Cotton-Mouton constants for benzoic and phthalic acids

Timosheva, A. P.; Абдуллина, С. Г.; Vul'fson, S. G.; Ermolaeva, L. V.

doi:10.1007/bf00699183

Cited by 2 publications

(2 citation statements)

References 6 publications

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“…7 From direct comparison of K 1 and K 2 , this H-bond was anticipated to be very weak in water, stronger in dimethyl sulfoxide. 32 Conformation of the undissociated acid 5 was investigated in tetrachloromethane on the basis of the experimental dipole moment and the Cotton-Mouton effect 33 with the result that several nonplanar conformers are populated. 34 Even in crystal form, the conformation is unexpected 35 (somewhat distorted nonplanar 5d, Scheme 3).…”

Section: Benzene-12-dicarboxylic Acid (5)mentioning

confidence: 99%

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

et al. 2006

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The structures of ortho-substituted benzoic acids with substituents bearing hydrogen atoms (OH, NH2, COOH and SO2NH2) were investigated by means of IR spectroscopy and of density functional theory at the B3LYP/6-311 + G(d,p) level. All possible conformations, hydrogen bonds, tautomeric forms and zwitterions were taken into consideration and particular attention was given to intramolecular H-bonds and their effect on acidity. Strong H-bonds in the anions of all four acids, were revealed by calculations. In three cases they were confirmed by the IR spectra of the tetrabutylammonium salts in tetrachloromethane solution, while the salt of 1,2-benzenedicarboxylic acid was not sufficiently soluble. The H-bonds are of different strengths but in all cases they are the main cause of the strengthened acidity of these acids in the gas phase and also in solution, although their effect is opposed by weaker H-bonds present in the undissociated acid molecules. The substituent effect on the acidity was evaluated in terms of isodesmic reactions, separately in the acid molecules and in the anions. While the acidity of the 2-OH and 2-NH2 acids is determined essentially by the H-bonds, that of the 2-COOH and 2-SO2NH2 acids is strengthened by the polar effect operating in the undissociated molecule in addition to the H-bond in the anion. The steric inhibition of resonance (SIR), estimated from model conformations with fixed torsional angles, is of little importance. This analysis goes significantly beyond the classical explanation obtained from the acidities in solution but essentially conforms with it.

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Section: Benzene-12-dicarboxylic Acid (5)mentioning

confidence: 99%

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

et al. 2006

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“…This phenomenon is also explained by polarity, and the rules of the likes dissolve each other. According to the literature review, , it was found that the dipole moment of m -TA is greater than that of IPA, and the polarity is positively correlated with the dipole moment. Therefore, the polarity of m -TA is greater than that of IPA.…”

Section: Resultsmentioning

confidence: 99%

Solubility of Isophthalic Acid and m-Toluic Acid in Eight Monobasic Alcohols: Experimental Measurements and Thermodynamic Modeling

et al. 2023

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In this study, the solubility of isophthalic acid (IPA) and m-toluic acid (m-TA) in eight monobasic alcohols, methanol, ethanol, 1-propanol, iso-propanol, 1-butanol, iso-butanol, tertbutanol, and 2-butanol is measured under 101.3 kPa by the method of laser dynamics. The experimental temperature range is 294.35− 360.75 K. The measured data showed that the solubility of IPA and m-toluic acid increased with the increase of temperature in the measured temperature range. At the same temperature, the solubility of m-toluic acid in the same pure solvent is higher than that of IPA. The solubility of IPA and m-toluic acid in eight solvents decreased with the increase of the number of carbon atoms of the solvent. At the same temperature, the solubility ratio of mtoluic acid to IPA in iso-butanol is the highest in the same solvent, and the ratio was greater than 70, making it the best solvent for separating IPA and m-toluic acid. The Apelblat model, the Buchowski−Ksiazczak λh model, and the modified nonrandom two-liquid activity coefficient model were used to correlate the experimental data, and the calculated solubility was in good agreement with the measured result. The calculated solubilities were in good fit with the measured results. The thermodynamic properties were calculated, and the main contributor of the standard molar Gibbs energy of IPA and m-toluic acid in eight alcohols is enthalpy, about 55.40 to 82.86%.

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Cotton-Mouton constants for benzoic and phthalic acids

Cited by 2 publications

References 6 publications

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

Acidity of ortho-substituted benzoic acids: an infrared and theoretical study of the intramolecular hydrogen bonds

Solubility of Isophthalic Acid and m-Toluic Acid in Eight Monobasic Alcohols: Experimental Measurements and Thermodynamic Modeling

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