2-pyridone and derivatives: Gas-phase acidity, proton affinity, tautomer preference, and leaving group ability

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1623-1631

  Michelson, Anna Zhachkina ^a   Petronico, Aaron ^a   Lee, Jeehiun K ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PYRIDONES; DELOCALIZATIONS; FUNDAMENTAL PROPERTIES; GAS-PHASE ACIDITIES; GASPHASE; LEAVING GROUPS; PROTON AFFINITY; PYRIDONES;

ACIDITY; MASS SPECTROMETRY;

PROTONS;

2 PYRIDONE DERIVATIVE; 3 CHLORO 2 PYRIDONE; 3 FORMYL 2 PYRIDONE; PROTON; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; BINDING AFFINITY; GAS; REACTION ANALYSIS; STRUCTURE ANALYSIS; TAUTOMER;

ACIDS; GASES; HYDROCHLORIC ACID; KINETICS; MASS SPECTROMETRY; MODELS, CHEMICAL; PROTONS; PYRIDONES; STEREOISOMERISM; THERMODYNAMICS; URACIL;

EID: 84863164978     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201991y     Document Type: Article

References (57)

1. Berti, P. J.; McCann, J. A. B. Chem. Rev. 2006, 106, 506-555
2. Stivers, J. T.; Drohat, A. C. Arch. Biochem. Biophys. 2001, 396, 1-9
3. Kurinovich, M. A.; Lee, J. K. J. Am. Chem. Soc. 2000, 122, 6258-6262
4. Kurinovich, M. A.; Lee, J. K. J. Am. Soc. Mass Spectrom. 2002, 13, 985-995
5. Zhachkina, A.; Lee, J. K. J. Am. Chem. Soc. 2009, 131, 18376-18385
6. Walsh, C. Enzymatic Reaction Mechanisms; Freeman: San Francisco, 1979.
7. Pullman, B.; Pullman, A. Adv. Heterocycl. Chem. 1971, 13, 77-159
8. Kwiatkowski, J. S.; Pullman, B. Adv. Heterocycl. Chem. 1975, 18, 199-335
9. Sonnenberg, J. L.; Wong, K. F.; Voth, G. A.; Schlegel, B. J. Chem. Theory Comput. 2009, 5, 949-961 and references therein
10. Beak, P. Acc. Chem. Res. 1977, 10, 186-192
11. Sato, H.; Hirata, F.; Sakaki, S. J. Phys. Chem. A 2004, 108, 2097-2102
12. Hatherley, L. D.; Brown, R. D.; Godfrey, P. D.; Pierlot, A. P.; Caminati, W.; Damiani, D.; Melandri, S.; Favero, L. B. J. Phys. Chem. 1993, 97, 46-51
13. Nowak, M. J.; Lapinski, L.; Fulara, J.; Les, A.; Adamowicz, L. J. Phys. Chem. 1992, 96, 1562-1569
14. De Kowalewski, D. G.; Contreras, R. H.; Diez, E.; Esteban, A. Mol. Phys. 2004, 102, 2607-2615
15. Furlong, J. J. P.; Mercedes Schiavoni, M.; Castro, E. A.; Allegretti, P. E. Russ. J. Org. Chem. 2008, 44, 1725-1736
16. Cook, M. J.; Katritzky, A. R. Tetrahedron Lett. 1976, 31, 2685-2688
17. Beak, P.; Fry, F. S. J. Am. Chem. Soc. 1973, 95, 1700-1702 and references therein
18. Piacenza, M.; Grimme, S. J. Comput. Chem. 2004, 25, 83-99
19. Fu, A.; Li, H.; Du, D.; Zhou, Z. J. Phys. Chem. A 2005, 109, 1468-1477
20. Maris, A.; Ottaviani, P.; Caminati, W. Chem. Phys. Lett. 2002, 360, 155-160
21. Hazra, M. K.; Chakraborty, T. J. Phys. Chem. A 2006, 110, 9130-9136
22. Barone, V.; Adamo, C. J. Phys. Chem. 1995, 99, 15062-15068
23. Dkhissi, A.; Houben, L.; Smets, J.; Adamowicz, L.; Maes, G. J. Mol. Struct. 1999, 484, 215-227
24. Tsuchida, N.; Yamabe, S. J. Phys. Chem. A 2005, 109, 1974-1980
