Substituent effects on gas-phase acidities of formic acid and its silicon and sulphur derivatives R - M(= X)XH(M = C, Si; X = O, S; R = H, F, Cl, OH, NH2 and CH3)

Molecular Physics

Volumn 98, Issue 11, 2000, Pages 709-714

  Remko, Milan ^a   Smieško, Martin ^a   Van Duijnen, Piet Th ^b  

^a Faculty of Natural Sciences   (Slovakia)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CARBOXYLIC ACIDS; COMPOSITION EFFECTS; SILICON; SUBSTITUTION REACTIONS; SULFUR;

FORMIC ACID; GAS PHASE ACIDITY; MOLECULAR ORBITAL;

MOLECULAR PHYSICS;

EID: 0034630780     PISSN: 00268976     EISSN: None     Source Type: Journal    
DOI: 10.1080/002689700162054     Document Type: Article

References (53)

1. Falbe, J. (ed.), 1985, Methoden der Organischen Chemie, Vol. E5, 5th Edn (Stuttgart: Georg Thieme Publishers).
2. Solomons, T. W., 1996, Organic Chemistry, 6th Edn (New York: Wiley).
3. Voet, D., and Voet, J. G., 1995, Biochemistry, 2nd Edn (New York: Wiley).
4. Cumming, J. B., and Kebarle, P., 1978, Can. J. Chem., 56, 1.
5. Bartmess, J. E., and McIver Jr, R. T., 1979. Gas Phase Ion Chemistry, Vol. 2, edited by M. T. Bowers (New York: Academic Press).
6. Lias, S. G., Bartmess, J. E., Liebman, J. L., Holmes, R. D., Lewis, W. G., and Mallard, W. G., 1988, J. phys. Chem. Ref. Data, 17, Suppl. 1.
7. Hunter, E. P., and Lias, S. G., 1998, J. phys. Chem. Ref. Data, 27, 413; (http://webbook.nist.gov/chemistry/).
8. Wiedmann, F. A., and Wesdemiotis, Ch., 1994, J. Am. chem. Soc., 116, 2481.
9. Zhang, X., Gross, U., and Seppelt, K., 1995, Angew. Chem. Int. Ed. Engl., 34, 1858.
10. Withnall, R., and Andrews, L., 1985, J. phys. Chem., 89, 3261.
11. Withnall, R., and Andrews, L., 1985, J. Am. chem. Soc., 107, 2567.
12. Chmielecka, J., Chojnowski, J., Eaborn, C., and Stancyk, W. A., 1987, J. chem. Soc. Chem. Commun., 1337.
13. Patyk, A., Sander, W., Gauss, J., and Cremer, D., 1989, Angew. Chem. Int. Ed., 28, 898.
14. Damrauer, R., and Hankin, J. A., 1995, Chem. Rev., 95, 1137.
15. Engler, R., and Gattow, G., 1972, Z. Anorg. Allg. Chem., 388, 78.
16. Randhawa, H. S., and Rao, C. N. R., 1974, J. molec. Struct., 21, 123.
17. Randhawa, H. S., Walter, W., and Meese, C. O., 1977, J. molec. Struct., 37, 187.
18. Hocking, W. H., and Winnewisser, G., 1976, Z. Naturforsch., 31a, 422.
19. Hocking, W. H., and Winnewisser, G., 1977, Z. Naturforsch., 32a, 1108.
20. Winnewiser, B. P., and Hocking, W. H., 1980. J. phys. Chem., 84, 1771.
21. Fausto, R., Batista de Carvalho, L. A. E., Teixeira-Dias, J. J. C., and Ramos, N., 1989. J. chem. Soc. Faraday Trans. 2, 85, 1945.
22. Smith, B. J., and Radom, L., 1991. J. phys. Chem., 95, 10549.
23. Bagno, A., and Scorrano, G., 1996, J. phys. Chem., 100, 1535, 1545.
24. Merrill, G. N., and Kass, S. R., 1996, J. phys. Chem., 100, 17465.
25. Remko, M., Liedl, K. R., and Rode, B. M., 1996, Chem. Phys. Lett., 263, 379.
26. Wiberg, K. B., and Laidig, K. E., 1987, J. Am. chem. Soc., 109, 5935.
27. Siggel, M. R. F., Streitwieser Jr. A., and Thomas, T. D., 1988, J. Am. chem. Soc., 110, 8022.
28. Wiberg, K. B., 1990, J. Am. chem. Soc., 112, 4177.
29. Darling, C. L., and Schlegel, H. B., 1993. J. phys. Chem., 97, 8207.
30. De Proft, F., Amira, S., Choho, K., and Geerlings, P., 1994. J. phys. Chem., 98, 5227.
31. Ji, D., and Thomas, T. D., 1994. J. phys. Chem., 98, 4301.
32. Hiberty, P. C., and Byrman, C. P., 1995. J. Am. chem. Soc., 117, 9895.
33. Wiberg, K. B., Ochterski, J., and Streitwieser, A., 1996, J. Am. chem. Soc., 118, 8291.
34. Remko, M., Liedl, K. R., and Rode, B. M., 1997, J. molec. Struct. Theochem, 418, 179.
35. Remko, M., and VanDuijnen, P. T., 1999, Chem. Phys. Lett., 308, 242.
36. Remko, M., 1999, Molec. Phys., 96, 1677.
37. Nyden, N. R., and Peterson, G. A., 1981, J. chem. Phys., 75, 1843.
38. Peterson, G. A., and Al-Laham, M. A., 1991, J. chem. Phys., 94, 6081, 6091.
39. Montgomery, J. A., Ochterski, J. W., and Petersson, G. A., 1994. J. chem. Phys., 101, 5900.
40. Petersson, G. A., Tensfeldt, T., and Montgomery, J. A., 1991. J. chem. Phys., 94, 6091.
41. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery Jr. J. A., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Stefanoy, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Andres, J. L., Gonzales, C., Head-Gordon, M., Replogle, E. S., and Pople, J. A., 1998, Gaussian 98, Revision A.7 (Pittsburgh PA Gaussian, Inc.).
42. Politzer, P., Huheey, J. E., Murray, J. S., and Grodzicki, M., 1992, J. molec. Struct. Theochem, 259, 99.
43. Hocking, W. H., 1976, Z. Naturforsch., 31a, 1113.
44. Caldwell, G., Renneborg, R., and Kebarle, P., 1989, Can. J. Chem., 67, 611.
45. Bowser, J. D., 1993, Inorganic Chemistry (Belmont, California: Wadsworth Inc.).
46. Damoun, S., Langenaeker, W., Van de Woude, G., and Geerlings, P., 1995, J. phys. Chem., 99, 12151.
47. Geerlings, P., De Proft, F., and Langenaeker, W., 1999, Adv. Q. Chem., 33, 303.
48. Kapp, J., Remko, M., and Schleyer, P. V. R., 1996, J. Am. chem. Soc., 118, 5745.
49. Remko, M., 1997, Molec. Phys., 91, 929.
50. Kudo, J., and Nagase, S., 1985, J. Am. chem. Soc., 107, 2589.
51. Remko, M., Liedl, K. R., and Rode, B. M., 1998, J. phys. Chem., 102, 771.
52. Remko, M., Lyne, P. D., and Richards, G. W., 1999, Phys. Chem. Chem. Phys., 1, 5353.
53. Ochterski, J. W., Petersson, G. A., and Wiberg, K., 1995, J. Am. chem. Soc., 117, 11299.