What are the pKa values of C-H bonds in aromatic heterocyclic compounds in DMSO?

Tetrahedron

Volumn 63, Issue 7, 2007, Pages 1568-1576

  Shen, Kuang ^a   Fu, Yao ^a   Li, Jia Ning ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIMETHYL SULFOXIDE; HETEROCYCLIC COMPOUND; HYDROGEN;

ACCURACY; ACIDITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; PKA; PREDICTION; PRIORITY JOURNAL;

EID: 33846064670     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.032     Document Type: Article

References (77)

1. Joule J.A., and Mills K. Heterocyclic Chemistry (2000), Blackwell Science, Oxford
2. Katritzky A.R., and Pozharskii A.F. Handbook of Heterocyclic Chemistry (2003), Pergamon, Oxford
3. Xu Y., and Guo Q.-X. Heterocycles 63 (2004) 903-974
4. Chinchilla R., Najera C., and Yus M. Chem. Rev. 104 (2004) 2667-2722
5. Mallan J.M., and Bebb R.L. Chem. Rev. 69 (1969) 693-755
6. Marsais F., and Queguiner G. Tetrahedron 39 (1983) 2009-2011
7. Snieckus V. Chem. Rev. 90 (1990) 879-933
8. Ramon D.J., and Yus M. Eur. J. Org. Chem. 65 (2000) 225-237
9. Xu B., and Ma S.-M. Chin. J. Org. Chem. 20 (2000) 54-63
10. Mongin F., and Queguiner G. Tetrahedron 57 (2001) 4059-4090
11. Turck A., Ple N., Mongin F., and Queguiner G. Tetrahedron 57 (2001) 4489-4505
12. Gas-phase acidities of aromatic heterocycles:
13. DePuy C.H., Kass S.R., and Bean G.P. J. Org. Chem. 53 (1988) 4427-4433
14. Meot-Ner M., Liebman J.F., and Kafafi S.A. J. Am. Chem. Soc. 110 (1988) 5937-5941
15. Meot-Ner M., and Kafafi S.A. J. Am. Chem. Soc. 110 (1988) 6297-6303
16. Davico G.E., Bierbaum V.M., Depuy C.H., Ellison G.B., and Squires R.R. J. Am. Chem. Soc. 117 (1995) 2590-2599
17. Reed D.R., and Kass S.R. J. Mass Spectrom. 35 (2000) 534-539
18. a of aromatic heterocycles:
19. Fraser R.R., Mansour T.S., and Savard S. Can. J. Chem. 63 (1985) 3505-3509
20. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463 and references therein.
21. Other theoretical studies:
22. Smith B.J., and Radom L. J. Phys. Chem. 95 (1991) 10549-10551
23. Smith B.J., and Radom L. J. Am. Chem. Soc. 115 (1993) 4885-4888
24. Smith B.J., and Radom L. Chem. Phys. Lett. 231 (1994) 345-351
25. Ochterski J., Petersson G.A., and Wiberg K.B. J. Am. Chem. Soc. 117 (1995) 11299-11308
26. Bagno A., and Scorrano G. J. Phys. Chem. 100 (1996) 1536-1544
27. Martin J.M.L., and Lee T.J. Chem. Phys. Lett. 258 (1996) 136-143
28. Curtiss L.A., Raghavachari K., Redfern P.C., Rassolov V., and Pople J.A. J. Chem. Phys. 109 (1998) 7764-7776
29. Peterson K.A., Xantheas S.S., Dixon D.A., and Dunning Jr. T.H. J. Phys. Chem. A 102 (1998) 2449-2454
30. Hammerum S. Chem. Phys. Lett. 300 (1999) 529-532
31. Burk P., Koppel I.A., Koppel I., Leito I., and Travnikova O. Chem. Phys. Lett. 323 (2000) 482-489
32. Seo Y., Kim Y., and Kim Y. Chem. Phys. Lett. 340 (2001) 186-193
33. Pokon E.K., Liptak M.D., Feldgus S., and Shields G.C. J. Phys. Chem. A 105 (2001) 10483-10487
34. Ervin K.M., and DeTuri V.F. J. Phys. Chem. A 106 (2002) 9947-9956
35. Wiberg K.B. J. Org. Chem. 67 (2002) 4787-4794
36. Remko M. J. Phys. Chem. A 106 (2002) 5005-5010
37. Yi H.-B., Duan X.-H., Lee J.-Y., Li X.-Y., and Kim K.-S. J. Chem. Phys. 119 (2003) 8854-8863
