Determination of solvation descriptors for terpene hydrocarbons from chromatographic measurements

•Prediction of chromatographic rentention data for terpene hydrocarbons.•Development of predictive linear free energy relationships.•Calculation of solute descriptors for terpene hydrocarbons. Gas chromatographic retention data on 107 terpene hydrocarbons from the literature together with other data...

Full description

Saved in:
Bibliographic Details
Published in:Journal of Chromatography A 2013-06, Vol.1293, p.133-141
Main Authors: Abraham, Michael H., Gola, Joelle R.M., Gil-Lostes, Javier, Acree, William E., Cometto-Muñiz, J. Enrique
Format: Article
Language:English
Subjects:
Accuracy
Aliphatic compounds
Analytical chemistry
Chemistry
Chromatographic methods and physical methods associated with chromatography
Chromatography
Descriptors
Exact sciences and technology
Fragmentation
Gas chromatographic methods
Gas liquid chromatography
Hydrocarbons
Linear free energy relationships
Mathematical analysis
Partition coefficient
partition coefficients
Partitions
Terpenes
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:•Prediction of chromatographic rentention data for terpene hydrocarbons.•Development of predictive linear free energy relationships.•Calculation of solute descriptors for terpene hydrocarbons. Gas chromatographic retention data on 107 terpene hydrocarbons from the literature together with other data have been used to obtain a set of Abraham descriptors for these 107 compounds. For 88 aliphatic cyclic terpene hydrocarbons, a fragmentation scheme was constructed that allows key descriptors to be estimated just from structure. The total set of descriptors, including those estimated by the fragmentation schemes, were then used to predict water–octanol partition coefficients for the 88 compounds, there being good agreement with values calculated from a number of well-known programs. For a small number of terpene hydrocarbons, there was good agreement between predicted and experimental values of nasal pungency thresholds, and predicted and experimental gas–blood, gas–oil, and gas–water partition coefficients. It is suggested that the descriptors obtained for the 107 terpene hydrocarbons can be used to predict water–solvent partition coefficients, gas–solvent partition coefficients, and partition coefficients in a number of biological systems.
ISSN:0021-9673
DOI:10.1016/j.chroma.2013.03.068