In silico prediction of linear free energy relationship descriptors of neutral and ionic compounds

to connected objects

Abstract: We present a prediction model for linear free energy relationship (LFER) descriptors - excess molar refraction (E), dipolarity/polarizability (S), hydrogen bonding acidity (A) & basicity (B), McGowan volume (V), and interaction of cations (J(+)) and anions (J(-)) - of both ionic and neutral compounds at the same scale. From computational calculations using density functional theory, a conductor screening model, and the OBPROP program in Turbomole, we obtained the following physicochemical sub-parameters for 992 molecules and atoms, polar surface area, molecular weight, volume, energy of van der Waals, sigma moments, molar refraction, and hydrogen-bond donor and acceptor abilities of a molecule or an atom. By making selective combinations of these sub-parameters - including also the number of rings, OH groups, and hydrogen atoms attached to nitrogen - we obtained prediction models for the LFER descriptors V, E, S, A, and B with reasonable accuracies, i.e. for a training set of compounds all R-2 above 0.934. We validated the models by comparing calculated and experimentally determined LFER descriptors of a test set. Using the complete dataset, the following R-2 and SE values were obtained: E (R-2 = 0.949, SE = 0.136), S (R-2 = 0.940, SE = 0.378), A (R-2 = 0.936, SE = 0.148), B (R-2 = 0.973, SE = 0.160), J(+) (R-2 = 0.816, SE = 0.351), and J(-) (R-2 = 0.700, SE = 0.291). Furthermore, we demonstrated the applicability of the calculated LFER descriptors by predicting transfers of neutral and ionic compounds from water to propylene carbonate, sulfolane, and ethylene glycol with good accuracy. These results show that physicochemical properties of ionic and neutral compounds can be reliably predicted with identical LFER descriptors even for chemical entities that do not yet exist

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch
Notes
RSC Advances. 5 (2015), 80634-80642, DOI 10.1039/c5ra13595h, issn: 2046-2069
IN COPYRIGHT http://rightsstatements.org/page/InC/1.0 rs

Classification
Chemie
Keyword
Molekül
Anion
Hansch-Analyse

Event
Veröffentlichung
(where)
Freiburg
(who)
Universität
(when)
2015
Creator
Contributor

DOI
10.1039/c5ra13595h
URN
urn:nbn:de:bsz:25-freidok-133762
Rights
Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
25.03.2025, 1:42 PM CET

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Show original at data provider

Associated

Time of origin

  • 2015

Other Objects (12)

Beiträge zur Chemie des Aluminiums : Synthese, Struktur und Reaktivität monomerer Aminoalane, Additionsverbindungen der Aluminiumhalogenide

Hochschulschrift

Beiträge zur Chemie des Aluminiums : Synthese, Struktur und Reaktivität monomerer Aminoalane, Additionsverbindungen der Aluminiumhalogenide

Chemie mit schwach koordinierenden Anionen : Synthese einer neuen Klasse schwach koordinierender Anionen des Typs Al(ORF)-4, Lewis-Säure-Base-Addukte der sehr schwachen Lewis-Basen S8, P4 und P4S3 mit dem Ag+-Kation von Ag[Al(ORF)4], von homopolyatomaren Phosphorkationen zu Al(ORF)-4-Salzen neuer binärer Phosphor-Halogen-Kationen mit Polyphosphorskelett

Hochschulschrift

Chemie mit schwach koordinierenden Anionen : Synthese einer neuen Klasse schwach koordinierender Anionen des Typs Al(ORF)-4, Lewis-Säure-Base-Addukte der sehr schwachen Lewis-Basen S8, P4 und P4S3 mit dem Ag+-Kation von Ag[Al(ORF)4], von homopolyatomaren Phosphorkationen zu Al(ORF)-4-Salzen neuer binärer Phosphor-Halogen-Kationen mit Polyphosphorskelett

Thermodynamic properties of ionic liquids

Hochschulschrift

Thermodynamic properties of ionic liquids

Boron ionic liquids as potential hydrogen storage materials : = Bor-ionische Flüssigkeiten als potentielle Wasserstoffspeicher-Materialien

Hochschulschrift

Boron ionic liquids as potential hydrogen storage materials : = Bor-ionische Flüssigkeiten als potentielle Wasserstoffspeicher-Materialien

Chemistry in ionic liquids and prediction of their transport properties : = Chemie in ionischen Flüssigkeiten und die Vorhersage ihrer Transporteigenschaften

Hochschulschrift

Chemistry in ionic liquids and prediction of their transport properties : = Chemie in ionischen Flüssigkeiten und die Vorhersage ihrer Transporteigenschaften

Investigations on dynamic properties of ionic liquids towards their application as electrolytes : = Untersuchungen der dynamischen Eigenschaften Ionischer Flüssigkeiten im Hinblick auf ihre Anwendung als Elektrolyte

Hochschulschrift

Investigations on dynamic properties of ionic liquids towards their application as electrolytes : = Untersuchungen der dynamischen Eigenschaften Ionischer Flüssigkeiten im Hinblick auf ihre Anwendung als Elektrolyte

The contribution of molecular interaction potentials to properties and activities of ionic liquid ions in solution

Hochschulschrift

The contribution of molecular interaction potentials to properties and activities of ionic liquid ions in solution

Investigations of BF3 based compounds as additives, electrolytes and as coating agent for nickel-rich cathode material

Investigations of BF3 based compounds as additives, electrolytes and as coating agent for nickel-rich cathode material

Direct subvalent, polycationic group 13 cluster compounds: lessons learned on isoelectronic DMPE substituted gallium and indium tetracation salts

Direct subvalent, polycationic group 13 cluster compounds: lessons learned on isoelectronic DMPE substituted gallium and indium tetracation salts

Novel conducting salts for rechargeable lithium-ion batteries based on the difluorophosphato ligand : = Neuartige Leitsalze für Lithium-Ionen Akkumulatoren basierend auf dem Difluorphosphat-Liganden

Hochschulschrift

Novel conducting salts for rechargeable lithium-ion batteries based on the difluorophosphato ligand : = Neuartige Leitsalze für Lithium-Ionen Akkumulatoren basierend auf dem Difluorphosphat-Liganden

Li[B(OCH(CF3)2)4] - Synthesis optimization and characterization of its Electrolytes : = Li[B(OCH(CF3)2)4] - Syntheseoptimierung und Charakterisierung dessen Elektrolyte

Hochschulschrift

Li[B(OCH(CF3)2)4] - Synthesis optimization and characterization of its Electrolytes : = Li[B(OCH(CF3)2)4] - Syntheseoptimierung und Charakterisierung dessen Elektrolyte

Silver-Selenium complexes and phosphorus cations stabilised by weakly coordinating anions : = Silber-Selen Komplexe und Phosphorkationen stabilisiert durch schwach koordinierende Anionen

Hochschulschrift

Silver-Selenium complexes and phosphorus cations stabilised by weakly coordinating anions : = Silber-Selen Komplexe und Phosphorkationen stabilisiert durch schwach koordinierende Anionen

Related objects