An analysis of substituent effects on 1H and 13C NMR parameters of substituted furans.: Linear free energy relationships and PM3 semiempirical calculations

被引:20
作者
Alvarez-Ibarra, C [1 ]
Quiroga-Feijoo, ML [1 ]
Toledano, E [1 ]
机构
[1] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1998年 / 03期
关键词
D O I
10.1039/a706779h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Forty five furans have been obtained in a synthetic project designed to evaluate monothiosubstituted furans as potential food flavourings. A full NMR (H-1 and C-13) Study and PM3 molecular orbital semiempirical calculations have been carried out. Substituent-induced chemical shifts (SCS) for six and nine substituents at the 2- and 3-positions have been calculated and a separation of inductive and resonance effects of these substituents has been proposed. Finally, a linear correlation between the net atomic charges localized at ring carbons and their C-13 NMR chemical shifts has been established.
引用
收藏
页码:679 / 689
页数:11
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