A chiral recognition model for the chromatographic resolution of N-acylated 1-aryl-1-aminoalkanes

Abstract

for most generous support, and Professor I. O. Sutherland for spectra of nonactic acid derivatives. Registry No.

Synthesis and evaluation of a new biselector s‐triazine based chiral stationary phase for enantioselective HPLC: potentiality of the approach and perspectives

“…Not only these racemic analytes were well resolved on CSP2 (Fig. 3), but the extent of the enantioseparations was also similar to that observed on CSP4 for compounds belonging to the same class (Pirkle and Welch, 1983).…”

Chiral separation by chromatographic and electromigration techniques. A Review

“…An overview of the immense work done in this lab is given by Welch [45]. Pirkle proposed a chiral recognition model for the N-DNBPG phase based on p-p interactions, dipole stacking and hydrogen bondings [46]. Several specially designed CSPs were developed making use of the reciprocal nature of chiral recognition by immobilizing the target analyte and checking several compounds as potential chiral selectors [47].…”

Resolution of Racemic N-Acyl-1-arylaminoalkanes on a (3,5-Dinitrobenzoyl)phenylglycinol-Derived High Performance Liquid Chromatography Chiral Stationary Phase

“…As shown in Table 1, three compounds (1a, 1b, 1c) were separated well on CSP 2, the separation factors of the three compounds decreasing continuously as the acyl tail increased in length. From the chromatographic resolution behavior similar to that on a commercially available DNB-phenylglycine CSP (6,10), the continuous decrease in the ␣ value observed in the resolution of compounds 1a, 1b, and 1c on CSP 2 can be rationalized by assuming that the acyl tail intercalates between the strands of the connecting arm of the CSP.…”

“…Test racemic materials were prepared according to procedures described previously (10). Solvents for HPLC analysis were of Merck HPLC grade.…”