Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids

Autores
Padró, Juan Manuel; Pellegrino Vidal, Rocio; Reta, Mario Roberto
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.
Fil: Padró, Juan Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Pellegrino Vidal, Rocio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Reta, Mario Roberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Materia
Nitrogen-Based Ionic Liquids
Phosphonium-Based Ionic Liquids
Partition Coefficients
Liquid-Liquid Extraction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/32938
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/32938
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquidsPadró, Juan ManuelPellegrino Vidal, RocioReta, Mario RobertoNitrogen-Based Ionic LiquidsPhosphonium-Based Ionic LiquidsPartition CoefficientsLiquid-Liquid Extractionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.Fil: Padró, Juan Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaFil: Pellegrino Vidal, Rocio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaFil: Reta, Mario Roberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; ArgentinaSpringer Heidelberg2014-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/32938Pellegrino Vidal, Rocio; Reta, Mario Roberto; Padró, Juan Manuel; Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids; Springer Heidelberg; Analytical and Bioanalytical Chemistry; 406; 30; 10-2014; 8021-80311618-2642CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s00216-014-8264-zinfo:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00216-014-8264-zinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:47Zoai:ri.conicet.gov.ar:11336/32938instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:44:47.295CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
title Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
spellingShingle Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
Padró, Juan Manuel
Nitrogen-Based Ionic Liquids
Phosphonium-Based Ionic Liquids
Partition Coefficients
Liquid-Liquid Extraction
title_short Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
title_full Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
title_fullStr Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
title_full_unstemmed Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
title_sort Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids
dc.creator.none.fl_str_mv Padró, Juan Manuel
Pellegrino Vidal, Rocio
Reta, Mario Roberto
author Padró, Juan Manuel
author_facet Padró, Juan Manuel
Pellegrino Vidal, Rocio
Reta, Mario Roberto
author_role author
author2 Pellegrino Vidal, Rocio
Reta, Mario Roberto
author2_role author
author
dc.subject.none.fl_str_mv Nitrogen-Based Ionic Liquids
Phosphonium-Based Ionic Liquids
Partition Coefficients
Liquid-Liquid Extraction
topic Nitrogen-Based Ionic Liquids
Phosphonium-Based Ionic Liquids
Partition Coefficients
Liquid-Liquid Extraction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.
Fil: Padró, Juan Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Pellegrino Vidal, Rocio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
Fil: Reta, Mario Roberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina
description The partition coefficients, P IL/w, of several compounds, some of them of biological and pharmacological interest, between water and room-temperature ionic liquids based on the imidazolium, pyridinium, and phosphonium cations, namely 1-octyl-3-methylimidazolium hexafluorophosphate, N-octylpyridinium tetrafluorophosphate, trihexyl(tetradecyl)phosphonium chloride, trihexyl(tetradecyl)phosphonium bromide, trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide, and trihexyl(tetradecyl)phosphonium dicyanamide, were accurately measured. In this way, we extended our database of partition coefficients in room-temperature ionic liquids previously reported. We employed the solvation parameter model with different probe molecules (the training set) to elucidate the chemical interactions involved in the partition process and discussed the most relevant differences among the three types of ionic liquids. The multiparametric equations obtained with the aforementioned model were used to predict the partition coefficients for compounds (the test set) not present in the training set, most being of biological and pharmacological interest. An excellent agreement between calculated and experimental log P IL/w values was obtained. Thus, the obtained equations can be used to predict, a priori, the extraction efficiency for any compound using these ionic liquids as extraction solvents in liquid-liquid extractions.
publishDate 2014
dc.date.none.fl_str_mv 2014-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/32938
Pellegrino Vidal, Rocio; Reta, Mario Roberto; Padró, Juan Manuel; Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids; Springer Heidelberg; Analytical and Bioanalytical Chemistry; 406; 30; 10-2014; 8021-8031
1618-2642
CONICET Digital
CONICET
url http://hdl.handle.net/11336/32938
identifier_str_mv Pellegrino Vidal, Rocio; Reta, Mario Roberto; Padró, Juan Manuel; Partition coefficients of organic compounds between water and imidazolium-, pyridinium-, and phosphonium-based ionic liquids; Springer Heidelberg; Analytical and Bioanalytical Chemistry; 406; 30; 10-2014; 8021-8031
1618-2642
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s00216-014-8264-z
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs00216-014-8264-z
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Springer Heidelberg
publisher.none.fl_str_mv Springer Heidelberg
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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