Electron flow in reaction mechanisms - Revealed from first principles

Angewandte Chemie - International Edition

Volumn 54, Issue 18, 2015, Pages 5518-5522

  Knizia, Gerald ^a,b   Klein, Johannes E M N ^a,c  

^a UNIVERSITY OF STUTTGART   (Germany)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF MINNESOTA   (United States)

Author keywords

ab initio calculations; bond theory; quantum chemistry; reaction mechanisms

Indexed keywords

CALCULATIONS;

AB INITIO CALCULATIONS; AB INITIO COMPUTATIONS; BOND REARRANGEMENT; BOND THEORY; FIRST PRINCIPLES; PHYSICAL REALITY; REACTION COORDINATES; REACTION MECHANISM;

QUANTUM CHEMISTRY;

EID: 85027920707     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410637     Document Type: Article

References (52)

1. W. O. Kermack, R. Robinson, J. Chem. Soc. Trans. 1922, 121, 427-440.
2. C. K. Ingold, Chem. Rev. 1934, 15, 225-274.
3. N. Epiotis, J. Mol. Struct.: THEOCHEM 1991, 229, 205-217.
4. H. Hosoya, J. Mol. Struct.: THEOCHEM 1999, 461, 473-482.
5. V. Gineitytė, Lit. J. Phys. 2011, 51, 107-126.
6. H. B. Schlegel, WIREs Comput. Mol. Sci. 2011, 1, 790-809
7. D. Sheppard, R. Terrell, G. Henkelman, J. Chem. Phys. 2008, 128, 134106
8. D. J. Wales, Int. Rev. Phys. Chem. 2006, 25, 237-282.
9. J. Keeler, P. Wothers, Chemical structure and reactivity: an integrated approach, Oxford University Press, Oxford, 2013.
10. S. M. Bachrach, Computational organic chemistry, Wiley, Hoboken, 2014.
11. K. Fukui, T. Yonezawa, H. Shingu, J. Chem. Phys. 1952, 20, 722-725
12. K. Fukui, Science 1982, 218, 747-754
13. R. B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 1965, 87, 395-397
14. R. Hoffmann, Angew. Chem. Int. Ed. Engl. 1982, 21, 711-724
15. Angew. Chem. 1982, 94, 725-739.
16. Z. Konkoli, E. Kraka, D. Cremer, J. Phys. Chem. A 1997, 101, 1742-1757
17. D. Cremer, E. Kraka, Curr. Org. Chem. 2010, 14, 1524-1560
18. E. Kraka, D. Cremer, Acc. Chem. Res. 2010, 43, 591-601
19. E. Kraka, H. Joo, D. Cremer, Mol. Phys. 2010, 108, 2667-2685.
20. V. Polo, J. Andres, S. Berski, L. R. Domingo, B. Silvi, J. Phys. Chem. A 2008, 112, 7128-7136
21. X. Li, Y. Zeng, L. Meng, S. Zheng, J. Phys. Chem. A 2007, 111, 1530-1535
22. J. Andrés, S. Berski, J. Contreras-García, P. González-Navarrete, J. Phys. Chem. A 2014, 118, 1663-1672.
23. J. E. M. N. Klein, G. Knizia, B. Miehlich, J. Kästner, B. Plietker, Chem. Eur. J. 2014, 20, 7254-7257.
24. G. Knizia, J. Chem. Theory Comput. 2013, 9, 4834-4843.
25. J. Pipek, P. G. Mezey, J. Chem. Phys. 1989, 90, 4916-4926.
26. J. M. Foster, S. F. Boys, Rev. Mod. Phys. 1960, 32, 300-302.
27. C. Edmiston, K. Ruedenberg, Rev. Mod. Phys. 1963, 35, 457-464.
28. T. Janowski, J. Chem. Theory Comput. 2014, 10, 3085-3091.
29. S. Lehtola, H. Jõnsson, J. Chem. Theory Comput. 2014, 10, 642-649.
30. A. C. West, M. W. Schmidt, M. S. Gordon, K. Ruedenberg, J. Chem. Phys. 2013, 139, 234107.
31. K. Ruedenberg, M. W. Schmidt, M. M. Gilbert, Chem. Phys. 1982, 71, 51-64.
32. W. C. Lu, C. Z. Wang, M. W. Schmidt, L. Bytautas, K. M. Ho, K. Ruedenberg, J. Chem. Phys. 2004, 120, 2629-2637.
33. A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735
34. J. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211-7218
35. A. E. Reed, F. Weinhold, J. Chem. Phys. 1985, 83, 1736-1740
36. E. D. Glendening, C. R. Landis, F. Weinhold, WIREs Comput. Mol. Sci. 2012, 2, 1-42.
37. F. Weinhold, Discovering chemistry with natural bond orbitals, Wiley, Hoboken, 2012, chap. 10.
38. E. D. Glendening, F. Weinhold, J. Comput. Chem. 1998, 19, 593-609.
39. S. Shaik, P. C. Hiberty, WIREs Comput. Mol. Sci. 2011, 1, 18-29.
40. R. F. Bader, Atoms in molecules: A quantum theory, Oxford University Press, Oxford, 1994.
41. D. Y. Zubarev, A. I. Boldyrev, Phys. Chem. Chem. Phys. 2008, 10, 5207-5217.
42. S. Shaik, W. Lai, H. Chen, Y. Wang, Acc. Chem. Res. 2010, 43, 1154-1165.
43. F. Weinhold, R. A. Klein, Chem. Educ. Res. Pract. 2014, 15, 276-285.
44. We have been informed that bond transformations can also be visualized using NRT, through weighted mixtures of NLMOs from participating NRT resonance structures [E. D. Glendening, personal communication]. See http://nbo6.chem.wisc.edu/ispring-ppt/index.html (accessed 17.07.2014).
45. D. Andrae, I. Barth, T. Bredtmann, H.-C. Hege, J. Manz, F. Marquardt, B. Paulus, J. Phys. Chem. B 2011, 115, 5476-5483.
46. K. Fukui, J. Phys. Chem. 1970, 74, 4161-4163.
47. T. Haven, G. Kubik, S. Haubenreisser, M. Niggemann, Angew. Chem. Int. Ed. 2013, 52, 4016-4019
48. Angew. Chem. 2013, 125, 4108-4111.
49. H. Joo, E. Kraka, W. Quapp, D. Cremer, Mol. Phys. 2007, 105, 2697-2717.
50. J. E. M. N. Klein, B. Miehlich, M. S. Holzwarth, M. Bauer, M. Milek, M. M. Khusniyarov, G. Knizia, H.-J. Werner, B. Plietker, Angew. Chem. Int. Ed. 2014, 53, 1790-1794
51. Angew. Chem. 2014, 126, 1820-1824.
52. G. Knizia, IboView; see http://www.iboview.org.