Experimental and Theoretical Study of the Products from the Spontaneous Dimerization of DL- and D-Glyceraldehyde


  • Federico García-Jiménez Universidad Nacional Autónoma de México
  • Ofelia Collera Zúñiga Universidad Nacional Autónoma de México
  • Yolanda Castells García Universidad Nacional Autónoma de México
  • Julio Cárdenas Universidad La Salle
  • Gabriel Cuevas Universidad Nacional Autónoma de México


DL-glyceraldehyde, D-glyceraldehyde, 1,4-dioxanes, nuclear magnetic resonance, density functional calculations, stereoelectronic effects, anomeric effect, hydrogen bond, weak interactions


Abstract. The predominant molecular structure of DL and D-glyceraldehyde has been studied with infrared and nuclear magnetic resonance spectroscopies. Both techniques show  that these compounds at room temperature have a minor percentage of the aldehydic form. These studies showed that D-(+)-glyceraldehyde coexists in a minor proportion as a component of a complex mixture of diasteroisomers of the 2,5-dihydroxy-3,6-dihydroxymethyl-1,4-dioxane, while the racemic mixture is made of two main compounds. The stability of the isolated diasteroisomers is controlled by the formation of intramolecular hydrogen bonds that are formed under the control of the anomeric effect which defines the favored position for the hydroxyl group. The endo and exo-anomeric interactions have their origin in the stereoelectronic interaction nO → σ*C-O. Using theoretical calculations at B3LYP/6-31G(d,p) level, it was possible to establish the structure of the favored conformers.


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Author Biographies

Federico García-Jiménez, Universidad Nacional Autónoma de México

Instituto de Química

Ofelia Collera Zúñiga, Universidad Nacional Autónoma de México

Instituto de Química

Yolanda Castells García, Universidad Nacional Autónoma de México

Escuela Nacional Preparatoria Plantel Antonio Caso

Julio Cárdenas, Universidad La Salle

Escuela de Ciencias Químicas

Gabriel Cuevas, Universidad Nacional Autónoma de México

Instituto de Química


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