13C nuclear magnetic resonance spectroscopy of 6- and 7-substituted coumarins. Correlation with hammett constants

Hugo E. Gottlieb; Roberto Alves De Lima; Franco Delle Monache

doi:10.1039/P29790000435

¹³C nuclear magnetic resonance spectroscopy of 6- and 7-substituted coumarins. Correlation with hammett constants

Hugo E. Gottlieb
, Roberto Alves De Lima
, Franco Delle Monache

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

Abstract

The ¹³C n.m.r. spectra of coumarin and 19 6- and 7-substituted derivatives thereof have been obtained and fully assigned. The chemical shifts of the αβ-unsaturated lactone system have been correlated with Hammett constants: C-3 was found to fit very well with σ⁺, and carbons 2 and 4 with σ. A satisfactory fit was found for the two ring-junction carbons with σ_p⁺, but not with σ_m or σ_m⁺. The electronic implications of these relationships are discussed.

Original language	English
Pages (from-to)	435-437
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	4
DOIs	https://doi.org/10.1039/P29790000435
State	Published - 1979
Externally published	Yes

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abstract = "The 13C n.m.r. spectra of coumarin and 19 6- and 7-substituted derivatives thereof have been obtained and fully assigned. The chemical shifts of the αβ-unsaturated lactone system have been correlated with Hammett constants: C-3 was found to fit very well with σ+, and carbons 2 and 4 with σ. A satisfactory fit was found for the two ring-junction carbons with σp+, but not with σm or σm+. The electronic implications of these relationships are discussed.",

author = "Gottlieb, \{Hugo E.\} and \{De Lima\}, \{Roberto Alves\} and Monache, \{Franco Delle\}",

year = "1979",

doi = "10.1039/P29790000435",

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journal = "Journal of the Chemical Society, Perkin Transactions 2",

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T1 - 13C nuclear magnetic resonance spectroscopy of 6- and 7-substituted coumarins. Correlation with hammett constants

AU - Gottlieb, Hugo E.

AU - De Lima, Roberto Alves

AU - Monache, Franco Delle

PY - 1979

Y1 - 1979

N2 - The 13C n.m.r. spectra of coumarin and 19 6- and 7-substituted derivatives thereof have been obtained and fully assigned. The chemical shifts of the αβ-unsaturated lactone system have been correlated with Hammett constants: C-3 was found to fit very well with σ+, and carbons 2 and 4 with σ. A satisfactory fit was found for the two ring-junction carbons with σp+, but not with σm or σm+. The electronic implications of these relationships are discussed.

AB - The 13C n.m.r. spectra of coumarin and 19 6- and 7-substituted derivatives thereof have been obtained and fully assigned. The chemical shifts of the αβ-unsaturated lactone system have been correlated with Hammett constants: C-3 was found to fit very well with σ+, and carbons 2 and 4 with σ. A satisfactory fit was found for the two ring-junction carbons with σp+, but not with σm or σm+. The electronic implications of these relationships are discussed.

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JO - Journal of the Chemical Society, Perkin Transactions 2

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IS - 4

ER -

¹³C nuclear magnetic resonance spectroscopy of 6- and 7-substituted coumarins. Correlation with hammett constants

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