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Volumn 119, Issue 32, 1997, Pages 7545-7549

A density functional study of 2-lithio-1,3-dithiane and 2-lithio-2-phenyl-1,3-dithiane: Conformational preference of the C-Li bond and structural analysis

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DITHIANE DERIVATIVE; LITHIUM DERIVATIVE; ORGANOLITHIUM COMPOUND;

EID: 0030878921     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9703943     Document Type: Article
Times cited : (42)

References (31)
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    • Lee, C.1    Yang, W.2    Parr, R.G.3
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    • 0004025315 scopus 로고
    • Theoretical Chemistry Institute, University of Wisconsin: Madison, WI
    • NBO 4.0. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
    • (1994) NBO 4.0
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    • NBO 4.0. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
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    • Reed, E.A.1    Weinstock, R.B.2    Weinhold, F.J.3
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    • NBO 4.0. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 1994. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 735. Reed, E. A.; Weinhold, F. J. J. Chem. Phys. 1985, 83, 1736. Reed, E. A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 83, 735.
    • (1985) J. Chem. Phys. , vol.83 , pp. 1736
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    • note
    • Of course, solvation may be particularly important for studying the real organolithium species. For example, the ΔS of solvated lithio derivatives of 2-phenyl-1,3-dithiane for the axial ⇌ equatorial equilibrium should not be zero. Conformations favoring intramolecular chelation would also require the displacement of one or two solvent molecules by the sulfur atoms and is expected to be entropically favorable.
  • 23
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    • note
    • Nevertheless, Hartree-Fock minimal basis set calculations consistently estimate the barriers either too high or low. Part of the success of the DFT can be attributed to correlational effects.


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