Experimental and theoretical study of the products from the spontaneous dimerization of DL- and D-glyceraldehyde

Journal of the Brazilian Chemical Society

Federico García-jiménez²  Ofelia Collera Zúñiga²  Yolanda Castells García¹  Julio Cárdenas¹  Gabriel Cuevas² 

[1] ,Universidad Nacional Autónoma de México Instituto de Química México D.F. ,México

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

DOI  :  10.1590/S0103-50532005000300022

来源: SciELO

【 摘 要 】

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 ® s*C-O. Using theoretical calculations at B3LYP/6-31G(d,p) level, it was possible to establish the structure of the favored conformers.

【 授权许可】

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