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By Gideon Polya

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In a comprehensive study on the impact of the C8 /C9 stereochemistry on chiral recognition, the effect of inversion of a single configuration was also elucidated [33]. 3). Consistently, a dramatically lower degree of enantiorecognition was observed for the two epimeric CSPs (tBuCEQN and tBuCEQD CSPs), which makes these CSPs more or less useless for the tested analytes. The relative spatial orientation of the interaction sites, as influenced by the relative C8 /C9 stereochemistry, prohibits the favorable cooperative multisite binding mechanism in the epimeric CSPs and leads to the loss of stereodifferentiation and chromatographic enantioselectivity.

H-values are given in kJ mol−1 of added ligand. (Reproduced from J. , J. Phys. Chem. B, 105: 1670 (2001). 0 × 104 (R)-Leu 1 × 104 1 × 104 2 × 104 a For comparison, the corresponding K values for the nonchiral selectand DNB-Gly obtained by ITC are b included. A relative error, ∆Kb /Kb , estimated on the basis of the chi-square fitting in which an error of 5% of the measured quantity was assigned for each titration point is about ±30% (ITC) and ±50% (CD, UV). Source: Reproduced from J. M. Maier, W.

02% H2 O 3CPP 8% EA in n-hexane 3CPP 11% EA in n-hexane % ∆∆S (rel. 19 71 67 NH4Ac, ammonium acetate; Npg, α-neopentyl-glycine; DNZ, 3,5-dinitrobenzyloxycarbonyl; Z, benzyloxycarbonyl; Bz, benzoyl; Ac, acetyl; TFAE, 2,2,2-trifluoro-1-(9-anthryl)-ethanol; 1PP, 1-phenyl-propanol; 2PP, 2-phenylpropanol; 3CPP, 3-chloro-1-phenylpropanol; ACN, acetonitrile; EA, ethyl acetate. a T = 295 K. b T = 298 K. Data summarized from References 89, 50, 53. differences for the distereomeric adsorption complexes [52].

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