25. Sharma, S.; Lee, J. K. J. Org. Chem. 2004, 69, 7018-7025
26. Sharma, S.; Lee, J. K. J. Org. Chem. 2002, 67, 8360-8365
27. Sun, X.; Lee, J. K. J. Org. Chem. 2007, 72, 6548-6555
28. Liu, M.; Xu, M.; Lee, J. K. J. Org. Chem. 2008, 73, 5907-5914
29. Liu, M.; Li, T.; Amegayibor, S.; Cardoso, D. S.; Fu, Y.; Lee, J. K. J. Org. Chem. 2008, 73, 9283-9291
30. Kurinovich, M. A.; Lee, J. K. Chem. Commun. 2002, 2354-2355
31. Zhachkina, A.; Liu, M.; Sun, X.; Amegayibor, S.; Lee, J. K. J. Org. Chem. 2009, 74, 7429-7440
32. Lee, J. K. Int. J. Mass Spectrom. 2005, 240, 261-272
33. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
34. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
35. Wheeler, S. E.; Moran, A.; Pieniazek, S. N.; Houk, K. N. J. Phys. Chem. A 2009, 113, 10376-10384
36. Guimon, C.; Garrabe, G.; Pfister-Guillouzo, G. Tetrahedron Lett. 1979, 28, 2585-2588
37. Brown, R. S.; Tse, A.; Vederas, J. C. J. Am. Chem. Soc. 1980, 102, 1174-1176
38. NIST Chemistry WebBook, NIST Standard Reference Database Number 69; retrieved in 2011. Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, http://webbook.nist.gov.
39. Eyet, N.; Villano, S. M.; Bierbaum, V. M. Int. J. Mass Spectrom. 2009, 283, 26-29
40. Although generally electrospray is believed to be a soft ionization technique that vaporizes solution-phase ions with integrity, there do exist examples whereby some structures when electrosprayed can isomerize in the desolvation process, though this has not been shown for pyridones: Tian, Z.; Kass, S. R. J. Am. Chem. Soc. 2008, 130, 10842-10843 and references therein
41. Gronert, S.; Feng, W. Y.; Chew, F.; Wu, W. Int. J. Mass Spectrom. 2000, 195/196, 251-258
42. Ritchie, C. D.; Sager, W. F. Prog. Phys. Org. Chem. 1964, 2, 323-400
43. Hansch, C.; Leo, A.; Unger, S.; Kim, K. H.; Nikaitani, D. J. Med. Chem. 1973, 16, 1207-1216
44. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley-Interscience: New York, 1979.
45. Chesnavich, W. J.; Su, T.; Bowers, M. T. J. Chem. Phys. 1980, 72, 2641-2655
46. Su, T.; Chesnavich, W. J. J. Chem. Phys. 1982, 76, 5183-5185
47. Cooks, R. G.; Kruger, T. L. J. Am. Chem. Soc. 1977, 99, 1279-1281
48. McLuckey, S. A.; Cameron, D.; Cooks, R. G. J. Am. Chem. Soc. 1981, 103, 1313-1317
49. McLuckey, S. A.; Cooks, R. G.; Fulford, J. E. Int. J. Mass Spectrom. and Ion Physics 1983, 52, 165-174
50. Brodbelt-Lustig, J. S.; Cooks, R. G. Talanta 1989, 36, 255-260
51. Green-Church, K. B.; Limbach, P. A. J. Am. Soc. Mass Spectrom. 2000, 11, 24-32
52. Fenn, J. B.; Mann, M.; Meng, C. K.; F., W. S.; Whitehouse, C. M. Science 1989, 246, 64-71
53. Drahos, L.; Vékey, K. J. Mass Spectrom. 1999, 34, 79-84
54. Kohn, W.; Becke, A. D.; Parr, R. G. J. Chem. Phys. 1996, 100, 12974-12980
55. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
56. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
57. Frisch, M. J. Gaussian 09; Gaussian, Inc.: Wallingford CT, 2009.