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Nuclear magnetic resonance (NMR) studies of acid-induced conformational switching (trans/cis isomerization) of N,N-diarylamides bearing a pyridine moiety indicated that the trans/cis conformational preference of these amides is dependent on the relative π-electron densities of the two N-aromatic parts, and can be controlled by protonation or deprotonation of pyridine.
We have investigated acid- and base-induced conformational alterations of N-aryl-N-troponyl amides containing an electron-donating group on the phenyl ring. NMR spectral studies indicated that the E/Z conformational preferences of these amides can be reversibly controlled by pH-dependent protonation or deprotonation of the tropolone moiety. Thus, these compounds have potential applications as acid/base-controllable...
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