heritage.org/Research/Reports/2004/06/The- Laffer-Curve-Past-Present-and-Future. http://en.wikipedia.org/wiki/Laffer-curve.
82. R. Knippenhahn, A. Weigert, Stellar Structure and Evolution, Springer, Berlin, 1991
83. G. Shaviv, The Life of Stars, Springer, Heidelberg, 2009.
84. H. Hellmann, Einführung in die Quantenchemie, Deuticke, Vienna, 1937
85. R. P. Feynman, Phys. Rev. 1939, 56, 340-343.
86. J. Autschbach, W. H. E. Schwarz, J. Phys. Chem. A 2000, 104, 6039-6046.
87. S. T. Epstein, Variation Method in Quantum Chemistry, Academic Press, New York, 1974.
88. P. Pulay, Mol. Phys. 1969, 17, 197-204.
89. P. I. Dema'yanov, P. M. Polestshuk, Chem. Eur. J. 2012, DOI
90. I. F. Shishkov, V. A. Sipachev, P. I. Dema'yanov, O. V. Dorofeeva, N. Vogt, Y. V. Vishnevskiy, L. V. Vilkov, J. Mol. Struct. 2010, 978, 41-47
91. P. I. Dema'yanov, P. M. Poleshchuk, I. P. Gloriozov, A. Y. Vasil'kov, Russ. J. Phys. Chem. A 2010, 114, 1731-1744.
92. H. Silberbach, J. Chem. Phys. 1991, 94, 2977-2985.
93. H. Schmidbaur, Angew. Chem. 1983, 95, 980-1000
94. Angew. Chem. Int. Ed. Engl. 1983, 22, 907-927
95. O. I. Kolodiazhnyi, Tetrahedron 1996, 52, 1855-1929
96. R. Tonner, F. Axler, B. Neumüller, W. Petz, G. Frenking, Angew. Chem. 2006, 118, 8206-8211
97. Angew. Chem. Int. Ed. 2006, 45, 8038-8042
98. R. Tonner, G. Heydenrych, G. Frenking, ChemPhysChem 2008, 9, 1474-1481. See also the references listed in
99. N. Takagi, G. Frenking, Theor. Chem. Acc. 2011, 129, 615-623.
100. P. Hohenberg, W. Kohn, Phys. Rev. B 1964, 136, 864-871.
101. G. Frenking, K. Wichmann, N. Fröhlich, J. Grobe, W. Golla, D. Le Van, B. Krebs, M. Läge, Organometallics 2002, 21, 2921-2930
102. I. Fernández, G. Frenking, E. Uggerud, J. Org. Chem. 2010, 75, 2971-2980.
103. C. Fonseca Guerra, F. M. Bickelhaupt, Angew. Chem. 1999, 111, 3120-3122
104. Angew. Chem. Int. Ed. 1999, 38, 2942-2945
105. C. Fonseca Guerra, F. M. Bickelhaupt, J. G. Snijders, E. J. Baerends, Chem. Eur. J. 1999, 5, 3581-3594
106. C. Fonseca Guerra, T. van der Wijst, F. M. Bickelhaupt, Chem. Eur. J. 2006, 12, 3032-3042
107. C. Fonseca Guerra, Z. Szekeres, F. M. Bickelhaupt, Chem. Eur. J. 2011, 17, 8816-8818.
108. X. Chen, C. K. Regan, S. L. Craig, E. H. Krenske, K. N. Houk, W. L. Jorgensen, J. I. Brauman, J. Am. Chem. Soc. 2009, 131, 16162-16170.
109. R. Hoffmann, J. Mol. Struct. 1998, 440-473, 1-6
110. S. Alvarez, R. Hoffman, C. Mealli, Chem. Eur. J. 2009, 15, 8358-8373.
111. B. T. Sutcliffe, Int. J. Quantum Chem. 1996, 58, 645-655.
112. S. Shahbazian, M. Zahedi, Found. Chem. 2006, 8, 37-52
113. S. Shahbazian, M. Zahedi, Found. Chem. 2007, 9, 85-95.
114. J. G. Snijders, P. Pyykkö, Chem. Phys. Lett. 1980, 75, 5-8
115. P. Pyykkö, J. G. Snijders, E. J. Baerends, Chem. Phys. Lett. 1981, 83, 432-437. But
116. W. H. E. Schwarz, Phys. Scr. 1987, 36, 403-411.
117. M. Levy, Proc. Natl. Acad. Sci. USA 1979, 76, 6062-6065
118. M. Levy, Int. J. Quantum Chem. 2010, 110, 3140-3144.
119. R. Tonner, G. Frenking, M. Lein, P. Schwerdtfeger, ChemPhysChem 2011, 12, 2081-2084.
120. P. Seiler, J. D. Dunitz, Helv. Chim. Acta 1986, 69, 1107-1112.
121. D. T. Campbell, in Scientific Methodology in the Study of Mind: evolutionary epistemology (Eds.:, E. Tobach, G. Greenberg,), Erlbaum, Hillsdale NJ, 1990, p. 1-17
122. R. F. Henry, Stud. Hist. Philos. Mod. Phys. 2010, 41, 183-191
123. R. F. Henry, in Philosophy of Chemistry: A Synthesis of a New Discipline (Eds.:, D. Baird, E. R. Scerri, L. McIntyre,), Springer, Heidelberg, 2006, p. 173-189
124. The internal electronic kinetic energy is related to the quantum potential given by D. Bohm (, D. Bohm, Phys. Rev. 1952, 85, 166-179, and
125. D. Bohm, Phys. Rev. 1952, 85, 180-193); see
126. S. Esposito, arXiv:quantph/990201v1