Characteristic Integrated Intensities of Bands in the Infrared Spectra of Carboxylic Acids<sup>1</sup>

Wenograd, Joseph; Spurr, Robert A.

doi:10.1021/ja01579a002

Cited by 76 publications

(26 citation statements)

References 1 publication

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“…Computational calculations are useful to predict positions of the vibrational IR transitions and to help define these ambiguous assignments. For instance, our data reveal that the experimental band at 3260 cm −1 is more likely to correspond to the lactamic N-H stretching, supporting the assignments done by Yang et al and Ferraro et al 32,33 As can be seen in Table III (compare UCB values against free γ -lactam, pyrrole and propionic acid values), 35,[37][38][39] hydrogen bonding in UCB causes a redshift of all the stretching bands of the groups involved in the interaction.…”

Section: Infrared Vibrational Frequencies and Hydrogen Bonding Enesupporting

confidence: 90%

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Vega-Hissi

Estrada

Lavecchia

et al. 2013

The Journal of Chemical Physics

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The pKa, the negative logarithm of the acid dissociation equilibrium constant, of the carboxylic acid groups of unconjugated bilirubin in water is a discussed issue because there are quite different experimental values reported. Using quantum mechanical calculations we have studied the conformational behavior of unconjugated bilirubin species (in gas phase and in solution modeled implicitly and explicitly) to provide evidence that may clarify pKa values because of its pathophysiological relevance. Our results show that rotation of carboxylate group, which is not restricted, settles it in a suitable place to establish stronger interactions that stabilizes the monoanion and the dianion to be properly solvated, demonstrating that the rationalization used to justify the high pKa values of unconjugated bilirubin is inappropriate. Furthermore, low unconjugated bilirubin (UCB) pKa values were estimated from a linear regression analysis.

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Section: Infrared Vibrational Frequencies and Hydrogen Bonding Enesupporting

confidence: 90%

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Vega-Hissi

Estrada

Lavecchia

et al. 2013

The Journal of Chemical Physics

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“…In non-polar solution such as CC14 [47] and C6H 6 [48] dimerization constants of alkyl carboxylic acids are almost independent of the chain length of the alkyl residue. The results have been elucidated in terms of a cyclic dimer where nonpolar groups hardly "see" each other.…”

Section: Dimer Formation Of Carboxylic Acid In Aqueous Systemmentioning

confidence: 99%

Aqueous molecular clusters isolated as liquid fragments by adiabatic expansion of liquid jets

Nishi

1990

Z Phys D - Atoms, Molecules and Clusters

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A new approach to solution chemistry and cluster physics has been developed by combining molecular beam mass-spectrometry with liquid jet expansion method. Many features characteristic of molecular association in aqueous solution were observed in the cluster mass spectra and some of them showed good agreement with reported values of euthalpy changes and entropy changes for molecular association-dissociation equilibria in liquid phase. Although it lacks persuadable theoretical analysis at this stage, several new findings obtained by this technique are introduced to appeal its potentialities of physical analysis of solution systems at molecular levels.

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“…The dimerization constants determined from the infrared absorption are much larger than those determined from the liquid-liquid distribution data.1, [13][14][15] The salting-out effect for acetic acid in aqueous electrolyte solutions has been studied by Rothmund and Wilsmore,16) by …”

Section: Discussionmentioning

confidence: 99%

Studies of Liquid-Liquid Partition Systems. V. The Formation of Mixed Dimers with Two Carboxylic Acids in Carbon Tetrachloride

Sekine¹,

Isayama²,

Yamaguchi³

et al. 1967

Bulletin of the Chemical Society of Japan

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The distribution of acetic, propionic and butyric acids, or of mixtures of two of these acids, between carbon tetrachloride and aqueous solutions has been studied at 25°C. The distribution data have been explained in terms of the partition of the acid monomer molecules and the dimerization of the monomer molecules in the organic phase. A salting-out effect has been observed upon additions of sodium perchlorate to the aqueous phase; this salting-out effect is larger in the order butyric>propionic>acetic acid. From the distribution data, the equilibrium constants for the distribution and the dimerization have been determined, and the formation constants for the mixed-dimer molecules have been compared with the statistical values. It has been concluded that the mixed-dimer molecules are equally stable or only a little less stable than had been statistically expected.

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Characteristic Integrated Intensities of Bands in the Infrared Spectra of Carboxylic Acids¹

Cited by 76 publications

References 1 publication

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Aqueous molecular clusters isolated as liquid fragments by adiabatic expansion of liquid jets

Studies of Liquid-Liquid Partition Systems. V. The Formation of Mixed Dimers with Two Carboxylic Acids in Carbon Tetrachloride

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Characteristic Integrated Intensities of Bands in the Infrared Spectra of Carboxylic Acids1

Cited by 76 publications

References 1 publication

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Computational chemical analysis of unconjugated bilirubin anions and insights into pKa values clarification

Aqueous molecular clusters isolated as liquid fragments by adiabatic expansion of liquid jets

Studies of Liquid-Liquid Partition Systems. V. The Formation of Mixed Dimers with Two Carboxylic Acids in Carbon Tetrachloride

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Characteristic Integrated Intensities of Bands in the Infrared Spectra of Carboxylic Acids¹