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1999
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January
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In the Laboratory
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A Simple Method for Determining the Absolute Configuration of a-Amino Acids
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María Dolores Díaz-de-Villegas
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón,
Universidad de Zaragoza-CSIC, 50009 Zaragoz, Spain
Esteban P. Urriolabeitia
Departamento de Química Inorgánica, Instituto de Ciencia de Materiales de Aragón,
Universidad de Zaragoza-CSIC, 50009 Zaragoz, Spain
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January 1999
Vol. 76 No. 1
p. 77
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| Abstract |
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The reaction of [Pd(dmba)(acac)] (dmba = C6H4CH2NMe2-2 or 2-[(dimethylamino)methyl]phenyl-C1,N; acac = C5H7O2 or acetylacetonate) with optically pure a-amino acids (HAa, 1:1 molar ratio) [HAa = S-alanine, S-2-amino butyric acid, R-2-amino butyric acid, (2S,3S)-isoleucine, (2S,3R)-threonine and S-asparagine] in refluxing MeOH results in the formation of the corresponding neutral complexes [Pd(dmba)(Aa)] in good yield. The CD (circular dichroism) spectra of these complexes have been measured. The analysis of the shape of the CD curves reveals that all complexes with the same configuration at Ca display similar CD curves, whereas complexes with opposite configuration at Ca display CD curves that are mirror images. Thus, these complexes could be used as analytical tools in the assignment of absolute configurations of a-amino acids.
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| Supplement |
Figures for the laboratory are available as supplementary material. The figures are in a ChemDraw document, which can be accessed as either a zip file (for Windows) or a sit file (for Macintosh).
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Citation |
Diaz-de-Villegas, Maria Dolores; Urriolabeitia, Esteban P. J. Chem. Educ. 1999 76 77.
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Keywords |
Inorganic Chemistry; Organic Chemistry; Organometallics; Qualitative Analysis; Amino Acids; Laboratory Instruction
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History |
Created:
Last Updated: |
June 15, 1999
November 22, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1999
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January
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77
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