Thermochemical study of the cyanophenol isomers

Structural Chemistry

Volumn 15, Issue 2, 2004, Pages 103-116

  Matos, M A R ^a   Miranda, M S ^a   Morais, V M F ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Combustion; Cyanophenols; Enthalpy; Sublimation; Theoretical calculations; Thermochemistry

Indexed keywords

2 CYANOPHENOL; 3 CYANOPHENOL; 4 CYANOPHENOL; ANION; OXIDE; OXYGEN; PHENOL DERIVATIVE; PHENOXIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; COMBUSTION; DENSITY FUNCTIONAL THEORY; ENTHALPY; GAS; GEOMETRY; HYDROGEN BOND; ISOMER; MICROCALORIMETRY; STANDARD; THERMAL ANALYSIS;

EID: 3543070087     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:STUC.0000011245.91971.c1     Document Type: Article

References (48)

1. Ribeiro da Silva, M. A. V.; Morais, V. M. F.; Matos, M. A. R.; Miranda, M. S. J. Org. Chem. 1999, 64, 8816.
2. Borges dos Santos, R. M.; Martinho Simões, J. A. J. Phys. Ref. Chem. Data 1998, 27, 707.
3. Handbook of Chemistry and Physics, 70th ed.; Weast, R. C.; Ed. CRC Press Cleveland, Ohio, 1989-1990.
4. Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Pilcher, G. Rev. Port. Quím. 1984, 26, 163; Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Pilcher, G. J. Chem. Thermodyn. 1984, 16, 1149.
5. Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Pilcher, G. Rev. Port. Quím. 1984, 26, 163; Ribeiro da Silva, M. A. V.; Ribeiro da Silva, M. D. M. C.; Pilcher, G. J. Chem. Thermodyn. 1984, 16, 1149.
6. Coops, J.; Jessup, R. S.; Van Nes, K. Experimental Thermochemistry; Rossini, F. D., Ed.; Wiley (Interscience): New York, 1956; Vol. 1, Chap. 3.
7. The NBS Tables of Chemical Thermodynamic Properties J. Phys. Chem. Ref. Data. 1982, 11, Suppl. 2.
8. Skinner, H. A.; Snelson, A. Trans. Faraday Soc. 1960, 56, 1776.
9. Washburn, E. W. J. Res. Nat. Bur. St. 1933, 10, 525.
10. Hubbard, W. N.; Scott, D. W.; Waddington, G. Experimental Thermochemistry; Rossini, F. D., Ed.; Wiley (Interscience): New York, 1956; Vol. 1, Chap. 5.
11. I.U.P.A.C. J. Phys. Chem. Ref. Data 1997, 26, 1239.
12. Adedeji, F. A.; Brown, D. L. S; Connor, J. A.; Leung, M.; Paz-Andrade, M. I.; Skinner, H. A. J. Organomet. Chem. 1975, 97, 221.
13. Stull, D. R.; Westrum, E. F.; Sinke, G. C. The Chemical Thermodynamics of Organic Compounds: Wiley: New York, 1969.
14. Rossini, F. D. Experimental Thermochemistry: Rossini F. D., Ed., Wiley (Interscience): New York, 1956; Vol. 1, Chap. 14, pp. 297-320.
15. CODATA J. Chem. Thermodyn. 1978, 10, 903.
16. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Amer. Chem. Soc. 1980, 102, 939; Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Pietro, W. J.; Hehre, W. J. J. Amer. Chem. Soc. 1982, 104, 2797.
17. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Amer. Chem. Soc. 1980, 102, 939; Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Pietro, W. J.; Hehre, W. J. J. Amer. Chem. Soc. 1982, 104, 2797.
18. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217; Francl, M. M.; Pietro, W. J; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
19. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217; Francl, M. M.; Pietro, W. J; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
20. Becke, A. D. Phys. Rev. 1988, A38, 3098.
21. Perdew, J. PPhys. Rev. 1986, B33, 6622.
22. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
