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Neuvonen H, Neuvonen K, Pasanen P. Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents. J Org Chem. 2004;69(11):3794-800doi: 10.1021/jo035521u.
Neuvonen, H., Neuvonen, K., & Pasanen, P. (2004). Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents. The Journal of organic chemistry, 69(11), 3794-800. https://doi.org/10.1021/jo035521u
Neuvonen, Helmi, et al. "Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents." The Journal of organic chemistry vol. 69,11 (2004): 3794-800. doi: https://doi.org/10.1021/jo035521u
Neuvonen H, Neuvonen K, Pasanen P. Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents. J Org Chem. 2004 May 28;69(11):3794-800. doi: 10.1021/jo035521u. PMID: 15153011.
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J Org Chem. 2004 May 28;69(11):3794-800. doi: 10.1021/jo035521u.

Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents.

The Journal of organic chemistry

Helmi Neuvonen, Kari Neuvonen, Paavo Pasanen

Affiliations

  1. Department of Chemistry, University of Turku, FIN-20014 Turku, Finland. [email protected]

PMID: 15153011 DOI: 10.1021/jo035521u

Abstract

Carbonyl carbon (13)C NMR chemical shifts delta(C)(C[double bond]O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C(6)H(4)CO(2)C(6)H(4)-p-X (X = NO(2), CN, Cl, Br, H, Me, or MeO; Y = NO(2), Cl, H, Me, MeO, or NMe(2) ) have been used as a tool to study substituent effects on the carbonyl unit. The goal of the work was to study the cross-interaction between X and Y in that respect. Both the phenyl substituents X and the benzoyl substituents Y have a reverse effect on delta(C)(C[double bond]O). Electron-withdrawing substituents cause shielding while electron-donating ones have an opposite influence, with both inductive and resonance effects being significant. The presence of cross-interaction between X and Y could be clearly verified. Electronic effects of the remote aromatic ring substituents systematically modify the sensitivity of the C[double bond]O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of delta(C)(C[double bond]O) to the substitution of another ring, while electron-donating substituents inversely affect the sensitivity. It is suggested that the results can be explained by substituent-sensitive balance of the contributions of different resonance structures (electron delocalization, Scheme 1).

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