A theoretical study on N{single bond}H bond dissociation enthalpies of oxo, thio and seleno carbamates and their N-protonated and N-deprotonated species

Journal of Molecular Structure: THEOCHEM

Volumn 858, Issue 1-3, 2008, Pages 94-100

  Kaur, D ^a   Kaur, Rupinder Preet ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Bond dissociation enthalpy; Deprotonation affinities; Electron delocalization; Proton affinities; Spin delocalization

Indexed keywords

EID: 43049113831     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2008.02.019     Document Type: Article

References (47)

1. Olah G.A., Heiner T., Rasul G., and Surya Prakash G.K. J. Org. Chem. 63 (1998) 7793
2. Mindl J., Hrabik O., Sterba V., and Kavalek J. Collect. Czech. Chem. Commun. 65 (2000) 1262
3. Dibenedetto A., Aresta M., Fragale C., and Narracci M. Green Chem. 4 (2002) 439
4. Gupta S.P., Shivarkar A.B., and Chaudhari R.V. J. Chem. Soc., Chem. Commun. (2001) 2620
5. G. Motolesy, M. Nadasy, V. Andriska, Pesticide Chemistry. Academiai Kiado, Budapest, 1988, p. 90.
6. Thonpson A. Pesticide Outlook 13 (2002) 84
7. Lawrence M., Klein D.L., and Nemotho P. Bioorg. Med. Chem. Lett. 7 (1997) 157
8. Greene W.T., and Wuts P.G.M. Protective Groups in Organic Synthesis. second ed. (1991), Wiley, New York pp. 327 and 403
9. Atanasov A.G., Tam S., Rocken J.M., Baker M.E., and Odermatt A. Biochem. Biophys. Res. Commun. 308 (2003) 257
10. Gaudernak E., Seipelt J., Triendl A., Grassauer A., and Kuechler E. J. Virol. 76 (2002) 6004
11. Aradones J., Rodriguez C.L., Corbi A., Arco P.G., Lopez-Cabrera M., Landazuri M.O., and Redondo J.M. J. Biol. Chem. 271 (1996) 10924
12. Schreck R., Grassmann R., Fleckenstein B., and Baeuerle P.A. J. Virol. 66 (1992) 6288
13. Martinez S., Arco P.G., Armeslla A.L., Aramburu J., Luo C., Rao A., and Redondo J.M. Mol. Cell. Biol. 17 (1997) 6437
14. Hellmuth M., Wetzler C., Nold M., Chang J.H., Frank S., Pfeilschifter J., and Muhl H. Carcinogenesis 23 (2002) 1273
15. Oliveira M.R.L., Bellis V.M., and Fernandes N.G. Struct. Chem. 8 (1997) 205
16. Koketsu M., Ishida M., Takakuro N., and Ishihara H. J. Org. Chem. 67 (2002) 486
17. Takahashi H., Nishina A., Fukumoto R., Kimura H., Koketsu M., and Ishihara H. Eur. J. Pharm. Sci. 24 (2004) 291
18. Lin G., Cheng Liao W., and Ku Z.H. Protein J. 24 (2005) 201
19. Lin G., Liu Y.C., Wu Y.G., and Lee Y.R. J. Phys. Org. Chem. 17 (2004) 707
20. Lin G. J. Chin. Chem. Soc. 51 (2004) 423
21. Steenken S. Chem. Rev. 89 (1989) 503
22. Stubbe J., and van der Donk W.A. Chem. Rev. 98 (1998) 705
23. Stadtman E.R. Annu. Rev. Biochem. 62 (1993) 797
24. Easton C.J. Chem. Rev. 97 (1997) 53
25. Steenken S. Biol. Chem. 378 (1997) 477
26. Boyd S.L., Boyd R.J., Bessonette P.W., Kerdraon D.I., and Aucoin N.T. J. Am. Chem. Soc. 117 (1995) 8816
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, Jr., J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.11.2, Gaussian, Inc., Pittsburgh, PA, 2001.
28. Curtiss L.A., Raghavachari K., and Pople J.A. J. Chem. Phys. 98 (1993) 1293
29. McMillen D.F., and Golden D.M. Annu. Rev. Phys. Chem. 33 (1982) 493
30. Burk P., Koppel I.A., Rummel A., and Trummal A. J. Phys. Chem. A. 104 (2000) 1602
31. Chandra A.K., Nam P.C., and Nguyen M.T. J. Phys. Chem. A. 107 (2003) 9182
32. Kaur D., and Kaur R.P. J. Mol. Struct. (Theochem) 757 (2005) 53
33. DiLabio G.A., Pratt D.A., LoFaro A.D., and Wright J.S. J. Phys. Chem. A. 103 (1999) 16502
34. Chandra A.K., and Uchimaru T. Int. J. Mol. Sci. 3 (2002) 407
35. DiLabio G.A., LoFaro A.D., and Wright J.S. J. Phys. Chem. A. 103 (1999) 1653
36. Pratt D.A., Wright J.S., and Ingold K.U. J. Am. Chem. Soc. 121 (1999) 4877
37. Sinha P., Boesch S.E., Gu C., Wheeler R.A., and Wilson A.G. J. Phys. Chem. A. 108 (2004) 9213
38. McQurrie D.A. Statistical Mechanics (1976), Harper and Row, New York
39. Scott A.P., and Radom L. J. Phys. Chem. A. 100 (1996) 16502
40. Jursic B.S., and Martin R.M. Int. J. Quantum Chem. 59 (1996) 495
41. Pople J.A., Gordon M.H., Fox D.J., Raghavchari K., and Curtiss L.A. J. Chem. Phys. 10 (1989) 5622
42. Remko M., and Rode B.M. J. Phys. Chem A. 103 (1999) 431
43. Kaur D., Kaur R.P., and Kaur P. Bull. Chem. Soc. Jpn. 79 (2006) 1869
44. Liu W.Z., and Bordwell F.G. J. Org. Chem. 61 (1996) 4778
45. Bordwell F.G., Harrelson Jr. J.A., and Lynch T.Y. J. Org. Chem. 55 (1990) 3337
46. Bordwell F.G., and Ji G.Z. J. Am. Chem. Soc. 113 (1991) 8398
47. Kaur D., Sharma P., Bharatam P.V., and Dogra N. J. Mol. Struct. (Theochem) 759 (2006) 41