Steric inhibition of resonance: A revision and quantitative estimation on the basis of aromatic carboxylic acids

Chemistry - A European Journal

Volumn 6, Issue 18, 2000, Pages 3391-3398

  Böhm, Stanislav ^a   Exner, Otto ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acidity; Carboxylic acids; Hindered resonance; Ortho effect; Steric hindrance

Indexed keywords

2,3,5,6 TETRAMETHYLBENZOIC ACID; AROMATIC CARBOXYLIC ACID; BENZOIC ACID DERIVATIVE; ORTHO TOLUIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; ELECTROCHEMISTRY; MOLECULAR DYNAMICS; QUANTUM CHEMISTRY; STEREOSPECIFICITY;

EID: 0038997510     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000915)6:18<3391::AID-CHEM3391>3.0.CO;2-X     Document Type: Article

References (54)

1. R. H. Birtles, G. C. Hampson, J. Chem. Soc. 1937, 10 ; However, resonance and its inhibition in nitrobenzene are very weak: O. Exner, T. M. Krygowski, Chem. Soc. Rev. 1996, 25, 71 ; S. Irle, T. M. Krygowski, J. E. Niu, W. H. E. Schwarz, J. Org. Chem. 1995, 60, 6744.
2. R. H. Birtles, G. C. Hampson, J. Chem. Soc. 1937, 10 ; However, resonance and its inhibition in nitrobenzene are very weak: O. Exner, T. M. Krygowski, Chem. Soc. Rev. 1996, 25, 71 ; S. Irle, T. M. Krygowski, J. E. Niu, W. H. E. Schwarz, J. Org. Chem. 1995, 60, 6744.
3. R. H. Birtles, G. C. Hampson, J. Chem. Soc. 1937, 10 ; However, resonance and its inhibition in nitrobenzene are very weak: O. Exner, T. M. Krygowski, Chem. Soc. Rev. 1996, 25, 71 ; S. Irle, T. M. Krygowski, J. E. Niu, W. H. E. Schwarz, J. Org. Chem. 1995, 60, 6744.
4. a) C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, New York, 1953, Chapter 46e;
5. b) H. C. Brown, D. H. McDaniel, O. Häfliger in Determination of Organic Structures by Physical Methods (Eds.: E. A. Braude, F. C. Nachod), Academic Press, New York, 1955, p. 567;
6. c) M. Charton in Similarity Models in Organic Chemistry, Biochemistry and Related Fields (Eds.: R. L. Zalewski, T. M. Krygowski, J. Shorter), Elsevier, Amsterdam, 1991, p. 629.
7. a) S. H. Pine, J. B. Hendrickson, D. J. Cram, G. S. Hammond, Organic Chemistry, 4th ed., McGraw Hill, New York, 1980, p. 224;
8. b) J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, pp. 36-38;
9. c) T. W. G. Solomons, Organic Chemistry, 5th ed., Wiley, New York, 1992, pp. 486-489.
10. E. A. Braude, F. Sondheimer, W. F. Forbes, Nature 1954, 173, 117.
11. a) J. Burgers, M. A. Hoefnagel, P. E. Verkade, H. Wisser, B. M. Wepster, Recl. Trav. Chim. Pays-Bas 1958, 77, 491;
12. b) H. Ahlbrecht, E. O. Duber, J. Epsztajn, R. M. K. Marcinkowski, Tetrahedron 1984, 40, 1157;
13. c) S. Böhm, M. Decouzon, O. Exner, J.-F. Gal, P.-C. Maria, J. Org. Chem. 1994, 59, 8127.
14. a) J. F. J. Dippy, S. R. C. Hughes, J. W. Laxton, J. Chem. Soc. 1954, 1470;
15. b) J. Guilleme, E. Diez, F. J. Bermejo, Magn. Reson. Chem. 1985, 23, 449;
16. c) A. L. Baumstark, P. Balakrishnan, M. Dotrong, C. J. McCloskey, M. G. Oakley, D. W. Boykin, J. Am. Chem. Soc. 1987, 109, 1059;
17. d) J. M. Wilson, N. E. Gore, J. E. Sawbridge, F. Cardenas-Cruz, J. Chem. Soc. B 1967, 852;
18. e) M. Charton, Prog. Phys. Org. Chem. 1971, 8, 235.
19. I. V. Tselinskii, P. B. Levit, V. A. Shlyapochnikov, Zh. Obshch. Khim. 1992, 62, 173.
20. F. H. Westheimer in Steric Effects in Organic Chemistry (Ed.: M. S. Newman), Wiley, New York, 1956, p. 523.
21. V. Všetečka, O. Exner, Collect. Czech. Chem. Commun. 1974, 39, 1140.
22. B. Tinant, J.-P. Declercq, M. van Meerssche, O. Exner, Collect. Czech. Chem. Commun. 1988, 53, 301.
