Document type
Journal articles
Document subtype
Full paper
Title
Hydrogen Bonding. 47. Characterization of the Ethylene-Glicol-Heptane Partition System; Hydrogen Bond Acidity and Basicity of Peptides.
Participants in the publication
M. H. Abraham (Author)
F. Martins (Author)
Dep. Química e Bioquímica
R. C. Mitchell (Author)
C. J. Salter. (Author)
Summary
Twelve measured ethylene glycol–heptane partition coefficients, Peh, have been combined with 20 measured literature values and 44 indirectly determined values to give a set of 76 values. Excluding one value for benzamide, the log Peh values are correlated through our general solvation equation, log Peh = 0.336 − 0.075R2 − 1.201 π2H − 3.786 Σα2H − 2.201 Σβ2H + 2.085Vx with r2 = 0.966, sd = 0.28, and F = 386. The solute descriptor R2 is the excess molar refraction, π2H is the dipolarity/polarizability, Σα2H and Σβ2H are the overall hydrogen bond acidity and basicity, and Vx is the McGowan volume. The log Peh equation has then been used to obtain descriptors for eleven peptides, all of which are end?protected. It is shown that for these end?protected peptides, hydrogen bond basicity makes a greater contribution to log Peh than does hydrogen bond acidity.
Date of Submisson/Request
1998-06-09
Date of Acceptance
1998-10-19
Date of Publication
1999-02
Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA
Where published
JOURNAL OF PHARMACEUTICAL SCIENCES
Publication Identifiers
ISSN - 0022-3549
Publisher
John Wiley and Sons
Number of pages
7
Starting page
241
Last page
247
Document Identifiers
DOI -
https://doi.org/10.1021/js980242l
URL -
https://doi.org/10.1021/js980242l
Rankings
SCIMAGO Q1 (1999) - 1.154 - Pharmaceutical Sciences
Web Of Science Q1 (1999) - 2.270 - Chemistry, Medicinal
Web Of Science Q1 (1999) - 2.270 - Pharmacology & Pharmacy
Web Of Science Q1 (1999) - 2.270 - Chemistry