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1,8-Diphenyl- and 1,8-dipyridylnaphthalenes are known to undergo fast rotation about the two aryl-aryl bonds at room temperature. In general, the enantiomeric anti-isomers of these triaryls rapidly interconvert via the thermodynamically less stable meso syn-intermediate with a rotational energy barrier of 60-75 kJ/mol. See. Wolf C. (Ed), RSC, Cambridge
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1,8-Diphenyl- and 1,8-dipyridylnaphthalenes are known to undergo fast rotation about the two aryl-aryl bonds at room temperature. In general, the enantiomeric anti-isomers of these triaryls rapidly interconvert via the thermodynamically less stable meso syn-intermediate with a rotational energy barrier of 60-75 kJ/mol. See. In: Wolf C. (Ed). Dynamic Stereochemistry of Chiral Compounds (2008), RSC, Cambridge 84-94
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note
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Crystallographic data of 1 have been deposited with the Cambridge Crystallographic Data Center (CCDC 765565). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, United Kingdom (fax: 44 1223 336033 or email: deposit@ccdc.cam.ac.uk).
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note
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All attempts to obtain a crystal structure of the amino acid-derived diimines have been unsuccessful.
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47
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33947292077
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Based on the basicity of salicylidenimines, we expect that the imine groups are protonated prior to the formation of free carboxylic acid groups. See:
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Based on the basicity of salicylidenimines, we expect that the imine groups are protonated prior to the formation of free carboxylic acid groups. See:. Leach B.E., and Leussing D.L. J. Am. Chem. Soc. 93 (1971) 3377
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Leach, B.E.1
Leussing, D.L.2
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