23. a) M. Decouzon, P. Ertl, O. Exner, J.-F. Gal, P.-C. Maria, J. Am. Chem. Soc. 1993, 775, 12071;
24. b) M. Decouzon, J.-F. Gal, P.-C. Maria, S. Böhm, P. Jiménez, M. V. Roux, O. Exner, New J. Chem. 1997, 21, 561;
25. c) P. Fiedler, O. Exner, J. Phys. Org. Chem. 1998, 11, 141.
26. a) P. George, M. Trachtman, C. W. Bock, A. M. Brett, J. Chem. Soc. Perkin Trans 2 1976, 1222;
27. b) O. Exner, Prog. Phys. Org. Chem. 1990, 18, 129.
28. -1 was obtained for all twenty methyl-substituted benzoic acids, see ref. [11b].
29. A combination of calculated and experimental values was used by us previously in the case of the less reliable AMI calculations, see ref. [5c].
30. R. Anca, S. Martinez-Carrera, S. Garcia-Blanco, Acta Crystallogr. 1967, 23, 110.
31. Recently an equilibrium of two planar forms was proven for methyl 2-methylbenzoate in the gas phase by electron diffraction: D. Hnyk, K. B. Borisenko, S. Samdal, O. Exner, Eur. J. Org. Chem. 2000, 2063.
32. a) O. Pytela, J. Liška, Collect. Czech. Chem. Commun. 1994, 59, 2005;
33. b) J. Kulhánek, O. Exner, J. Chem. Soc. Perkin Trans. 2 1998, 1397.
34. a) F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans 2 1987, S1;
35. b) F. H. Allen, S. Bellard, M. D. Brice, B. A. Cartwright, A. Doubleday, H. Higgs, T. Hummelink, B. G. Hummelink-Peters, O. Kennard, W. D. S. Motherwell, R. J. Rodgers, D. G. Watson, Acta Crystallogr. Sect B 1979, 35, 2331.
36. O. Exner, Paper Presented at the 8th Meeting on Stereochemistry, Teplá near Marienbad (Czech Republic), 1998; O. Exner, Chem. Listy 1998, 92, 235.
37. O. Exner, Paper Presented at the 8th Meeting on Stereochemistry, Teplá near Marienbad (Czech Republic), 1998; O. Exner, Chem. Listy 1998, 92, 235.
38. N. L. Allinger, K. Chen, M. Rahman, A. Pathiaseril, J. Am. Chem. Soc. 1991, 773, 4505.
39. Cambridge Structural Database, see ref. [18b], 1997 Version.
40. J. W. Long, J. L. Franklin, J. Am. Chem. Soc. 1974, 96, 2320.
41. T. B. McMahon, P. Kebarle, J. Am. Chem. Soc. 1977, 99, 2222.
42. R. W. Taft, R. D. Topsom, Prog. Phys. Org. Chem. 1987, 76, 1.
43. A. I. Vogel, J. Chem. Soc. 1948, 1846.
44. 3) was also calculated and subtracted.
45. O. Exner, Z. Friedl, Prog. Phys. Org. Chem. 1993, 79, 259.
46. Our new definition of BE, see ref. [29], is more general and more exact than the original one, see ref. [8], but leads to the same results in the classical examples. However, the term "Buttressing Effect" is somewhat out-of-date and does not agree with real examples, particularly for more remote groups. In all cases, the acronym BE can be read as "Boost Energy". We thank Dr. J. Shorter for suggesting this term, which is applicable and physically correct in all examples.
47. M. Decouzon, O. Exner, J.-F. Gal, P.-C. Maria, J. Chem. Soc. Perkin Trans. 2 1996, 475.
48. I. Císařová, J. Podlaha, S. Böhm, O. Exner, Collect. Czech. Chem. Commun. 2000, 65, 216.
49. S. T. Howard, T. M. Krygowski, A. Cieselski, M. Wisiorowski, Tetrahedron 1998, 54, 3533; T. M. Krygowski, E. Piȩtka, R. Anulewicz, M. K. Cyrański, J. Nowacki, Tetrahedron 1998, 54, 12289.
50. S. T. Howard, T. M. Krygowski, A. Cieselski, M. Wisiorowski, Tetrahedron 1998, 54, 3533; T. M. Krygowski, E. Piȩtka, R. Anulewicz, M. K. Cyrański, J. Nowacki, Tetrahedron 1998, 54, 12289.
51. O. Exner, S. Böhm, J. Chem. Soc. Perkin Trans. 2 1997, 1235.
52. O. Exner, Org. React. Tartu 1995, 29, 1.
53. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzales, J. A. Pople, Gaussian 94, Revision C.3, Gaussian, Pittsburgh, 1995.
54. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.