Intramolecular electronic and hydrogen-bonding interactions in N,N'-dimethyl-2,3-di-O-methyl-L-tartaramide

被引:12
作者
Aleman, C [1 ]
Galembeck, SE [1 ]
机构
[1] UNIV SAO PAULO, FAC FILOSOFIA CIENCIAS & LETRAS RIBEIRAO PRET, DEPT QUIM, BR-14049901 RIBEIRAO PRETO, SP, BRAZIL
关键词
D O I
10.1021/jo962081g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The changes in energy of the N,N'-dimethyl-2,3-di-O-methyl-L-tartaramide, model compound of polytartaramides based on 2,3-di-O-methyl-L-tartaric acid and 1,n-alkanediamine, have been analyzed by ab initio quantum mechanical calculations. The influences of the gauche oxygen effect have been investigated in the gas phase as well as in aqueous, chloroform, and carbon tetrachloride solutions. The results indicate that polarizable environments enhance the gauche oxygen effect, but the amount of stabilization depends on the electronic characteristics of the solvent.
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页码:6562 / 6567
页数:6
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