Overlooked Difference between Hydrogen Bonds of Equal Strength Formed between Catechol and an Oxygen or Nitrogen Base. Experiments and DFT Calculations

Journal of the American Chemical Society

Volumn 125, Issue 47, 2003, Pages 14642-14647

  Foti, Mario C ^a   DiLabio, Gino A ^b   Ingold, K U ^b  

^a CNR   (Italy)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DISCRETE FOURIER TRANSFORMS; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; PROTONS;

FUNCTIONAL GROUPS; INTRAMOLECULAR REACTION;

HYDROGEN BONDS;

CARBON TETRACHLORIDE; CATECHOL; HYDROGEN; NITROGEN; OXYGEN; PROTON;

ARTICLE; CALCULATION; CHEMICAL BOND; DENSITY FUNCTIONAL THEORY; EXPERIMENT; HYDROGEN BOND; HYPOTHESIS; INFRARED RADIATION;

EID: 0344443304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036168c     Document Type: Article

References (27)

1. Foti, M. C.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 12 881-12 888.
2. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans 2 1990, 521-529.
3. (a) Astolfi, P.; Greci, L.; Paul, T.; Ingold, K. U. J. Chem. Soc., Perkin Trans 2 2001, 1631-1633.
4. (b) Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
5. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans 2 1989, 699-711.
6. H value well defined and, by implication, independent of the base.
7. (a) Pratt, D. A.; Wright, J. S.; Ingold, K. U. J. Am. Chem. Soc. 1999, 121, 4877-4882.
8. (b) Pratt, D. A.; de Heer, M. I.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 5518-5526.
9. (c) Pratt, D. A.; DiLabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 11 085-11 092.
10. (d) DiLabio, G. A.; Litwinienko, G.; Lin, S.; Pratt, D. A.; Ingold, K. U. J. Phys. Chem. A 2002, 106, 11 719-11 725.
11. A detailed description of the changes in the IR spectrum of 3,5-di-tertbutylcatechol as a function of DMSO concentration has been given previously.
12. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
13. (b) Lee, C.; Yang, W.: Parr, R. G. Phys Rev. B. 1988, 37, 785-789.
14. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16 502-16 513.
15. Korth, H.-G.; de Heer, M. I.; Mulder, P. J. Phys. Chem. A 2002, 106, 8779-8789.
16. See, for example: Schwenke, D. W.; Truhlar, D. G. J. Chem. Phys. 1985, 82, 2418-2426, and references therein.
17. Gurka, D.; Taft, R. W. J. Am. Chem. Soc. 1969, 91, 4794-4801.
18. This experimental value is for 2-butanone.
19. Version 3.1 is implemented in the Gaussian-98 program package15 and used in the present work. A more recent version of the program is NBO 4.M Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F., Theoretical Chemistry Institute, University of Wisconsin, Madison 1999.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C. ; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 11.3, Gaussian, Inc., Pittsburgh, PA, 2002. This package was used for all the calculations in the present work.
21. 10
22. Del Bene, J. E.: Person, W. R.; Szczepaniak, K. J. Phys. Chem. 1995, 99, 10 705-10 707.
23. 19 δσ values (Table 4) could make this distinction.
24. 20 at the B3LYP/6-31 I G(d)//B3LYP/6-31G(d) level.
25. (a) Ditchfield, R. Mol. Phys. 1974, 27, 789-807,
26. (b) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 8251-8260.
27. intra for any of the catechol - - - HBA complexes, see Table 2. footnote c.