The interaction of carbonyl groups with substituents

Accounts of Chemical Research

Volumn 32, Issue 11, 1999, Pages 922-929

  Wiberg, Kenneth B ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE;

CHEMICAL BOND; DISSOCIATION; ENERGY TRANSFER; HYDRATION; MOLECULAR INTERACTION; POLARIZATION; PROTEIN PROTEIN INTERACTION; RESEARCH; REVIEW;

EID: 0032728625     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar990008h     Document Type: Review

References (42)

1. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. Gaussian-2 Theory for Molecular Energies of First- and Second-Row Elements. J. Chem. Phys. 1991, 94, 7221.
2. Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. A Complete Basis Set Model Chemistry 5. Extensions to Six or More Heavy Atoms. J. Chem. Phys. 1996, 104, 2598.
3. Ochterski, J.; Petersson, G A.; Wiberg, K. B. A Comparison of Model Chemistries. J. Am. Chem. Soc 1993, 115, 9234.
4. Wiberg, K. B.; Rablen, P. R. Substituent Effects. 5. Vinyl and Ethynyl Derivatives. J. Am. Chem. Soc. 1993, 115, 9234. Cf.: Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. Substituent Effects. 4. Nature of Substituent Effects at Carbonyl Groups. J. Am. Chem. Soc. 1992, 114, 8644.
5. Wiberg, K. B.; Rablen, P. R. Substituent Effects. 5. Vinyl and Ethynyl Derivatives. J. Am. Chem. Soc. 1993, 115, 9234. Cf.: Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. Substituent Effects. 4. Nature of Substituent Effects at Carbonyl Groups. J. Am. Chem. Soc. 1992, 114, 8644.
6. Wiberg, K. B.; Rablen, P. R.; Rush, D.; Keith, T. A. Amides. 3. Experimental and Theoretical Studies of the Effect of the Medium on the Rotational Barriers for N, N.-Dimethylformamide and N, N.-Dimethylacetamide. J. Am. Chem. Soc. 1995, 117, 4261.
7. Taha, A. N.; Crawford, S. M. N.; True, N. S. Determination of the Internal Rotational Barrier of Formamide from Gas-Phase NMR Spectra, J. Am. Chem. Soc. 1998, 120, 1934.
8. Blom, C. E.; Gunthard, Hs. H. Rotational Isomerism in Methyl Formate and Methyl Acetate. Chem. Phys. Lett. 1981, 84, 267.
9. Neugebauer, C. S. M.; Taha, A. N.; True, N. S.; LeMaster, C. B. Gas-Phase NMR Studies of N,N-Dimethylthioamides. J. Phys. Chem. 1997, 101, 4699.
10. Sandström, J. Barriers to Internal Rotation in Thioamides. J. Phys. Chem. 1967, 71, 2318. Neuman, R. C., Jr.; Young, L. B. Hindered Rotation and Carbon- 13-Hydrogen Coupling Constants in Amides, Thioamides and Amidines. J. Phys. Chem. 1965, 69, 2570. Stewart, W. E.; Siddall, T. H., III. Nuclear Magnetic Resonance Studies of Amides. Chem. Rev. 1970, 70, 517.
11. Sandström, J. Barriers to Internal Rotation in Thioamides. J. Phys. Chem. 1967, 71, 2318. Neuman, R. C., Jr.; Young, L. B. Hindered Rotation and Carbon-13-Hydrogen Coupling Constants in Amides, Thioamides and Amidines. J. Phys. Chem. 1965, 69, 2570. Stewart, W. E.; Siddall, T. H., III. Nuclear Magnetic Resonance Studies of Amides. Chem. Rev. 1970, 70, 517.
12. Sandström, J. Barriers to Internal Rotation in Thioamides. J. Phys. Chem. 1967, 71, 2318. Neuman, R. C., Jr.; Young, L. B. Hindered Rotation and Carbon- 13-Hydrogen Coupling Constants in Amides, Thioamides and Amidines. J. Phys. Chem. 1965, 69, 2570. Stewart, W. E.; Siddall, T. H., III. Nuclear Magnetic Resonance Studies of Amides. Chem. Rev. 1970, 70, 517.
13. Wiberg, K. B.; Rablen, P. R., Why Does Thioformamide Have a Larger Rotational Barrier than Formamide? J. Am. Chem. Soc. 1995, 117, 2201.
14. The data are taken from Landolt-Bornstein, New Series; Springer-Verlag: Berlin, 1961, II/7; 1992, II/ 21; 1995, II/23.
15. The data are taken from Landolt-Bornstein, New Series; Springer-Verlag: Berlin, 1961, II/7; 1992, II/ 21; 1995, II/23.
16. The data are taken from Landolt-Bornstein, New Series; Springer-Verlag: Berlin, 1961, II/7; 1992, II/ 21; 1995, II/23.
17. See ref 3 for a summary of experimental bond dissociation energies.
18. Coulson, C. A. Valence; Oxford University Press: Oxford, UK, 1952; p 200.
19. For some recent studies, see: Glendenning, E. D.; Hrabal, J. A., II. Resonance in Formamide and its Chalchone Replacement Analogs. J. Am. Chem. Soc. 1997, 119, 9478. Lauvergnat, D.; Hiberty, P. C. Role of Conjugation in the Stabilities and Rotational Barriers of Formamides and Thioformamides. J. Am. Chem. Soc. 1997, 119, 9478.
