Ab Initio Calculations of Charge Distributions in Monosubstituted Benzenes and in Meta- and Para-Substituted Fluorobenzenes. Comparison with 1H, 13C, and 19F Nmr Substituent Shifts

Progress in Physical Organic Chemistry

Volumn 12, Issue , 2007, Pages 159-187

  Hehre, W J ^a   Taft, R W ^a   Topsom, R D ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LA TROBE UNIVERSITY   (Australia)

Author keywords

Charge distributions; Electron populations; Magnetic resonance shifts; Para carbon atoms; Substituent constants

Indexed keywords

CHARGE DISTRIBUTION; MAGNETIC RESONANCE;

19F NMR; AB INITIO CALCULATIONS; CARBON ATOMS; ELECTRON POPULATION; MONOSUBSTITUTED BENZENES; SUBSTITUENT CONSTANTS;

CALCULATIONS;

EID: 84986598785     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470171912.ch6     Document Type: Chapter

References (55)

1. See, for example, A. Streitweiser, Jr., Molecular Orbital Theory for Organic Chemists.Wiley, New York, 1961.
2. J. E. Bloor and D. L. Breen, J. Phys. Chem. 72, 716, (1968).
3. R. T. C. Brownlee and R. W. Taft, J. Amer. Chem. Soc. 92, 7007, (1970).
4. W. J. Hehre, L. Radom, and J. Pople, J. Amer. Chem. Soc. 94, 1496, (1972).
5. G. A. Olah and D. A. Forsyth, J. Amer. Chem. Soc. 97, 3137, (1975).
6. G. K. Hamer, I. R. Peat, and W. F. Reynolds, Can. J. Chem. 51, 897, (1973).
7. D. A. Dawson and W. F. Reynolds, Can. J. Chem. 53, 373, (1975).
8. J. Fukunaga and R. W. Taft, J. Amer. Chem. Soc. 97, 1612, (1975).
9. W. J. Hehre, R. F. Stewart, and J. A. Pople, J. Chem. Phys. 51, 2657, (1969).
10. R. D. Topsom, Prog. Phys. Org. Chem.(this volume), p. 1.
11. A. R. Katritzky and R. D. Topsom, Angew. Chem. Int. Ed. Engl. 9, 87, (1970).
12. L. Libit and R. Hoffmann, J. Amer. Chem. Soc. 96, 1370, (1974).
13. D. G. Lister, J. K. Tyler, J. H. Høg, and N. W. Larsen, J. Mol. Struct. 23,253 (1974). The calculated STO-3G equilibrium structure for aniline indicates significant nonplanarity at nitrogen.
14. W. J. Hehre, L. Radom, and J. A. Pople, Chem. Commun. 1972, 669.
15. T. B. Grindley, A. R. Katritzky, and R. D. Topsom, J. Chem. Soc. Perkin II. 1974, 289.
16. G. P. Ford, A. R. Katritzky, and R. D. Topsom, J. Chem. Soc Perkin II. 1975, 1378.
17. See, for example; L. Radom, J. A. Pople, and P. v. R. Schleyer, J. Amer. Chem. Soc. 94, 5935, (1972).
18. J. F. Wolf, R. G. Harch, R. W. Taft, and W. J. Hehre, J. Amer. Chem. Soc. 97, 2902, (1975).
19. R. T. C. Brownlee, S. Ehrenson, and R. W. Taft, Prog. Phys. Org. Chem. 10, 1, (1973).
20. P. R. Wells, S. Ehrenson, and R. W. Taft, Prog. Phys. Org. Chem. 6, 147, (1968).
21. R. T. C. Brownlee and R. W. Taft, J. Amer. Chem. Soc. 90, 6537, (1968).
22. L. Radom, W. J. Hehre, J. A. Pople, G. L. Carlson, and W. G. Fateley, Chem. Commun. 1972, 308.
