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Carbon‐13 nuclear magnetic resonance spectra of some methyl and phenyl substituted 2 H ‐azirines
Author(s) -
Isomura Kazuaki,
Taniguchi Hiroshi,
Mishima Masaaki,
Fujio Mizue,
Tsuno Yuho
Publication year - 1977
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270091002
Subject(s) - azirine , substituent , chemical shift , ring (chemistry) , chemistry , benzene , spectral line , carbon 13 , aziridine , resonance (particle physics) , carbon fibers , stereochemistry , crystallography , organic chemistry , physics , materials science , atomic physics , composite number , quantum mechanics , astronomy , composite material
Carbon‐13 n.m.r. spectra have been obtained for some methyl and phenyl substituted 2 H ‐azirines. The higher field resonance of C‐2 than that of the corresponding aziridine carbon is interpreted in terms of ring strain. Substituent effects on the chemical shifts of the azirine ring carbons are discussed. A set of additivity parameters for the methyl and phenyl groups are obtained which can be used for the calculation of the chemical shifts of the azirine ring carbons. The substituent effect of an azirine ring on the chemical shift of benzene is also discussed in comparison with those of some other substituents. A high degree of s character (48.5%) in the exocyclic orbital of C‐3 is indicated by a large J ( 13 C‐3,H) value (242.5 Hz).