Issue 12, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation†

Andreas M. Zissimos,*a   Michael H. Abraham,a   Chau M. Du,b   Klara Valko,c   Chris Bevan,c   Derek Reynolds,d   John Woode  and  Kin Y. Tamf  

* Corresponding authors

a Department of Chemistry, University College London, 20 Gordon Street, London, UK
E-mail: a.zissimos@ucl.ac.uk
Fax: +44-020-7679-7463

b pION Inc., 5 Constitution Way, Woburn, MA 01801, USA

c Hit Generation Sciences, Analytical Technologies Unit, GlaxoSmithKline Medicines Research Centre, Stevenage, Herts., UK

d REYTEK Ltd, 11C Rothsday Rd., Bedford, Bedfordshire, UK

e Statistical Sciences, GlaxoSmithKline, NFSP, Third Ave, Harlow, Essex, UK

f AstraZeneca Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire, UK

Abstract

Solvation equations have been obtained for seven high performance liquid chromatographic (HPLC) systems, generated in the reverse phase (RP) mode with fast gradient elution. A training set of 40 compounds was used for each system. The seven equations were then used to calculate Abraham descriptors for a completely separate 40-compound test set. In this way the three descriptors dipolarity/polarizability S, hydrogen bond acidity A, and hydrogen bond basicity B were obtained. Five different procedures were used to calculate the descriptors, (i) Microsoft ‘Solver’, (ii) a program that uses a set of three simultaneous equations, and which we denote as ‘TripleX’, (iii) a program similar to Solver that we denote as ‘Descfit’, (iv) a series of regression equations developed from compounds with known descriptors and (v) a series of modified regression equations. We show that RP-HPLC data for a given compound in seven systems can be used to calculate the three Abraham descriptors reliably. We compare descriptors, and errors in the method, with those obtained from water–solvent partition systems.

Graphical abstract: Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation

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Article information

DOI
https://doi.org/10.1039/B206927J
Article type
Paper
Submitted
17 Jul 2002
Accepted
08 Oct 2002
First published
04 Nov 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 2001-2010

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Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation

A. M. Zissimos, M. H. Abraham, C. M. Du, K. Valko, C. Bevan, D. Reynolds, J. Wood and K. Y. Tam, J. Chem. Soc., Perkin Trans. 2, 2002, 2001 DOI: 10.1039/B206927J

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