23. W. G. Fateley, Pure Appl. Chem. 36, 109, (1973).
24. Y. Yukawa, Y. Tsuno, and N. Shimizu, Bull. Chem. Soc., Jap. 44, 2843, (1971).
25. K. Hayamizu and O. Yamamoto, J. Mol. Spectrosc. 28,89 (1968); 29,183 (1969).
26. See, W. N. Lipscomb, Adv. Mag. Resonance. 2, 138, (1967).
27. R. Ditchfield and P. D. Ellis, in Topics in Carbon-13 NMR Spectroscopy.Vol. I, G. C. Levy, Ed., Wiley, New York, 1974.
28. A. Saika and C. P. Slichter, J. Chem. Phys. 22, 26, (1954).
29. The term "ring current" is only a convenient shorthand for a particular mathematical expression that appears in the theorysee: H. G. Ff. Roberts, Mol. Phys. 27, 843, (1974).
30. O. Kajimoto and T. Fueno, Chem. Lett. 1972, 103.
31. See, for example: T. Tokuhior, N. K. Wilson, and G. Fraenkel, J. Amer. Chem. Soc. 90, 3622, (1968).
32. J. F. Sebastian and J. R. Grunwell, Can. J. Chem. 49, 1779, (1971).
33. T. B. Cobb and J. D. Memory, J. Chem. Phys. 50, 4262, (1969).
34. H. P. Figeys and R. Flammang, Mol. Phys. 12, 581, (1967).
35. H. Sterk and H. Holzer, Org. Mag. Resonance. 6, 133, (1974).
36. See, for example: M. T. Tribble and J. G. Traynham, in Advances in Linear Free Energy Relationships.N. B. Chapman, and J. Shorter, Eds., Plenum, London, 1972.
37. B. M. Lynch, Org. Mag. Resonance. 6, 190, (1974).
38. D. A. Dawson, G. K. Hamer, and W. F. Reynolds, Can. J. Chem. 52, 39, (1974).
39. P. Lazzeretti and F. Taddei, Mol. Phys. 22, 941, (1971).
40. J. Niwa, Bull. Chem. Soc Jap. 48, 1637, (1975).
41. G. L. Nelson, G. C. Levy, and J. D. Cargioli, J. Amer. Chem. Soc. 94, 3089, (1972).
42. H. Spiesecke and W. G. Schneider, J. Chem. Phys. 35, 731, (1961).
43. T. K. Wu and B. P. Dailey, J. Chem. Phys. 41, 2796, (1964).
44. G. E. Maciel, in Topics in Carbon-13 NMR Spectroscopy.G. C. Levy, Ed., Wiley, New York, 1974. [See also J. W. Larsen and P. A. Bouis, J. Amer. Chem. Soc. 97,4418 (1975) for a similar argument in carbocations.].
45. G. L. Martin, M. L. Martin, and S. Odiot, Org. Mag. Resonance. 7, 2, (1975).
46. J. Mason, J. Chem. Soc. (A). 1971, 1038.
47. R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Amer. Chem. Soc.55,709(1963).
48. R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis, J. Amer. Chem. Soc. 85, 3146, (1963).
49. M. Karplus and T. P. Das, J. Chem. Phys. 34, 1683, (1961).
50. F. Prosser and L. Goodman, J. Chem. Phys. 38, 374, (1963).
51. M. J. S. Dewar and J. Kelemen, J. Chem. Phys. 49, 499, (1968).
52. G. E. Maciel and J. J. Natterstad, J. Chem. Phys. 42, 2427, (1965).
53. W. Adcock and M. J. S. Dewar, J. Amer. Chem. Soc. 89, 379, (1967).
54. R. T. C. Brownlee, S. K. Dayal, J. L. Lyle, and R. W. Taft, J. Amer. Chem. Soc. 94, 7208, (1972).
55. J. A. Bromilow, R. T. C. Brownless, R. D. Topsom and R. W. Taft, J. Amer. Chem. Soc.. 98, 2020, (1976).