Saccharin: A combined experimental and computational thermochemical investigation of a sweetener and sulfonamide

Molecular Physics

Volumn 103, Issue 2-3, 2005, Pages 221-228

  Matos, M Agostinha R ^a   Miranda, Margarida S ^a   Morais, Victor M F ^a   Liebman, Joel F ^b  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL ANALYSIS; COMBUSTION; COMPUTATIONAL METHODS; CRYSTALLINE MATERIALS; DERIVATIVES; ENTHALPY; SUBLIMATION;

DENSITY FUNCTIONAL THEORY; MOLAR ENTHALPY; SACCHARIN; SWEETENER;

SUGARS;

EID: 27744511501     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268970512331316175     Document Type: Article

References (45)

1. W.N. Hubbard, D.W. Scott, G. Waddington, In Experimental Thermochemistry, Vol. 1, F.D. Rossini (Ed.), Chapter 5, Interscience, New York (1956).
2. F.D. Rossini, In Experimental Thermochemistry, Vol. 1, F.D. Rossini (Ed.), Chapter 14, Interscience, New York (1956).
3. CODATA, J. Chem. Thermodyn., 10, 903 (1978).
4. D.D. Wagman, W.H. Evans, V.B. Parker, R.H. Schumm, I. Halow, S.M. Bailey, K.L. Churney, R.L. Nuttall, The NBS Tables of Chemical Thermodynamic Properties, J. Phys. Chem. Ref. Data, 11, Supplement no 2 (1982).
5. The admittedly sparse thermochemistry of sulfonamides and other sulfonic acid derivatives is reviewed by J.F. Liebman, In The Chemistry of the Sulphonic Acids, Esters and their Derivatives, S. Patai, Z. Rappoport (Eds), Chapter 8, John Wiley & Sons, Chichester (1991)
6. and updated soon thereafter in a more general overview of organosulfur thermochemistry by J.F. Liebman, K.S.K. Crawford, S.W. Slayden, In The Chemistry of Functional Groups Supplement S: The Chemistry of Sulphur-containing Functional Groups, S. Patai, Z. Rappoport (Eds), Chapter 4, John Wiley & Sons, Chichester (1993). The more precise references are:
7. [5a] Z.V. Pushkareva, Z.U. Kokoshko, Zh. Obshch. Khim., 16, 1269 (1946).
8. [5b] H. Yan, F. Zhang, P. Juang, R. Hu, Kexue Tongbao, 17(5), 278 (1982).
9. (CA 96:169803g (1982).) We note with admitted distress that the Chemical Abstract source fails to give the correct enthalpy of formation for this species nor for the two ring methylated derivatives that accompany it, and the original paper has a typographical error in the enthalpy of combustion found by averaging the individual measurements also included.
10. [6a] V.M.F. Morais, M.S. Miranda, M.A.R. Matos, J.F. Liebman, Mol. Phys., 102, 525 (2004).
11. [6b] M.A.R. Matos, M.S. Miranda, V.M.F. Morais, J.F. Liebman, Org. Biomol. Chem., 1, 2566 (2003).
12. A. Charlton, J.I. Macnab, Thermochim. Acta, 344, 15 (2000).
13. J.B. Pedley, R.D. Naylor, S.P. Kirby, Thermochemical Data of Organic Compounds, 2nd edn, Chapman & Hall, New York (1986).
14. R.C. Weast (Ed.), Handbook of Chemistry and Physics, 70th edn, CRC Press, Cleveland, OH (1989-1990).
15. C. Plato, A.R. Glasgow Jr., Anal. Chem., 41, 330 (1969).
16. R. Sabbah, Xu-wu An, J.S. Chickos, M.L.P. Leitão, M.V. Roux, L.A. Torres, Thermochim. Acta, 331, 93 (1999).
17. M.A.V. Ribeiro da Silva, M.L.C.C.H. Ferrão, A.J.M. Lopes, J. Chem. Thermodyn., 25, 229 (1993).
18. M.A.V. Ribeiro da Silva, M.L.C.C.H. Ferrão, F. Jiye. J. Chem. Thermodyn., 26, 839 (1994).
19. W.D. Good, D.W. Scott, G. Waddington, J. Phys. Chem., 60, 1080 (1956).
20. G. Waddington, S. Sunner, W.N. Hubbard, In Experimental Thermochemistry, Vol. 1, F.D. Rossini (Ed.), Chapter 7, Interscience, New York (1956).
21. H.A. Skinner, A. Snelson, Trans. Faraday Soc., 56, 1776 (1960).
