Intramolecular hydrogen bonding in 2-hydroxybenzoyl compounds: Infrared spectra and quantum chemical calculations

Journal of Physical Chemistry

Volumn 100, Issue 18, 1996, Pages 7418-7425

  Lampert, Heike ^a   Mikenda, Werner ^a   Karpfen, Alfred ^b  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001401948     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp953527k     Document Type: Article

References (44)

1. Steinwender, E.; Mikenda, W. Monatsh. Chem. 1994, 125, 695. The experimentally determined sequence of hydrogen bond strengths was acid chloride < tertiary amides < acids ≈ esters < aldehyde < ketone < secondary and primary amides < salts.
2. (a) Schaefer, T.; Sebastian, R.; Laatikainen, R.; Salman, S. R. Can. J. Chem. 1984, 62, 326.
3. (b) Onda, M.; Asai, M.; Kohno, T.; Kikuchi, J.; Yamaguchi, I. J. Mol. Struct. 1987, 162, 183.
4. (c) Nagaoka, S.; Nagashima, U. Chem. Phys. 1989, 136, 153.
5. (d) Nagashima, U.; Nagaoka, S.; Katsumata, S. J. Phys. Chem. 1991, 95, 3532.
6. Estevez, C. M.; Rios, M. A.; Rodriguez, J. Struct. Chem. 1992, 3, 381.
7. Coussens, B.; Pierlot, K.; Meier, R. J. THEOCHEM 1992, 259, 331.
8. Nagy, P. I.; Dunn, W. J.; Alagona, G.; Ohio, C. J. Phys. Chem. 1993, 97, 4628.
9. Nagy, P. I.; Smith, D. A.; Alagona, G.; Ghio, C. J. Phys. Chem. 1994, 98, 486.
10. George, P.; Bock, C. W.; Trachtman, M. THEOCHEM 1985, 133, 11.
11. Penner, G. H.; George, P.; Bock, C. W. THEOCHEM 1987, 152, 201.
12. Silvestro, T.; Topsom, R. D. J. Mol. Struct. 1990, 206, 309.
13. Grana, A. M.; Rios, M. A.; Rodriguez, J. Struct. Chem. 1991, 2, 575.
14. Schaefer, T.; Sebastian, R.; McKinnon, D. M.; Spevak, P. W.; Cox, K. J.; Takeuchi, C. S. Can. J. Chem. 1993, 71, 960.
15. Cough, K. M.; Wildman, T. A. J. Am. Chem. Soc. 1990, 112, 9141.
16. Vener, M. V.; Scheiner, S. J. Phys. Chem. 1995, 99, 642.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzales, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision G.4; Gaussian, Inc.: Pittsburgh, PA, 1993.
18. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939.
19. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
20. Lower level calculations (including semiempirical ones) did not provide reasonable results; results at the HF/6-31G level were slightly worse than those considered in the paper.
21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
22. Lee, C.; Yang, W.; Parr, P. G. Phys. Rev. B 1988, 37, 785.
23. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
24. Michels, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
25. Due to the partially extremely low solubilities and partial pressures of the 4-hydroxybenzoyl compounds, solution and gas-phase IR spectra could be obtained in only a few instances; they are not included in Table 2.
26. (a) Mikenda, W.; Steinwender, E.; Mereiter, K. Monatsh. Chem. 1995, 126, 495.
27. (b) Mikenda, W.; Pertlik, F.; Steinwender, E. Monatsh. Chem. 1993, 124, 867.
28. (c) Pertlik, F. Z. Kristallogr. 1992, 202, 17.
29. (d) Pertlik, F. Monatsh. Chem. 1990, 121, 129.
30. (e) Pertlik, F. Monatsh. Chem. 1987, 118, 1349.
31. (f) Bacon, G. E.; Jude, R. E. Z. Kristallogr. 1973, 138, 19.
32. (a) Kallel, A.; Amor, B. H.; Svoboda, I.; Fuess, H. Z. Kristallogr. 1992, 198, 137.
33. (b) Qi Gao; Jeffrey, G. A.; Ruble, J. R.; McMullen, R. K. Acta Crystallogr., Sect. B 1991, 47, 742.
34. (c) Feld, R.; Lehmann, M. S.; Muir, K. W.; Speakman, J. C. Z. Kristallogr. 1981, 157, 215.
35. (d) Leiserowitz, L.; Tuval, M. Acta Crystallogr., Sect. B 1978, 34, 1230.
36. (e) Lobanova, G. M. Kristallografiya 1968, 13, 984.
37. (a) Heath, E. A.; Singh, P.; Ebisuzaki, Y. Acta Crystalhgr., Sect. C 1992, 48, 1960.
38. (b) Kashino, S.; Tateno, S.; Tanabe, H.; Haisa, M.; Katsube, Y. Acta Crystallogr., Sect. C 1991, 47, 2236.
39. (c) Xianti, L.; Huaxue, J. J. Struct. Chem. 1983, 2, 213.
40. (d) Iwasaki, F. Acta Crystallogr., Sect. B 1977, 33, 1646.
41. More details of vibrational spectroscopic data will be presented elsewhere.
42. Whalley, E. In The Hydrogen Bond; Schuster, P., Zundel, G., Sandorfy, C., Eds., North Holland: Amsterdam, The Netherlands, 1976; Vol. III, Chapter 29, p 1425.
43. Mikenda, W.; Mereiter, K.; Preisinger, A. Inorg. Chim. Acta 1989, 161, 21.
44. Slupecki, O.; Brown, I. D. Acta Crystallogr., Sect. B 1982, 38, 1078.