13C n.m.r. studies. X. 13C spectra of some substituted methyl benzoates

1967 ◽  
Vol 45 (3) ◽  
pp. 233-238 ◽  
Author(s):  
K. S. Dhami ◽  
J. B. Stothers
Keyword(s):  
Aromatic Ring ◽  
Chemical Shifts ◽  
Methyl Esters ◽  
Benzoic Acids ◽  
Similar Series ◽  
Substituted Benzoic Acids

The 13C spectra of the methyl esters of 20 substituted benzoic acids have been recorded, and the chemical shifts of the carbon nuclei of the carbomethoxyl group and aromatic ring have been measured. These shielding results are discussed and compared with the corresponding data for similar series of acetophenones and anisoles. Some evidence of steric inhibition of conjugation is presented for certain diortho-substituted examples.

Correction. Methyl Esters of Substituted Benzoic Acids

1952 ◽  
Vol 74 (24) ◽  
pp. 6319-6319
Author(s):  
Robert West ◽  
Severo Ornstein ◽  
Donald McKee ◽  
Robert Layzer
Keyword(s):  
Methyl Esters ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids

scholarly journals Influence of ortho substituents on 17O NMR chemical shifts in phenyl esters of substituted benzoic acids

2010 ◽  
Vol 24 (7) ◽  
pp. 539-552 ◽  
Author(s):  
Vilve Nummert ◽  
Vahur Mäemets ◽  
Mare Piirsalu ◽  
Ilmar A. Koppel
Keyword(s):  
Chemical Shifts ◽  
Benzoic Acids ◽  
17O Nmr ◽  
Nmr Chemical Shifts ◽  
Substituted Benzoic Acids

Ab initio calculations on 4-substituted benzoic acids; a further theoretical investigation into the nature of substituent effects in aromatic derivatives

1977 ◽  
Vol 55 (9) ◽  
pp. 1567-1574 ◽  
Author(s):  
Paul G. Mezey ◽  
William F. Reynolds
Keyword(s):  
Ab Initio ◽  
Field Effect ◽  
Chemical Shifts ◽  
Substituent Effects ◽  
Electron System ◽  
Acid Dissociation ◽  
Molecular Orbital Calculations ◽  
Atomic Charges ◽  
Benzoic Acids ◽  
Substituted Benzoic Acids

Ab initio (STO-3G) molecular orbital calculations for 4-substituted benzoic acids and XCH3–HCO2H pairs are used to derive a theoretical field, TF and resonance, TR(BA), substituent scale. Comparison with previous calculations for 4-substituted styrenes shows that a common field scale can be used for different systems but that different resonance scales are necessary, depending upon the electronic nature of the probe group. The field effect primarily reflects the direct electrostatic interaction between the substituent and the carboxylic acid. However, there are also significant contributions due to field-induced polarization of the intervening phenyl π electron system. By contrast, the π polarization effect seems to be the dominant field effect in the case of non-interacting probes (such as carbon atomic charges or chemical shifts). A very close parallel is noted between substituent effects upon atomic charges and acid dissociation energies.

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