23. Huzinaga, S. Ed., Gaussian Basis Sets for Molecular Calculations: Elsevier: New York, 1984.
24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
25. Dupuis, M.; Spangler, D.; Wendoloski, J. J. NRCC Software Catalog: Program QG10, 1980; Schimdt, M. W.; Boatz, J. A.; Baldridge, K. K.; Koseki, S.; Gordon, M. S.; Elbert, S. T.; Lam, B. QCPE Bull. 1987, 7, 115.
26. Dupuis, M.; Spangler, D.; Wendoloski, J. J. NRCC Software Catalog: Program QG10, 1980; Schimdt, M. W.; Boatz, J. A.; Baldridge, K. K.; Koseki, S.; Gordon, M. S.; Elbert, S. T.; Lam, B. QCPE Bull. 1987, 7, 115.
27. UK-GAMESS is a package of ab initio programs written by Guest, M. F.; van Lenthe, J. H.; Kendrick, J.; Schoffel, K. and Sherwood, P. with contributions from Amos, R. D.; Buenker, R. J.; van Dam, H. J. J.; Dupuis, M.; Handy, N. C; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; von Niessen, W.; Harrison, R. J.; Rendell, A. P.; Saunders, V. R.; Stone, A. J. and de Vries A. H. The package is derived from the original GAMESS code, Dupuis, M.; Spangler, D.; Wendoloski, J. NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980. The DFT module within GAMESS-UK was developed by Dr. P. Young under the auspices of EPSRC's Collaborative Computational Project No. 1 (CCP1) (1995-1997).
28. St-Amant, A.; Salahub, D. R. Chem. Phys. Lett. 1990, 169, 387; St-Amant, A. Ph. D. Thesis, Université de Montréal, 1992.
29. St-Amant, A.; Salahub, D. R. Chem. Phys. Lett. 1990, 169, 387; St-Amant, A. Ph. D. Thesis, Université de Montréal, 1992.
30. Cabral, B. J. C.; Fonseca, R. G. B.; Simões, J. A. M. Chem. Phys. Lett. 1996, 258, 436.
31. Carlson, G. L.; Fateley, W. G. J. Phys. Chem. 1973, 77, 1157.
32. Radom, L.; Hehre, W. J.; Pople, J. A.; Carlson, G. L.; Fateley, W. G. J. Chem. Soc. Chem. Commun. 1972, p. 308.
33. Larsen, N. W. J. Mol. Struct. 1979, 51, 175.
34. Hagen, K.; Hedberg, K. Chem. Phys. 1973, 59, 158.
35. Pedley, J. B. Thermochemical Data and Structures of Organic Compounds: Vol. I, Thermodynamics Research Center, College Station, Texas, 1994.
36. An, X.; Mansson, M. J. Chem. Thermodyn. 1983, 15, 287.
37. Matos, M. A. R.; Miranda, M. S.; Morais, V. M. F. J. Phys. Chem. A. 2000, 104, 9260.
38. Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Amer. Chem. Soc. 1989, 111, 1423; Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Amer. Chem. Soc. 1989, 111, 4594.
39. Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Amer. Chem. Soc. 1989, 111, 1423; Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Amer. Chem. Soc. 1989, 111, 4594.
40. Pross, A.; Radom, L.; Taft, R. W. J. Org. Chem. 1980, 45, 818.
41. Wu, Y.; Lai, D. K. W. J. Org. Chem. 1996, 61, 7904.
42. Bader, R. W. F.; Carroll, M. T.; Cheeseman, J. R.; Chang, C. J. Amer. Chem. Soc. 1987, 109, 7968.
43. Bader, R. W. F.; Slee, T. S.; Cremer, D.; Kraka, E. J. Amer. Chem. Soc. 1983, 105, 5061.
44. Foster, J. P.; Weinhold, F. J. Amer. Chem. Soc., 1980, 102, 7211; Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
45. Foster, J. P.; Weinhold, F. J. Amer. Chem. Soc., 1980, 102, 7211; Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
46. Fujio, M.; McIver, Jr. R. T.; Taft, R. W. J. Amer. Chem. Soc. 1981, 103, 4017.
47. McMahon, T. B.; Kebarle, P. J. Amer. Chem. Soc. 1977, 99, 2222.
48. Cumming, J. B.; Kebarle, P. Can. J. Chem. 1978, 56, 1.