15024-07-4Relevant academic research and scientific papers
Intramolecular charge transfer dual fluorescence of substituted-phenyl p-dimethylaminobenzoates with comparable electron acceptors
Huang, Wei,Zhang, Xuan,Li-Hua, Ma.,Wang, Chao-Jie,Jiang, Yun-Bao
, p. 401 - 407 (2002)
A series of substituted-phenyl p-dimethylaminobenzoates with para- or meta-substitution at the ester phenyl ring (p-OH, p-CH3, H, p-Br, m-Cl, and p-NO2) were synthesized and their fluorescence spectra were recorded. Intramolecular ch
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
Neuvonen, Helmi,Neuvonen, Kari,Pasanen, Paavo
, p. 3794 - 3800 (2007/10/03)
Carbonyl carbon 13C NMR chemical shifts δC(C=O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C 6H4CO2C6H4-p-X (X = NO2, CN, Cl, Br, H, Me, or MeO; Y = NO2, Cl, H, Me, MeO, or NMe2) 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 δC(C=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=O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of δC(C=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).
