AIM interpretation of strain energy of oxiranes

Chemical Physics

Volumn 287, Issue 1-2, 2003, Pages 125-135

  Vila, Antonio ^a   Mosquera, Ricardo A ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

AIM theory; Oxiranes; Strain energy

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; HYDROCARBON;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; ELECTRON; ENERGY; NOMENCLATURE; THEORY;

EID: 0037305612     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0301-0104(02)00984-9     Document Type: Article

References (55)

1. K.B. Wiberg, Angew. Chem. Int. Ed. Engl. 25 (1986) 312.
2. J.F. Liebman, A. Greenberg, Chem. Rev. 76 (1976) 311.
3. A. Greenberg, J.F. Liebman, Strained Organic Compounds, Academic Press, New York, 1978.
4. N.L. Allinger, U. Burkert, Molecular Mechanics, American Chemical Society, Washington, DC, 1982.
5. S.W. Benson, J.H. Buss, J. Chem. Phys. 29 (1958) 546.
6. J.L. Franklin, Ind. Eng. Chem. 41 (1949) 1070.
7. K.B. Wiberg, J. Comput. Chem. 5 (1984) 197.
8. W.J. Hehre, R. Ditchfield, L. Radom, J.A. Pople, J. Am. Chem. Soc. 92 (1970) 4796.
9. P. George, M. Trachtman, C.W. Bock, A.M. Brett, Tetrahedron 32 (1976) 317.
10. B.A. Hess, L.J. Schaad, J. Am. Chem. Soc. 105 (1983) 7500.
11. C. Blahous III, H.F. Schaefer III, J. Phys. Chem. 92 (1988) 959.
12. R.F.W. Bader, in: Atoms in Molecules, A Quantum Theory, International Series of Monographs in Chemistry, 22, Oxford University Press, Oxford, 1990.
13. R.F.W. Bader, Chem. Rev. 91 (1991) 893.
14. K. Wiberg, R.F.W. Bader, C.D.H. Lau, J. Am. Chem. Soc. 109 (1987) 1001.
15. D. Cremer, E. Kraka, J. Am. Chem. Soc. 107 (1985) 3811.
16. D. Cremer, E. Kraka, J. Am. Chem. Soc. (1985) 3800.
17. S.M. Bachrach, J. Phys. Chem. 93 (1989) 7780.
18. S.M. Bachrach, J. Phys. Chem. 97 (1993) 4996.
19. S. Grimme, J. Am. Chem. Soc. 118 (1996) 1529.
20. A.M. Graña, R.A. Mosquera, J. Chem. Phys. 110 (1999) 6606.
21. A.M. Graña, R.A. Mosquera, J. Chem. Phys. 113 (2000) 1492.
22. A. Vila, E. Carballo, R.A. Mosquera, Can. J. Chem. 78 (2000) 1535.
23. L.A. Paquette (Ed.), Handbook of Reagents for Organic Synthesis, Wiley, Chichester, 1999.
24. S.M. Bachrach, A. Streitweiser, J. Comput. Chem. 10 (1989) 514.
25. J.A. Boatz, M. Gordon, J. Phys. Chem. 93 (1989) 3025.
26. C. Lian, L.C. Allen, J. Am. Chem. Soc. 113 (1991) 1878.
27. P.K. Bose, T.M. Black, P.L. Polavarapu, Chem. Phys. 139 (1989) 409.
28. P. George, C.W. Bock, J.P. Glusker, J. Phys. Chem. 96 (1992) 3702.
29. J. Catalán, M. Yañez, J. Am. Chem. Soc. 100 (1978) 1398.
30. O. Mó, J.L.G. De Paz, M. Yañez, J. Phys. Chem. 91 (1987) 6484.
31. D.H. Aue, H.M. Webb, W.R. Davidson, M. Vidal, M.T. Bowers, H. Goldwhite, L.E. Vertal, J.E. Douglas, P.A. Kollman, G.L. Kenyon, J. Am. Chem. Soc. 102 (1980) 5151.
32. R.F.W. Bader, Phys. Rev. B 49 (1994) 13348.
33. R.F.W. Bader, P.L.A. Popelier, T.A. Keith, Angew. Chem. Int. Ed. Engl. 33 (1994) 620.
34. M.J. Frisch et al., GAUSSIAN 94, Revision C.3, Gaussian Inc., Pittsburgh, PA, 1995.
35. M.W. Wong, Chem. Phys. Lett. 256 (1996) 391.
36. MORPHY98, A topological analysis program written by P.L.A. Popelier with a contribution from R.G.A. Bone (UMIST, Engl., EU).
37. P.L.A. Popelier, Chem. Phys. Lett. 288 (1994) 160.
38. AIMPAC: A suite of programs for the Theory of Atoms in Molecules; R.F.W. Bader and coworkers (Eds.), McMaster University, Hamilton, Ont., Canada L8S 4M1. Contact bader@mcmail.cis.mcmaster.ca.
39. T. Dudev, C. Lim, J. Am. Chem. Soc. 120 (1988) 4450.
40. N.L. Allinger, M.T. Tribble, M.A. Miller, D.W. Wertz, J. Am. Chem. Soc. 93 (1971) 1637.
41. E.M. Engler, J.B. Andose, P.v.R. Schleyer, J. Am. Chem. Soc. 95 (1973) 8005.
42. E.P. Hunter, S.G. Lias, in: W. Mallard, P.J. Linstrom (Eds.), Protton Affinity Evaluations, NIST Chemistry Webbok, NIST Standard Reference Database Number 69, March (1998), National Institute of Standards and Technology, Gaithersburg, MD 20899 (http://webbook.nist.gov).
43. J. Cioslowski, M. Schimeczek, G. Liu, V. Stoyanov, J. Chem. Phys. 113 (2000) 9377.
44. A.M. Graña, M. Mandado, A. Vila, R.A. Mosquera, J. Cioslowski, J. Comput. Chem. (submitted).
45. L. Lorenzo, R.A. Mosquera, Chem. Phys. Lett. 356 (2002) 305.
46. A. Vila, R.A. Mosquera, Tetrahedron 57 (2001) 9415.
47. J.D. Cox, G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, 1970.
48. H.K. Eigenmann, D.M. Golden, S.W. Benson, J. Phys. Chem. 77 (1973) 1687.
49. M.W. Chase Jr., Termochemical Tables, fourth ed., J. Phys. Chem. Ref. Data, Monograph 9 (1998) 1.
50. According to one of the referees of this paper, Eqs. (8)-(10) are ill-defined homodesmotic processes. Eq. (7) is the only one that implicitly matches all the requirements imposed by George et al.'s definition [9]. Eq. (7) uses group increments, whereas Eqs. (8) and (9) use a group-bond contribution and Eq. (9) could be regarded as an incomplete bond scheme. Nevertheless, in our opinion, Eqs. (7)-(12) verify all the conditions explicitly imposed in that definition of homodesmotic processes.
51. M. Alcamí, O. Mó, M. Yáñez, J. Comput. Chem. 19 (1998) 1072.
52. D.V. Vechten, J.F. Liebman, Isr. J. Chem. 21 (1981) 105.
53. J.F. Liebman, D.V. Vechten, in: J.F. Liebman, A. Greenberg (Eds.), Molecular Structure and Energetics: Physical Measurements, vol. 2, VCH, Deerfield Beach, FL, New York, 1987.
54. A. Vila, R.A. Mosquera, Chem. Phys. Lett. 345 (2001) 445.
55. A. Vila, R.A. Mosquera, J. Chem. Phys. 115 (2001) 1264.