20. For some recent studies, see: Glendenning, E. D.; Hrabal, J. A., II. Resonance in Formamide and its Chalchone Replacement Analogs. J. Am. Chem. Soc. 1997, 119, 9478. Lauvergnat, D.; Hiberty, P. C. Role of Conjugation in the Stabilities and Rotational Barriers of Formamides and Thioformamides. J. Am. Chem. Soc. 1997, 119, 9478.
21. Drakenberg, T.; Dahlquist, K. S.; Forsen, S. The Barrier to Internal Rotation in Amides. J. Phys. Chem. 1972, 76, 2178.
22. Greenberg, A.; Venzanzi, C. A. Structures and Energies of Two Bridgehead Lactones and their N- and O-Protonated Forms. J. Am. Chem. Soc. 1993, 115, 6951. Greenberg, A.; Moore, D. T.; Dubois, T. D. Small and Medium Sized Bridgehead Lactams. J. Am. Chem. Soc. 1996, 118, 8658.
23. Greenberg, A.; Venzanzi, C. A. Structures and Energies of Two Bridgehead Lactones and their N- and O-Protonated Forms. J. Am. Chem. Soc. 1993, 115, 6951. Greenberg, A.; Moore, D. T.; Dubois, T. D. Small and Medium Sized Bridgehead Lactams. J. Am. Chem. Soc. 1996, 118, 8658.
24. Fukui, K.; Fujimoto, H. A Molecular Orbital Theoretical Interpretation of Chemical Reactions. I. Bull. Chem. Soc. Jpn. 1968, 41, 1989. Fukui, K.; Fujimoto, H. MO-Theoretical Interpretation of the Nature of Chemical Reactions. II. Governing Principles. Bull. Chem. Soc. Jpn. 1969, 42, 3399.
25. Fukui, K.; Fujimoto, H. A Molecular Orbital Theoretical Interpretation of Chemical Reactions. I. Bull. Chem. Soc. Jpn. 1968, 41, 1989. Fukui, K.; Fujimoto, H. MO-Theoretical Interpretation of the Nature of Chemical Reactions. II. Governing Principles. Bull. Chem. Soc. Jpn. 1969, 42, 3399.
26. Wiberg, K. B.; Ochterski, J.; Streitwieser, A. Origin of the Acidity of Enols and Carboxylic Acids. J. Am. Chem. Soc. 1996, 118, 8291.
27. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas-Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.
28. Wiberg, K. B.; Laidig, K. E. Barriers to Rotation Adjacent to Double Bonds. 3. The C-O Barrier in Formic Acid, Methyl Formate, Acetic Acid, and Methyl Acetate. J. Am. Chem. Soc. 1987, 109, 5935.
29. Pauling, L. The Nature of the Chemical Bond, 2nd ed.; Cornell University Press: Ithaca, NY, 1944; p 203.
30. Reed, A. E.; Weinstock, R. B.; Weinhold, F., Natural Population Analysis. J. Chem. Phys. 1985, 93, 735. Reed, A.; Weinhold, F.; Curtiss, L. A. Intermolecular Interactions from a Natural Bond Orbital, Donor- Acceptor Viewpoint. Chem. Rev. 1988, 88, 899.
31. Reed, A. E.; Weinstock, R. B.; Weinhold, F., Natural Population Analysis. J. Chem. Phys. 1985, 93, 735. Reed, A.; Weinhold, F.; Curtiss, L. A. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint. Chem. Rev. 1988, 88, 899.
32. Bader, R. F. W. Atoms in Molecules. A Quantum Theory, Clarendon Press: Oxford, UK, 1990.
33. Hiberty, P. C.; Byrman, C. P. Role of π-Electron Delocalization in the Enhanced Acidity of Carboxylic Acids. J. Am. Chem. Soc. 1995, 117, 9875. Cf.: Bader, R. F. W.; Streitwieser, A.; Neuhaus, A.; Laidig, K. E.; Speers, P. Electron Delocalization and the Fermi Hole. J. Am. Chem. Soc. 1996, 118, 4959.
34. Hiberty, P. C.; Byrman, C. P. Role of π-Electron Delocalization in the Enhanced Acidity of Carboxylic Acids. J. Am. Chem. Soc. 1995, 117, 9875. Cf.: Bader, R. F. W.; Streitwieser, A.; Neuhaus, A.; Laidig, K. E.; Speers, P. Electron Delocalization and the Fermi Hole. J. Am. Chem. Soc. 1996, 118, 4959.
35. Wiberg, K. B.; Rosenberg, R. E. Charge Density Distribution in Acrolein, Butadiene and Vinylamine. Tetrahedron Lett. 1989, 30, 5981.
36. Bell, R. P. The Reversible Hydration of Carbonyl Compounds. Adv. Phys. Org. Chem. 1966, 4, 1.
37. Lipp, P.; Buchkremer, J.; Seeles, H. Studien in der Cyclopropan-Reihe. Cyclo-propanon. Ann. Chem. 1932, 499, 1
38. Wiberg, K. B.; Morgan, K. M.; Maltz, H. Thermochemistry of Carbonyl Reactions. 6. A Study of Hydration Equilibria. J. Am. Chem. Soc. 1994, 116, 11067.
39. Wiberg, K. B.; Crocker, L. S.; Morgan, K. M. Thermochemical Studies of Carbonyl Compounds. 5. Enthalpies of Reduction of Carbonyl Groups. J. Am. Chem. Soc. 1991, 113, 3447.
40. Kagen, H. B.; Riant, O. Catalytic Asymmetric Diels-Alder Reactions. Chem. Rev. 1992, 92, 1007. Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1, p 29.
41. Kagen, H. B.; Riant, O. Catalytic Asymmetric Diels- Alder Reactions. Chem. Rev. 1992, 92, 1007. Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1, p 29.
42. Reetz, M. T.; Hullmann, M.; Massa, W.; Berger, S.; Rademacher, P.; Heymanns, P. Structure and Electronic Nature of the Benzaldehyde-Boron Trifluoride Adduct. J. Am. Chem. Soc. 1986, 108, 2405.