QSPR Models for the Molar Refraction, Polarizability and Refractive Index of Aliphatic Carboxylic Acids Using the ZEP Topological Index

Berinde, Zoiţa

doi:10.3390/sym13122359

Cited by 8 publications

(3 citation statements)

References 20 publications

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“…In case of the 1‐n‐alkanols, however, this correlation is clearly worse (R 2 =0.879), [12] in particular because of methanol and ethanol. In contrast, for the 1‐carboxylic acids the correlation is somewhat better (R 2 =0.933), [13] but the relationship obviously has a negative slope which does definitely not fit to the theories presented.…”

Section: Introductionmentioning

confidence: 67%

Understanding Refractive Index Changes in Homologous Series of Unbranched Organic Compounds Based on Beer's Law

Mayerhöfer

Spange

2023

ChemPhysChem

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Changes of the refractive index for homologous series of hydrocarbons are usually plotted versus the density. While there is a clear linear dependence for alkanes and alkenes, the linearity deteriorates for homologous series with functional groups involving heteroatoms. The slope can even become negative, e. g., for carboxylic acids. For gaining a deeper understanding and to establish a more general correlation, we reinvestigate the corresponding theories starting with the Newton‐Laplace, Gladstone‐Dale and the Lorentz‐Lorenz rules. We revisit the concept of molar refractivity pioneered by Landolt and Brühl and show that it is closely connected with a twin of Beer's law. We conclude that the refractive index of homologues series should better be plotted versus the molar concentration of the main UV‐chromophore, the C−H bond, which actually causes the refractive index changes. This new approach is not limited to alkanes and alkenes but holds for homologous series with functional groups including heteroatoms.

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Section: Introductionmentioning

confidence: 67%

Understanding Refractive Index Changes in Homologous Series of Unbranched Organic Compounds Based on Beer's Law

Mayerhöfer

Spange

2023

ChemPhysChem

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“…This revealed strong and significant correlations for the log P , van der Waals surface area, polarizability, van der Waals volume, and associated molar refractivity. Inclusion of the structurally unrelated QX-314, however (Figure C), showed a low correlation for the log P as a measure of the hydrophobicity (Figure A,B), while the van der Waals volume and the more sophisticated molar refraction and polarizability , were still strongly correlated with a higher potency. Given the correlation of polarizability, molar refraction, and van der Waals volume among each other (Figure S7) for the given set of data, the size of the BPC is likely the driving descriptor.…”

Section: Resultsmentioning

confidence: 99%

Symmetrical Bispyridinium Compounds Act as Open Channel Blockers of Cation-Selective Ion Channels

Haufe,

Loser,

Danker

et al. 2024

ACS Pharmacol. Transl. Sci.

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Current treatments against organophosphate poisoning (OPP) do not directly address effects mediated by the overstimulation of nicotinic acetylcholine receptors (nAChR). Non-oxime bispyridinium compounds (BPC) promote acetylcholine esterase-independent recovery of organophosphate-induced paralysis. Here, we test the hypothesis that they act by positive modulatory action on nAChRs. Using two-electrode voltage clamp analysis in combination with mutagenesis and molecular docking analysis, the potency and molecular mode of action of a series of nine BPCs was investigated on human α7 and muscle-type nAChRs expressed in Xenopus laevis oocytes. The investigated BPCs inhibited α7 and/or muscle-type nAChRs with IC 50 values in the high nanomolar to high micromolar range. Further analysis of the most potent analogues revealed a noncompetitive, voltagedependent inhibition. Co-application with the α7-selective positive allosteric modulator PNU120596 and generation of α7/5HT3 receptor chimeras excluded direct interaction with the PNU120596 binding site and binding to the extracellular domain of the α7 nAChR, suggesting that they act as open channel blockers (OCBs). Molecular docking supported by mutagenesis localized the BPC binding area in the outer channel vestibule between the extracellular and transmembrane domains. Analysis of BPC action on other cation-selective channels suggests a rather nonspecific inhibition of pentameric cation channels. BPCs have been shown to ameliorate organophosphate-induced paralysis in vitro and in vivo. Our data support molecular action as OCBs at α7 and muscle-type nAChRs and suggest that their positive physiological effects are more complex than anticipated and require further investigation.

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“…Within the last ca. 85 years, many papers have been published producing the refractive indices and densities to characterize various hydrocarbons , alcohols [35][36][37][38][39][40][41][42], ethers [43-47], acids [48],…”

Section: Sources Of Refractivity and Polarizability Datamentioning

confidence: 99%

Revision and Extension of a Generally Applicable Group-Additivity Method for the Calculation of the Refractivity and Polarizability of Organic Molecules

Naef¹,

Acree²

2022

Preprint

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In a continuation and extension of an earlier publication, the calculation of the refractivity and polarizability of organic molecules at standard conditions is presented, applying a commonly applicable computer algorithm based on an atom-group additivity method, where the molecules are broken down into their constituting atoms, these again being further characterized by their immediate neighbor atoms. The calculation of their group contributions, carried out by means of a fast Gauss–Seidel fitting calculus, used the experimental data of 5988 molecules from literature. An immediate subsequent ten-fold cross-validation test confirmed the extraordinary accuracy of the prediction of the molar refractivity, indicated by a correlation coefficient R^2 and a cross-validated analog Q^2 of 0.9997, a standard deviation σ of 0.38, a cross-validated analog S of 0.41, and a mean absolute deviation of 0.76%. The high reliability of the predictions has been exemplified with three classes of molecules: ionic liquids, silicon- and boron-containing compounds. The corresponding molecular polarizabilities have been calculated indirectly from the refractivity using the inverse Lorentz-Lorenz relation. In addition, it could be shown that there is a close relationship between the "true" volume and the refractivity of a molecule, revealing an excellent correlation coefficient R^2 of 0.9645 and a mean absolute deviation of 7.53%.

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QSPR Models for the Molar Refraction, Polarizability and Refractive Index of Aliphatic Carboxylic Acids Using the ZEP Topological Index

Cited by 8 publications

References 20 publications

Understanding Refractive Index Changes in Homologous Series of Unbranched Organic Compounds Based on Beer's Law

Understanding Refractive Index Changes in Homologous Series of Unbranched Organic Compounds Based on Beer's Law

Symmetrical Bispyridinium Compounds Act as Open Channel Blockers of Cation-Selective Ion Channels

Revision and Extension of a Generally Applicable Group-Additivity Method for the Calculation of the Refractivity and Polarizability of Organic Molecules

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