Journal of the American Chemical Society p. 3608 - 3613 (1986)
Update date:2022-08-04
Topics:
Crossley, Maxwell J.
Harding, Margaret M.
Sternhell, Sever
β-Substitution of 5,10,15,20-tetraphenylporphyrin alters the position of the tautomeric equilibrium 2a <*> 2b, which can be observed by high-field variable-temperature NMR spectroscopy.When R= NO2, CHO, Cl, Br, OMe, CN, NHCOMe,SPh, OCOPh, or OH the dominant tautomer is 2a, where R lies on the isolated double bond, while when R= CH=CH2, CH2OH, NH2, Me, CH(Me)2, or (CH2)3Me the major tautomer is 2b, where R lies on the aromatic delocalization pathway.These substituent effects do not follow a know scale.
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