38. Li X.-Y., and Fu K.-X. J. Comput. Chem. 25 (2004) 500-509
39. Li X.-Y., Fu K.-X., Zhu Q., and Shan M.-H. J. Comput. Chem. 25 (2004) 835-842
40. Zhu Q., Fu K.-X., Li X.-Y., Gong Z., and Ma J.-Y. J. Comput. Chem. 26 (2005) 399-409
41. PCM-model theory:
42. Tomasi J., and Persico M. Chem. Rev. 94 (1994) 2027-2094
43. Cramer C.J., and Truhlar D.G. Chem. Rev. 99 (1999) 2161-2200
44. Tomasi J., Mennucci B., and Cammi R. Chem. Rev. 105 (2005) 2999-3093
45. Application of PCM-model:
46. Topol I.A., Tawa G.J., Caldwell R.A., Eissenstat M.A., and Burt S.K. J. Phys. Chem. A 104 (2000) 9619-9624
47. Jang Y.H., Sowers L.C., Cagin T., and Goddard III W.A. J. Phys. Chem. A 105 (2001) 274-280
48. Klicic J.J., Friesner R.A., Liu S.-Y., and Guida W.C. J. Phys. Chem. A 106 (2002) 1327-1335
49. Lopez X., Schaefer M., Dejaegere A., and Karplus M. J. Am. Chem. Soc. 124 (2002) 5010-5018
50. Adam K.R. J. Phys. Chem. A 106 (2002) 11963-11972
51. Our previous study:
52. Fu Y., Liu L., Li R.-Q., Liu R., and Guo Q.-X. J. Am. Chem. Soc. 126 (2004) 814-822
53. Li J.-N., Liu L., Fu Y., and Guo Q.-X. Tetrahedron 62 (2006) 4453-4462
54. Li J.-N., Fu Y., Liu L., and Guo Q.-X. Tetrahedron 62 (2006) 11801-11813
55. Parkinson C.J., Mayer P.M., and Radom L. J. Chem. Soc., Perkin Trans. 2 (1999) 2305-2313
56. Henry D.J., Parkinson C.J., Mayer P.M., and Radom L. J. Phys. Chem. A 105 (2001) 6750-6756
57. Song K.-S., Cheng Y.-H., Fu Y., Liu L., and Guo Q.-X. J. Phys. Chem. A 106 (2002) 6651-6658
58. Streitwieser A., Wang D.Z., Stratakis M., Facchetti A., Gareyev R., Abbotto A., Krom J.A., and Kilway K.V. Can. J. Chem. 76 (1998) 765-769
59. +:
60. Reiss H., and Heller A. J. Phys. Chem. 89 (1985) 4207-4213
61. Lim C., Bashford D., and Karplus M. J. Phys. Chem. 95 (1991) 5610-5620
62. Tissandier M.D., Cowen K.A., Feng W.Y., Gundlach E., Cohen M.H., Earhart A.D., Coe J.V., and Tuttle T.R. J. Phys. Chem. A 102 (1998) 7787-7794
63. Lomas J.S., and Vaissermann J. J. Chem. Soc., Perkin Trans. 2 (1998) 1777-1781
64. Manabe S., and Ito Y. J. Am. Chem. Soc. 121 (1999) 9754-9755
65. Matsuzono M., Fukuda T., and Iwao M. Tetrahedron Lett. 42 (2001) 7621-7623
66. Marcantonio K.M., Frey L.F., Murry J.A., and Chen C.-Y. Tetrahedron Lett. 43 (2002) 8845-8848
67. Na J., Houk K.N., and Hilvert D. J. Am. Chem. Soc. 118 (1996) 6462-6471, and references therein.
68. Comins D., and La Munyon D. Tetrahedron Lett. 29 (1988) 773-776
69. Trécourt F., Mallet M., Marsais F., and Quéguiner G. J. Org. Chem. 53 (1988) 1367-1371
70. Comins D., Bavevsky M., and Hong H. J. Am. Chem. Soc. 114 (1992) 10971-10972
71. Kim D.C., Yoo K.H., Kim D.J., Chung B.Y., and Park S.W. Tetrahedron Lett. 40 (1999) 4825-4828
72. Gros P., Fort Y., Queguiner G., and Caubere P. Tetrahedron Lett. 36 (1995) 4791-4794
73. Gros P., Choppin S., and Fort Y. J. Org. Chem. 68 (2003) 2243-2247
74. Fruit C., Turck A., Ple N., Mojovic L., and Queguiner G. Tetrahedron 52 (2002) 2743-2753
75. Hammett L.P. Chem. Rev. 17 (1935) 125-136
76. Hansch C., and Gao H. Chem. Rev. 97 (1997) 2995-3060
77. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., 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., Gonzalez C., and Pople J.A. Gaussian 03, Revision C. 02 (2003), Gaussian, Pittsburgh, PA