Evaluation of the aggregation process in a mixture of propofol and benzocaine

We report on a mass-resolved IR spectrosopic study on propofol-benzocaine aggregates. This is a complex system due to the several conformational isomers that both monomers may adopt and to the combination of functional groups they present, which allow the molecules to interact in many possible ways....

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Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2019-02, Vol.21 (7), p.3537-3544
Main Authors: León, I, Lesarri, A, Fernández, J A
Format: Article
Language:English
Subjects:
Agglomeration
Benzocaine - chemistry
Complex systems
Dispersion
Functional groups
Isomers
Organic chemistry
Propofol - chemistry
Spectrophotometry, Infrared
Stoichiometry
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Summary:We report on a mass-resolved IR spectrosopic study on propofol-benzocaine aggregates. This is a complex system due to the several conformational isomers that both monomers may adopt and to the combination of functional groups they present, which allow the molecules to interact in many possible ways. However, our results demonstrate that a single conformation is favored for each stoichiometry. In the heterodimer, propofol acts as a proton donor to the ester group of benzocaine, while the whole cluster is stabilized by dispersive forces. These dispersive forces account for an important part of the system's stabilization energy as the calculations suggest. Propofol does not show any affinity for the amino group of benzocaine, even when a second molecule of propofol is introduced. These results demonstrate the difficulty in anticipating the aggregation preferences of even small organic molecules.
ISSN:1463-9076
1463-9084
DOI:10.1039/c8cp04386h