A comparative study of the scaled vibrational frequencies in the local anesthetics procaine, tetracaine and propoxycaine by means of semiempirical methods: AM1, PM3 and SAM1

Journal of Molecular Structure: THEOCHEM

Volumn 459, Issue 1-3, 1999, Pages 239-271

  Alcolea Palafox, M ^a   Melendez F J ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

AM1; Local anesthetics; PM3; SAM1; Semiempirical methods; Vibrational frequencies

Indexed keywords

PROCAINE; PROPOXYCAINE; TETRACAINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; GEOMETRY; HYDROGEN BOND; VIBRATION;

EID: 0000350140     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00304-2     Document Type: Article

References (56)

1. Foussard-Blanpin O., Quevauviller A. Ann. Pharmaceutiques Francais. 40(2):1982;133.
2. Gupta S.P. Chem. Reviews. 91(6):1991;1109.
3. J.A. Bevan,32+13 J.H. Thompson, Essentials of Pharmacology, Harper and Row, Philadelphia, PA, 1983, p. 202.
4. Wang G.K., Mok W.M., Wang S.-Y. Biophys. J. 67:1994;1851.
5. Alcolea Palafox M. J. Mol. Struct. (Theochem.). 236:1991;161.
6. AMPAC 5.0,32+13 Semichem Inc., 7128 Summit, Shawnee, KS 66216, USA.
7. M.J. Frisch,32+13 G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian 94, Gaussian, Inc., Pittsburgh, PA, 1995.
8. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902.
9. J.J.P. Stewart, J. Comp. Chem. 10(2) (1989) 209, 221.
10. Dewar M.J.S., Jie C., Yu J. Tetrahedron. 49(23):1993;5003.
11. N. Müller, A. Falk, BALL AND STICK Program, Version 2.2r4, Austria, 1981-89.
12. Sinha B.K., Subramanian E., Pattabhi V., Trotter J. Indian J. Pure Appl. Phys. 22:1984;249.
13. Kashino S., Ikeda M., Haisa M. Acta Crystallogr. 38B:1982;1868.
14. Lai T.F., Marsh R.E. Acta Crystallogr. 22:1967;885.
15. Haisa M., Kashino S., Yuasa T., Akigawa K. Acta Crystallogr. 32B:1976;1326.
16. Sinha B.K., Pattabhi V. Proc. Ind. Acad. Sci., Chem. Sci. 98:1987;229.
17. Bruno G., Randaccio L. Acta Crystallogr. 36B:1980;1711.
18. Wang Y., Saebø S., Pittman C.U. J. Mol. Struct. (Theochem.). 281:1993;91.
19. Bludský O., Šponer J., Leszczynski J., Špirko V., Hobza P. J. Chem. Phys. 105(24):1996;11042.
20. Fukuyo M., Hirotsu K., Higuchi T. Acta Crystallogr. 38B(2):1982;640.
21. M. Alcolea Palafox, Spectrochim. Acta 44A(12) (1988) 1465; Rev. Roum. Chim. 34(8) (1989) 1667.
22. M. Alcolea Palafox, Spectrochim. Acta 44A(12) (1988) 1465; Rev. Roum. Chim. 34(8) (1989) 1667.
23. Hamilton J.A., Sabesan M.N. Carbohydr. Res. 102:1982;31.
24. Pletcher J., Sax M., Yoo C.S. Acta Crystallogr. 28B:1972;378.
25. Freeman G.R., Bugg C.E. Acta Crystallogr. 31B:1975;96.
26. Pletcher S.J., Gustaffson B. Acta Crystallogr. 26B:1970;114.
27. Sieiro C., Gonzalez-Diaz P., Smeyers Y.G. J. Mol. Struct. 24:1975;345.
28. Lister D.G., Tyler J.K., Hog J.H., Larsen N.W. J. Mol. Struct. 23:1974;253.
29. Niu Z., Boggs J.E. J. Mol. Struct. (Theochem.). 109:1984;381.
30. Smith D.A., Ulmer II C.W., Gilbert M.J. J. Comput. Chem. 13(5):1992;640.
31. Radhakrishnan T.P., Agranat I. Struct. Chem. 2:1991;107.
32. Quack M., Stockburger M. J. Mol. Spectrosc. 43:1972;87.
33. Pyka J., Kreglewski M. J. Mol. Spectrosc. 109:1985;207.
34. Jiang J.C., Lin C.E. J. Mol. Struct. (Theochem.). 392:1997;181.
35. Gorse A.-D., Pesquer M. J. Mol. Struct. (Theochem.). 281:1993;21.
36. Castellá-Ventura M., Kassab E. Spectrochim. Acta. 50A(1):1994;69.
37. Wilson E.B. Phys. Rev. 45:1934;706.
38. G. Varsanyi, Assignment for Vibrational Spectra of Seven Hundred Benzene Derivatives, Adam Hilger, London, 1974.
39. Goodman L., Ozkabak A.G., Thakur S.N. J. Phys. Chem. 95(23):1991;9044.
40. Sanchez de la Blanca E., Núñez J.L., Martinez P. An. Quim. Ser. A. 82(3):1986;480.
41. M. Alcolea, M. Gil, J.L. Núñez, Vibrational Spectrosc., 6 (1993) 95; Appl. Spectrosc. 48(1) (1994) 22.
42. M. Alcolea, M. Gil, J.L. Núñez, Vibrational Spectrosc., 6 (1993) 95; Appl. Spectrosc. 48(1) (1994) 22.
43. Scherer J.R. Spectrochim. Acta. 19:1963;601.
44. E. Sanchez de la Blanca, Ph.D. Thesis, Madrid, 1986.
45. Alcolea Palafox M. Spectrosc. Letters. 30(8):1997;1495.
46. Alcolea Palafox M. Spectrosc. Letters. 27(5):1994;613.
47. Alcolea Palafox M. Vibrational Spectrosc. 6:1994;149.
48. T. Shimanouchi, Tables of molecular vibrational frequencies, National Standard Reference Data Series, National Bureau of Standards, Washington, DC, 1972.
49. Alcolea Palafox M. J. Mol. Struct. 175:1988;81.
50. R.A. Kydd, P.J. Krueger, J. Chem. Phys. 69(2) (1978) 827.
51. R.A. Kydd, P.J. Krueger, J. Chem. Phys. 72(1) (1980) 280.
52. Kydd R.A., Krueger P.J. Chem. Phys. Lett. 49(3):1977;539.
53. Alcolea Palafox M. Rev. Roum. Chim. 41(3-4):1996;223.
54. Alcolea Palafox M. Indian J. Pure and Appl. Phys. 3(4):1991;5842.
55. Larsen N.W., Hansen E.L., Nicolaisen F.M. Chem. Phys. Letts. 43:1976;584.
56. Healy E.F., Holder A. J. Mol. Struct. (Theochem.). 281:1993;141.