Parabolic Relationship between the Basicity of the Nucleophile and π-Face Selection in Addition of the Substituted Acetylide Ions to Cyclohexanone and Cyclohexanethione

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 521-530

  Cieplak, Andrzej Stanislaw ^a,b  

^a YALE UNIVERSITY   (United States)

^b STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007742055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713722     Document Type: Article

References (80)

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27. 3) 3.26, 0.0, 0.85 and 2.25, 0.0, 0.33; CN 1.41, 2.53, 0.0 and 1.15, 2.61, 0.0 (Cieplak, A. S.; Wiberg, K. B.; Ochterski, J. W. Unpublished results.). See also: Wong, S. S.; Paddon-Row, M. N. J. Chem. Soc., Chem. Commun. 1990, 456; 1991, 327, and ref 12b. Let us also add that the 6-31G* Mulliken charges were found to be linearly related to other measures of atomic charge for this basis set. This is not true for the 6-31+G* and other basis sets: Wiberg, K. B.; Rablen, P. J. Comput. Chem. 1993, 14, 1504.
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