Enantioselective correlation between retention factor and lipophilicity index in chiral separation on cellulose and amylose tris(3,5-dimethylphenylcarbamate) CSPs in reversed mode: A case study

• Published in: Chirality (New York, N.Y.) Vol. 13; no. 1; pp. 56 - 61
• Main Authors: Roussel, Christian, Bonnet, Brice, Piederriere, Anne, Suteu, Cristina
• Format: Journal Article
• Language: English
• Published: New York John Wiley & Sons, Inc 2001
• Subjects: chiral HPLC; chiral recognition; hydrophobic interactions; substituent effect
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/1520-636X(2001)13:1<56::AID-CHIR11>3.0.CO;2-W

For a series of alkyl substituted N‐arylthiazoline‐2‐(thi)one atropisomers 1–14, lipophilicity indexes log kw obtained by polycratic RP‐HPLC were compared to ln k(+)‐S and ln k(−)‐R obtained on CHIRALCEL OD‐R® (reversed mode) and CHIRALPAK AD‐RH® (reversed mode). Linear correlations were obtained in most cases. It appears that the correlation lines for R and S enantiomers may be parallel, convergent, or divergent, accounting for the observed α variation in going from methyl to tert‐butyl series. Some tentative hypothesis are given as future investigation routes. Chirality 13:56–61, 2001. © 2000 Wiley‐Liss, Inc.