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Toward a generalization of the Clough‐Lutz‐Jirgensons effect: Chiral organic acids with alkyl, hydroxyl, and halogen substituents
Author(s) -
NitschVelasquez Lucia,
Autschbach Jochen
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20863
Subject(s) - chemistry , chirality (physics) , halogen , optical rotation , alkyl , amino acid , specific rotation , absolute configuration , sign (mathematics) , stereochemistry , molecule , computational chemistry , rotation (mathematics) , organic chemistry , chiral symmetry , mathematical analysis , biochemistry , physics , mathematics , geometry , quantum mechanics , quark , nambu–jona lasinio model
Abstract The optical rotation of natural amino acids becomes more positive when the medium is changed from approximately neutral to strongly acidic (Clough–Lutz–Jirgensons (CLJ) effect). In this work, it is shown by time–dependent density functional computations that the effect can be generalized to other α–substituted chiral carboxylic acids. The physical origin of the generalized CLJ effect is similar to that in amino acids, linking the absolute configuration directly to the sign of CLJ. For conformationally flexible molecules with small magnitudes of the optical rotation, the presence of a CLJ effect might aid the assignment of absolute configurations based on comparing experimental data with computed chiroptical responses. Chirality, 2010. © 2010 Wiley‐Liss, Inc.