Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins

We have studied 1:1 inclusion complexes of two imidazole-based ionic liquids within β-cyclodextrin: 1-dodecyl-3-methylimidazolium and 1-butyl-3-methylimidazolium. By means of an adaptive biasing force scheme, we obtained the free energy profile along two different pathways, differing in the orientat...

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Autores principales: Semino, R., Rodríguez, J.
Formato: JOUR
Materias:
Free energy
Hydrophobicity
Ionic liquids
Molecular dynamics
Adaptive biasing forces
Beta-cyclodextrin
Encapsulation process
Essential features
Hydrophobic tails
Inclusion complex
Minimum-energy structures
Stable structures
Cyclodextrins
beta cyclodextrin
beta cyclodextrin derivative
ionic liquid
chemistry
conformation
molecular dynamics
thermodynamics
beta-Cyclodextrins
Ionic Liquids
Molecular Conformation
Molecular Dynamics Simulation
Thermodynamics
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_15206106_v119_n14_p4865_Semino
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_15206106_v119_n14_p4865_Semino2023-10-03T16:20:29Z Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins Semino, R. Rodríguez, J. Free energy Hydrophobicity Ionic liquids Molecular dynamics Adaptive biasing forces Beta-cyclodextrin Encapsulation process Essential features Hydrophobic tails Inclusion complex Minimum-energy structures Stable structures Cyclodextrins beta cyclodextrin beta cyclodextrin derivative ionic liquid chemistry conformation molecular dynamics thermodynamics beta-Cyclodextrins Ionic Liquids Molecular Conformation Molecular Dynamics Simulation Thermodynamics We have studied 1:1 inclusion complexes of two imidazole-based ionic liquids within β-cyclodextrin: 1-dodecyl-3-methylimidazolium and 1-butyl-3-methylimidazolium. By means of an adaptive biasing force scheme, we obtained the free energy profile along two different pathways, differing in the orientations of the head-to-tail vector with respect to the primary-secondary rim axis. Regarding 1-dodecyl-3-methylimidazolium, we found one minimum energy structure for each pathway, in which the hydrophobic tail remains embedded within the cyclodextrin, while the headgroup lies ∼11-12 Å from one of the rims; the structure where the polar head lies near the primary rim is the most stable. The analysis of the free energy of encapsulation of 1-butyl-3-methylimidazolium shows two minima for each insertion pathway, each of them associated with configurations where the imidazolium head lies close to one of the polar rims. As such, the most stable structure corresponds to one where the hydrophobic tail lies embedded within the cyclodextrin, while its head is localized near the secondary rim. The results are interpreted in terms of a simple model which captures the essential features that control the encapsulation process. A comparison with available experimental data is presented. (Figure Presented). © 2015 American Chemical Society. Fil:Semino, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_15206106_v119_n14_p4865_Semino
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Free energy
Hydrophobicity
Ionic liquids
Molecular dynamics
Adaptive biasing forces
Beta-cyclodextrin
Encapsulation process
Essential features
Hydrophobic tails
Inclusion complex
Minimum-energy structures
Stable structures
Cyclodextrins
beta cyclodextrin
beta cyclodextrin derivative
ionic liquid
chemistry
conformation
molecular dynamics
thermodynamics
beta-Cyclodextrins
Ionic Liquids
Molecular Conformation
Molecular Dynamics Simulation
Thermodynamics
spellingShingle Free energy
Hydrophobicity
Ionic liquids
Molecular dynamics
Adaptive biasing forces
Beta-cyclodextrin
Encapsulation process
Essential features
Hydrophobic tails
Inclusion complex
Minimum-energy structures
Stable structures
Cyclodextrins
beta cyclodextrin
beta cyclodextrin derivative
ionic liquid
chemistry
conformation
molecular dynamics
thermodynamics
beta-Cyclodextrins
Ionic Liquids
Molecular Conformation
Molecular Dynamics Simulation
Thermodynamics
Semino, R.
Rodríguez, J.
Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
topic_facet Free energy
Hydrophobicity
Ionic liquids
Molecular dynamics
Adaptive biasing forces
Beta-cyclodextrin
Encapsulation process
Essential features
Hydrophobic tails
Inclusion complex
Minimum-energy structures
Stable structures
Cyclodextrins
beta cyclodextrin
beta cyclodextrin derivative
ionic liquid
chemistry
conformation
molecular dynamics
thermodynamics
beta-Cyclodextrins
Ionic Liquids
Molecular Conformation
Molecular Dynamics Simulation
Thermodynamics
description We have studied 1:1 inclusion complexes of two imidazole-based ionic liquids within β-cyclodextrin: 1-dodecyl-3-methylimidazolium and 1-butyl-3-methylimidazolium. By means of an adaptive biasing force scheme, we obtained the free energy profile along two different pathways, differing in the orientations of the head-to-tail vector with respect to the primary-secondary rim axis. Regarding 1-dodecyl-3-methylimidazolium, we found one minimum energy structure for each pathway, in which the hydrophobic tail remains embedded within the cyclodextrin, while the headgroup lies ∼11-12 Å from one of the rims; the structure where the polar head lies near the primary rim is the most stable. The analysis of the free energy of encapsulation of 1-butyl-3-methylimidazolium shows two minima for each insertion pathway, each of them associated with configurations where the imidazolium head lies close to one of the polar rims. As such, the most stable structure corresponds to one where the hydrophobic tail lies embedded within the cyclodextrin, while its head is localized near the secondary rim. The results are interpreted in terms of a simple model which captures the essential features that control the encapsulation process. A comparison with available experimental data is presented. (Figure Presented). © 2015 American Chemical Society.
format JOUR
author Semino, R.
Rodríguez, J.
author_facet Semino, R.
Rodríguez, J.
author_sort Semino, R.
title Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
title_short Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
title_full Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
title_fullStr Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
title_full_unstemmed Molecular Dynamics Study of Ionic Liquids Complexation within β-Cyclodextrins
title_sort molecular dynamics study of ionic liquids complexation within β-cyclodextrins
url http://hdl.handle.net/20.500.12110/paper_15206106_v119_n14_p4865_Semino
work_keys_str_mv AT seminor moleculardynamicsstudyofionicliquidscomplexationwithinbcyclodextrins
AT rodriguezj moleculardynamicsstudyofionicliquidscomplexationwithinbcyclodextrins
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