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Volumn 282, Issue 5397, 1998, Pages 2247-2250

Atomic contributions to the optical rotation angle as a quantitative probe of molecular chirality

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE;

EID: 0032545216     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.282.5397.2247     Document Type: Article
Times cited : (135)

References (47)
  • 3
    • 0041007379 scopus 로고
    • J. H. van't Hoff, Die Lagerung der Atome im Raume (Vieweg, Braunschweig, Germany, 1894); Arch. Neerl. Sci. Exactes Nat. 9, 455 (1874).
    • (1874) Arch. Neerl. Sci. Exactes Nat. , vol.9 , pp. 455
  • 5
    • 0001750164 scopus 로고
    • P. Walden, Z. Phys. Chem. 15, 196 (1894); K. Freudenberg, J. Todd, R. Seidler, Ann. Chem. 501, 199 (1933).
    • (1894) Z. Phys. Chem. , vol.15 , pp. 196
    • Walden, P.1
  • 9
  • 10
    • 36849110734 scopus 로고
    • J. Applequist, J. Chem. Phys. 58, 4251 (1973); Acc. Chem. Res. 10, 79 (1977).
    • (1977) Acc. Chem. Res. , vol.10 , pp. 79
  • 12
    • 0006086299 scopus 로고
    • Y. H. Pao and D. P. Santry, J. Am. Chem. Soc. 88, 4157 (1966); R. R. Gould and R. Hoffmann, ibid. 92, 1813 (1970); B. K. Satyanarayana and E. S. Stevens, J. Org. Chem. 52, 3170 (1987).
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4157
    • Pao, Y.H.1    Santry, D.P.2
  • 13
    • 0006079359 scopus 로고
    • Y. H. Pao and D. P. Santry, J. Am. Chem. Soc. 88, 4157 (1966); R. R. Gould and R. Hoffmann, ibid. 92, 1813 (1970); B. K. Satyanarayana and E. S. Stevens, J. Org. Chem. 52, 3170 (1987).
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1813
    • Gould, R.R.1    Hoffmann, R.2
  • 14
    • 0343527043 scopus 로고
    • Y. H. Pao and D. P. Santry, J. Am. Chem. Soc. 88, 4157 (1966); R. R. Gould and R. Hoffmann, ibid. 92, 1813 (1970); B. K. Satyanarayana and E. S. Stevens, J. Org. Chem. 52, 3170 (1987).
    • (1987) J. Org. Chem. , vol.52 , pp. 3170
    • Satyanarayana, B.K.1    Stevens, E.S.2
  • 15
    • 0343617393 scopus 로고
    • K. Freudenberg, Ed. Deuticke, Leipzig, Germany
    • W. Kuhn, in Stereochemie, K. Freudenberg, Ed. (Deuticke, Leipzig, Germany, 1933), vol. 8, p. 394; M. Born, Proc. R. Soc. London A 150, 84 (1935).
    • (1933) Stereochemie , vol.8 , pp. 394
    • Kuhn, W.1
  • 16
    • 0343617389 scopus 로고
    • W. Kuhn, in Stereochemie, K. Freudenberg, Ed. (Deuticke, Leipzig, Germany, 1933), vol. 8, p. 394; M. Born, Proc. R. Soc. London A 150, 84 (1935).
    • (1935) Proc. R. Soc. London A , vol.150 , pp. 84
    • Born, M.1
  • 20
    • 0001684860 scopus 로고
    • K. L. Bak et al., Theor. Chim. Acta 90, 441 (1995); A. E. Hansen and T. D. Bouman, J. Am. Chem. Soc. 107, 4828 (1935).
    • (1995) Theor. Chim. Acta , vol.90 , pp. 441
    • Bak, K.L.1
  • 25
    • 0002598521 scopus 로고
    • E. Ruch, W. Runge, G. Kresze, Angew. Chem. Int. Ed. Engl. 12, 30 (1973); E. Ruch, ibid. 16. 65 (1977); Acc. Chem. Res. 5, 49 (1972).
    • (1977) Angew. Chem. Int. Ed. Engl. , vol.16 , pp. 65
    • Ruch, E.1
  • 26
    • 20644471590 scopus 로고
    • E. Ruch, W. Runge, G. Kresze, Angew. Chem. Int. Ed. Engl. 12, 30 (1973); E. Ruch, ibid. 16. 65 (1977); Acc. Chem. Res. 5, 49 (1972).
    • (1972) Acc. Chem. Res. , vol.5 , pp. 49
  • 29
    • 85047696762 scopus 로고    scopus 로고
    • P. L Polavarapu, Tetrahedron Asymmetry 8, 3397 (1997); Mol. Phys. 91, 551 (1997).
    • (1997) Mol. Phys. , vol.91 , pp. 551
  • 38
    • 0001968991 scopus 로고
    • R. D. Amos, Chem. Phys. Lett. 87, 23 (1982); ibid. 124, 376 (1986).
    • (1986) Phys. Lett. , vol.124 , pp. 376
  • 39
    • 11644266970 scopus 로고
    • R. S. Mulliken, J. Chem. Phys. 23, 1833 (1955); ibid. 36, 3428 (1962); J. A. Pople and D. L. Beveridge, Approximate Molecular Orbital Theory (McGraw-Hill, New York, 1970). As in assigning atomic charges, there is some ambiguity in defining atomic contributions to G′. Here, we divide off-diagonal terms equally between participant atoms.
    • (1955) J. Chem. Phys. , vol.23 , pp. 1833
    • Mulliken, R.S.1
  • 40
    • 36849131708 scopus 로고
    • R. S. Mulliken, J. Chem. Phys. 23, 1833 (1955); ibid. 36, 3428 (1962); J. A. Pople and D. L. Beveridge, Approximate Molecular Orbital Theory (McGraw-Hill, New York, 1970). As in assigning atomic charges, there is some ambiguity in defining atomic contributions to G′. Here, we divide off-diagonal terms equally between participant atoms.
    • (1962) J. Chem. Phys. , vol.36 , pp. 3428
  • 41
    • 11644266970 scopus 로고
    • McGraw-Hill, New York
    • R. S. Mulliken, J. Chem. Phys. 23, 1833 (1955); ibid. 36, 3428 (1962); J. A. Pople and D. L. Beveridge, Approximate Molecular Orbital Theory (McGraw-Hill, New York, 1970). As in assigning atomic charges, there is some ambiguity in defining atomic contributions to G′. Here, we divide off-diagonal terms equally between participant atoms.
    • (1970) Approximate Molecular Orbital Theory
    • Pople, J.A.1    Beveridge, D.L.2
  • 43
    • 20644455924 scopus 로고    scopus 로고
    • note
    • The computed specific rotation angle for (R)-2-methyloxirane with the CADPAC program is 24 compared with an experimental value of 14.0, and the computed specific rotation angle for trans-(2R,3R)-dimethyloxirane is 45 compared with an experimental value of 58.8. The computed molar rotation angle for (S)-fluorooxirane is -36.
  • 47
    • 20644456463 scopus 로고    scopus 로고
    • note
    • We thank the PRF (33532AC), NSF (CHE-9727657), and NIH (GM 55433-04) for support of this research and D. W. Pratt for helpful discussions.


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