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Paper | Regular issue | Vol 60, No. 12, 2003, pp.2685-2705
Published online, 2nd October, 2003
DOI: 10.3987/COM-03-9889
Nuclear Magnetic Resonance Spectroscopical Studies of 2-Carbonyl Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices

Kyu Ok Jeon, Ji Sook Yu, and Chang Kiu Lee*

*Department of Chemistry, Kangwon National University, Chuncheon 200-701, Korea

Abstract

1H And 13C chemical shifts of formyl, acetyl, benzoyl, and methoxycarbonyl derivatives of benzene, thiophene, pyrrole and furan in chloroform-d, methanol-d4, and DMSO-d6 are examined. Deviation of the signals of the ring protons and carbonyl carbons provide bases for estimating the indices of aromaticity of the heterocycles. The exceptionally large carbonyl stretching vibration of furan derivatives and correlations of the stretching frequencies with the reactivities of the carbonyl groups are discussed.