Restricted Rotation in Benzamidinium Systems

Journal of Organic Chemistry

Volumn 37, Issue 25, 1972, Pages 4173-4178

  McKennis, J S ^a   Smith, P A S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003704554     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00798a045     Document Type: Article

References (27)

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13. Although the use of approximative methods can in some cases lead to considerable error [A. Allerhand, et al., J. Amer. Chem. Soc., 88, 3185 (1966) 3, the barriers obtained here correlate well with both those in the literature and those calculated using a more exact rate equation (Allerhand, et al.).
14. Recently, the validity of using approximate equations for determining Kc has been discussed [D. Kost, E. H. Carlson, and M. Raban, Chem. Commun., 656 (1971)].
15. J. Sandström [J. Phys. Chem., 71, 2318 (1967) 1 using MO methods has calculated the delocalization energy in a positively charged amidinium system to be 0.632β.
16. R. Kwok and P. Pranc [J. Org. Chem., 32, 738 (1967)] have concluded from ambient.-temperature spectra that the positive charge in the hydrochloride of N-ethyl-N'-methyl-N'-phenylbenzainidine is localized on the nitrogen bearing the ethyl and phenyl groups. However, a fixed conformation about the C-NHCH3 bond would be consistent with their data.
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