22. J. Coops, R.S. Jessup, K. Van Nes, Experimental Thermochemistry, Vol. 1, F.D. Rossini (Ed.), Chapter 3, Interscience, New York (1956).
23. A.I. Vogel, Quantitative Inorganic Analysis, Longman, London (1978).
24. F.A. Adedeji, D.L.S. Brown, J.A. Connor, M.L. Leung, I.M. Paz-Andrade, H.A. Skinner, J. Organomet. Chem., 97, 221 (1975).
25. D.R. Stull, E.F. Westrum, G.C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York (1969).
26. The following Calvet and Knudsen measurements were made at 421 K for 2,3-dichloro and 2,3,6,7-tetrachloroquinoxaline where nearly identical values were found for the two techniques.
27. [21a] V.M.F. Morais, M.S. Miranda, M.A.R. Matos, J. Chem. Thermodyn., 36, 377 (2004).
28. [21b] M.J.S. Monte, D.M. Hillesheim, J. Chem. Eng. Data, 45, 1088 (2000).
29. A.D. Becke, J. Chem. Phys., 98, 5648 (1993).
30. C.T. Lee, W.T. Yang, R.G. Parr, Phys. Rev. B, 37, 785 (1998).
31. P.C. Hariharan, J.A. Pople, Theoret. Chim. Acta, 28, 213 (1973).
32. P.A. Scott, L. Radom, J. Chem. Phys., 100, 16502 (1996).
33. T.H. Dunning Jr., J. Chem. Phys., 90, 1007 (1989);
34. D.E. Woon, T.H. Dunning Jr., J. Chem. Phys., 98, 1358 (1993);
35. D.E. Woon, T.H. Dunning Jr., J. Chem. Phys., 100, 2975 (1994);
36. A.K. Wilson, D.E. Woon, K.A. Peterson, T.H. Dunning Jr., J. Chem. Phys., 110, 7667 (1999).
37. GAMESS-UK is a package of ab initio programs written by M.F. Guest, J.H. van Lenthe, J. Kendrick, K. Schoffel, and P. Sherwood, with contributions from R.D. Amos, R.J. Buenker, H.J. J. van Dam, M. Dupuis, N.C. Handy, I.H. Hillier, P.J. Knowles, V. Bonacic-Koutecky, W. von Niessen, R.J. Harrison, A.P. Rendell, V.R. Saunders, A.J. Stone, A.H. de Vries.
38. The package is derived from the original GAMESS code due to M. Dupuis, D. Spangler and J. Wendoloski, NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS) 1980.
39. The DFT module within GAMESS-UK was developed by Dr P. Young under the auspices of EPSRC's Collaborative Computacional Project No. 1 (CCP1) (1995-1997).
40. J.F. Liebman, E.H. Mørkved, Struct. Chem., 6, 207 (1995).
41. Indenones interpolate the conveniently stable fluorenones, with the well-established enthalpy of formation of the parent ketone, cf. R. Sabbah, L. El Watik, C. Minadakis, C. R. Acad. Sci. Paris, 307, 239 (1998), and cyclopentadienones for which the literature thermochemical citations and data therein seemingly do not allow any additional understanding.
42. The first study involves the dimerization of 2,5-dialykyl-3,4- diphenylcyclopentadienones, c.f. H.M. Weiss, J. Chem. Soc. Perkin Trans. 2, 439 (1991). While reaction enthalpies are given, we are unable to adequately estimate the enthalpy of formation of the highly functionalized methanoindanone products in order to derive the enthalpy of formation of the desired cyclopentadienone monomers.
43. -1, cf. B.V. Lebedev, T.G. Kilagina, N.N. Smirnova, Z.V. Shifrina, M.S. Averina, A.L. Rusanov, J. Thermal Anal. Calor., 74, 735 (2003). However, we are doubtful of the applicability of any available estimaton approach for the necessary enthalpy of sublimation to use this datum.
44. M.V. Roux, P. Jiménez, M.A. Martin-Luengo, J.Z. Dávalos, Z. Sun, R.S. Hosmane, J.F. Liebman, J. Org. Chem., 62, 2732 (1997).
45. S. Nuritdinov, I.V. Numanov, I.M. Nasvrov, Dokl. Akad. Nauk. Tadzh, 72, 34 (1973). See the disclaimers given for the values from this reference by Liebman, Crawford and Slayden [5].