Use of 1H NMR chemical shifts to determine the absolute configuration and enantiomeric purity for enantiomers of 3,3′-disubstituted-MeO-BIPHEP derivatives

Gorobets, Evgueni; Parvez, Masood; Wheatley, Bronwen M. M.; Keay, Brian A.
February 2006
Canadian Journal of Chemistry;Feb2006, Vol. 84 Issue 2, p93
Academic Journal
The absolute configuration of a series of 3,3′-disubstituted-MeO-BIPHEP derivatives can be determined by the 1H NMR chemical shift of the methoxyl group when the 3,3′-disubsituted-MeO-BIPHEP derivative is mixed with (–)-(2R,3R)-dibenzoyltartaric acid ((–)-DBTA) (1:2) and its NMR spectrum is run in CDCl3. The chemical shift of the methoxyl group in the Sax enantiomer always occurred at higher field than the corresponding Rax enantiomer. Integration of the corresponding methoxyl signals provides the enantiomeric purity of any mixtures.


Related Articles

  • Enantiodiscrimination by NMR Spectroscopy. Uccello-Barretta, Gloria; Balzano, Federica; Salvadori, Piero // Current Pharmaceutical Design;Nov2006, Vol. 12 Issue 31, p4023 

    The analysis of enantiorecognition processes involves the detection of enantiomeric species as well as the study of chiral discrimination mechanisms. In both fields Nuclear Magnetic Resonance (NMR) spectroscopy plays a fundamental role, providing several tools, based on the use of suitable...

  • Simple One-electron Invariants of Molecular Chirality. A. Luzanov; Dmitry Nerukh // Journal of Mathematical Chemistry;May2007, Vol. 41 Issue 4, p417 

    Pseudoscalar measures of electronic chirality for molecular systems are derived using the spectral moment theory applied to the frequency-dependent rotational susceptibility. In this scheme a one-electron chirality operator $$\hat{\kappa}$$ naturally emerges as a quantum counterpart of the...

  • Enantioselective magnetochiral photochemistry. Rikken, G. L. J. A.; Raupach, E. // Nature;6/22/2000, Vol. 405 Issue 6789, p932 

    Reports on development in enantioselective magnetochiral photochemistry. Importance of chirality, in which chemical and physical systems are the mirror images of each other, in biochemistry; Reactions involving chiral molecules often require the participation of on specific enantiomer, or...

  • New chiral dihydroxycyclopropane block from L-tartaric acid. Khalikova, G.; Gimalova, F.; Egorov, V.; Miftakhov, M. // Russian Journal of Organic Chemistry;Sep2011, Vol. 47 Issue 9, p1439 

    The article focuses on the chiral dihydroxycyclopropane deritive I synthesis with an application of accessible L-tartaric acid as the chirality source. It says that L-tartaric acid dimethyl ester acetonide II was reduced with sodium tetrahydridobate and compound III was converted to...

  • Enhancement effects of (R) and (S) enantiomers and the racemate of a model enhancer on permeation of theophylline through human skin. V�vrov�, Katerina; Hrab�lek, Alexandr; Dole�al, Pavel // Archives of Dermatological Research;Aug2002, Vol. 294 Issue 8, p383 

    The conformation of a permeation enhancer, given their mechanism of action, could influence its enhancing properties, since the stratum corneum components form essentially a chiral environment. The racemate and both enantiomers of 6-aminohexanoic acid 2-octylester as model enhancers with one...

  • Enantiomer of micranthoside. Sagareishvili, T.; Tsitsishvili, V. // Chemistry of Natural Compounds;Jul2006, Vol. 42 Issue 4, p419 

    A dihydroflavonol glycoside called neomicranthoside was isolated from Eupatorium micranthum introduced into Georgia. It was established using chemical and spectral data that it was an enantiomer of micranthoside, the structure of which has been previously established. Both glycosides are...

  • Conformational analysis of the bicyclo - [4.4.1]undecan-11-one ring system. Parvez, Masood; Sorensen, Ted S; Sun, Fang // Canadian Journal of Chemistry;Mar2002, Vol. 80 Issue 3, p245 

    The first conformational analysis of a bicyclo[4.4.1]undecan-11-one system (1) is presented. Based on low-temperature [sup 13] C NMR line-broadening measurements and an X-ray structure of the 1,6-dibromo derivative (2), this ketone adopts a chiral conformation with approximate C[sub 2] symmetry...

  • Measuring chirality in NMR in the presence of a time-dependent electric field. Walls, Jamie D.; Harris, Robert A. // Journal of Chemical Physics;6/21/2014, Vol. 140 Issue 23, p234201-1 

    Traditional nuclear magnetic resonance (NMR) experiments are "blind" to chirality since the spectra for left and right handed enantiomers are identical in an achiral medium. However, theoretical arguments have suggested that the effective Hamiltonian for spin-1/2 nuclei in the presence of...

  • O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid as supramolecular resolving agent. Simon, H.; Marthi, K.; Pokol, Gy.; Fogassy, E.; Kozma, D. // Journal of Thermal Analysis & Calorimetry;2003, Vol. 74 Issue 1, p155 

    O,O'-di-p-toluoyl-(2R,3R)-tartaric acid (DPTTA) was investigated as supramolecular complex (SMC) forming resolving agent with three racemic alcohols (menthol, 4-methyl-2-pentanol, trans-2-iodo-cyclohexanol) by preparative scale experiments and thermoanalytical measurements. Despite the very...


Read the Article


Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics