On the structure of prilocaine in aqueous and amphiphilic solutions

The solvation of prilocaine has been investigated in pure water and in an amphiphilic methanol/water solution using a combination of neutron diffraction with isotopic substitution augmented by Empirical Potential Structure Refinement (EPSR) simulations. This combination of techniques allows for deta...

Full description

Saved in:
Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2017, Vol.19 (20), p.12665-12673
Main Authors: Silva-Santisteban, Alvaro, Steinke, Nicola, Johnston, Andrew J, Ruiz, Guadalupe N, Carlos Pardo, Luis, McLain, Sylvia E
Format: Article
Language:English
Subjects:
Amines
Atomic structure
Computer simulation
Dinàmica molecular
Física
Hydration
Hydrochlorides
Liquids
Líquids
Methyl alcohol
Molecular dynamics
Neutron diffraction
Simulació per ordinador
Simulation
Solvation
Àrees temàtiques de la UPC
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The solvation of prilocaine has been investigated in pure water and in an amphiphilic methanol/water solution using a combination of neutron diffraction with isotopic substitution augmented by Empirical Potential Structure Refinement (EPSR) simulations. This combination of techniques allows for details of the solvation structure on the atomic scale to be unravelled. The hydration of prilocaine is significantly altered relative to when this molecule is in pure water (as a hydrochloride salt) or in an amphiphilic environment (as a freebase compound). Interestingly, there is not a significant change in hydration around the amine group on prilocaine hydrochloride compared with prilocaine as a freebase. Despite this group being an ammonium group in water and an amine group in methanol/water solutions, the hydration of this motif remains largely intact. The changes in hydration between prilocaine as a free base and prilocaine·HCl instead appears to arise from a change in hydration around the aromatic ring and the amide group in the prilocaine molecule.
ISSN:1463-9076
1463-9084
DOI:10.1039/c7cp01723e