The solvatochromic comparison method. 6. The .pi.* scale of solvent polarities

Kamlet, Mortimer J.; Abboud, José‐Luis M.; Taft, Robert W.

doi:10.1021/ja00460a031

Cited by 1,582 publications

(955 citation statements)

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“…Examples of such solubility-related parameters include thermodynamic solubility parameter of Hildebrand, 1 and solvatochromic parameters. [2][3][4][5][6][7][8] A set of solvatochromic parameters was originally derived from spectroscopic methods of investigating the intermolecular interactions by Abraham in 1970-1980. [2][3][4][5] The parameters included solvent polarity/polarizability scale, solvent basicity scale, and solvent acidity scale, which were then used in QSPR models to estimate properties and activities of solvents or solutes in the solutions.…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5][6][7][8] A set of solvatochromic parameters was originally derived from spectroscopic methods of investigating the intermolecular interactions by Abraham in 1970-1980. [2][3][4][5] The parameters included solvent polarity/polarizability scale, solvent basicity scale, and solvent acidity scale, which were then used in QSPR models to estimate properties and activities of solvents or solutes in the solutions. [2][3][4][5] The parameter set was later extended to the corresponding solute descriptors of hydrogen-bonding acidity (A) and basicity (B) scales, and polarity/polarizability (S) scale.…”

Section: Introductionmentioning

confidence: 99%

“…7 The approach for measuring these parameters is similar to those of Kamlet and Taft,2,3 where a probe with specific interactions with solvent has been used and variances in spectroscopy data have been recorded and applied for the definition of the solvent scales. [2][3][4]8,[20][21][22][23] In formulating the independent solvent scales, the choice of an appropriate probe for the experimental determination of the scales is the major challenge. The selected probe should measure the effect of a single solvent property, for example, hydrogen-bonding basicity, without the interference of any other solvent effects.…”

Section: Introductionmentioning

confidence: 99%

“…2-5 The parameters included solvent polarity/polarizability scale, solvent basicity scale, and solvent acidity scale, which were then used in QSPR models to estimate properties and activities of solvents or solutes in the solutions. [2][3][4][5] The parameter set was later extended to the corresponding solute descriptors of hydrogen-bonding acidity (A) and basicity (B) scales, and polarity/polarizability (S) scale. 9,10 In addition to these parameters, the general solvation equation proposed by Abraham and co-workers 9,10 (equation 1) also includes excess molar refraction (E) and the one percent of McGowan molar volume (V).…”

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QSPR Modeling using Catalan Solvent and Solute Parameters

Jouyban¹,

Fakhree²,

Shayanfar³

et al. 2011

J. Braz. Chem. Soc.

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A área de correlação quantitativa entre estrutura e propriedade (QSPR) pode beneficiar-se de descritores moleculares que representam interações intermoleculares. Catalan desenvolveu um método de escalas solvatocrômicas para solventes que pode ser explorado para esta finalidade. Neste trabalho, escalas de solvente de Catalan foram usadas como descritores moleculares para o desenvolvimento de modelos QSPR, e para o cálculo de novos descritores de soluto para uso posterior em QSPR. As escalas Catalan para o solvente e os descritores de soluto derivados foram recentemente comparados com o método de descritores de Abraham, em termos da qualidade do QSPR desenvolvido. Os parâmetros Catalan para solventes, que mostraram uma correlação modesta com os correspondentes descritores de Abraham, mostraram-se bem sucedidos para modelar temperatura de fusão, temperatura de ebulição, ponto de ignição, índice de refração, tensão superficial, densidade e parâmetro de solubilidade dos solventes, com médias geométricas dos desvios relativos (GMRD) de 7,1, 6,6, 4,9, 3,8, 9,1, 6,0 e 4,2%, respectivamente. Os descritores do soluto foram obtidos a partir das equações de regressão entre a solubilidade de um soluto em diferentes solventes com um GMRD total de 30,0%. Os descritores de soluto obtidos desta maneira superam o modelo de solvatação geral de Abraham no cálculo de solubilidade em meio aquoso de 27 solutos de várias famílias químicas. Os descritores Catalan podem ser considerados como um recurso valioso para modelagem QSPR.The field of quantitative structure-property relationship (QSPR) can greatly benefit from molecular descriptors that particularly represent the intermolecular interactions. Catalan has developed a set of solvatochromic scales for solvents, which could be exploited for this purpose. In this work, Catalan solvent scales were explored as molecular descriptors for the development of QSPR models, and for the calculation of new solute descriptors for further use in QSPR. Catalan solvent scales and the newly derived solute descriptors were compared with the commonly used set of Abraham descriptors in terms of the quality of the developed QSPRs. Catalan solvent parameters, which showed modest correlation with the corresponding Abraham descriptors, proved to be successful in modeling melting point, boiling point, flash point, refractive index, surface tension, density, and solubility parameter of the solvents with geometric mean relative deviations (GMRD) of 7. 1, 6.6, 4.9, 3.8, 9.1, 6.0, and 4.2%, respectively. The solute descriptors were obtained from regression equations between a solute's solubility in different solvents with an overall GMRD of 30.0%. The solute descriptors obtained in this way outperformed Abraham general solvation model in the calculation of aqueous solubility for 27 solutes of broad chemical ranges. It was concluded that Catalan descriptors can be regarded as a valuable resource for QSPR modeling.Keywords: Catalan, solvatochromic, solubility, modeling, QSPR Jouyban et al. 685 Vol. 22, No. 4, 20...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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QSPR Modeling using Catalan Solvent and Solute Parameters

Jouyban¹,

Fakhree²,

Shayanfar³

et al. 2011

J. Braz. Chem. Soc.

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“…Kamlet-Taft parameters 20 in combination with linear free energy relationships (LFER) have been previously used to model solute-solvent interactions by describing solvents in terms of hydrogen bond donation (a), hydrogen bond acceptance (b), and polarizability (p*). We applied this strategy to reveal the extent of solute/solvent interaction for ABFL using specific Kamlet-Taft parameters from a similar electronic system (see ESIw).…”

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‘Lock and key’ control of optical properties in a push–pull system

et al. 2008

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Separation and identification of peptide mixtures in a synthesis crude of carbetocin by liquid chromatography/electrospray ionization mass spectrometry

Sanz‐Nebot

Toro

Garces

et al. 1999

Rapid Commun. Mass Spectrom.

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In order to separate and characterize the target peptide and the side-product peptide compounds of a synthesis crude of the peptide hormone carbetocin, liquid chromatography coupled to high-flow electrospray ionization mass spectrometry (LC/eS-MS) has been used. Carbetocin is an important drug with recognized therapeutical application for stimulation of uterine contractions to facilitate parturition. Stepwise solid phase peptide synthesis (SPPS) commonly results in unwanted side products associated with incomplete peptide chains. Consequently, this procedure requires extensive purification and characterization of the final synthesis crude. The linear solvation energy relationship (LSER) method has been applied to optimize the proportion of organic modifier of the mobile phase used in the established LC method. On the other hand, ES-MS has allowed rapid and reliable identification of the target peptide and the other impurities present in the carbetocin synthesis products.

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The solvatochromic comparison method. 6. The .pi.* scale of solvent polarities

Cited by 1,582 publications

References 11 publications

QSPR Modeling using Catalan Solvent and Solute Parameters

QSPR Modeling using Catalan Solvent and Solute Parameters

‘Lock and key’ control of optical properties in a push–pull system

Separation and identification of peptide mixtures in a synthesis crude of carbetocin by liquid chromatography/electrospray ionization mass spectrometry

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