Polarography of non-benzenoid aromatic and related substances—VI: Polarographic and spectrophotometric study of steric hindrance of coplanarity in 3-Phenylsydnone (cas 120-06-9)s☆

Add time:09/02/2019    Source:sciencedirect.com

Substitution of alkyl groups on the ortho-position of 3-phenylsydnone causes a steric hindrance in coplanarity of the sydnone and phenyl rings. This was proved from the shift of the polarographic half-wave potentials (in excess of the polar effects), from the ultra-violet spectra, and from scale models. The behaviour of 3-o-tolylsydnone resembles more that of 3-benzylsydnone than that of 3-phenylsydnone. In 3′,4′-dihydroquinolino[1′,2′-c]-sydnone, the —CH2 CH2—bridge brings the sydnone and phenyl rings into a nearly coplanar position, shown on scale models, and its polarographic and spectrophotometric behaviour resembles that of 3-phenylsydnone.

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