POLARIZED C-H GROUPS AS NOVEL HYDROGEN-BOND DONORS IN HYDRYL-F-ALKYL ESTERS - UNEQUIVOCAL EXAMPLES FOR THE PINCHAS-EFFECT

被引：24

作者：

ADCOCK, JL

ZHANG, HQ

机构：

[1] Department of Chemistry, University of Tennessee, Knoxville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 07期

关键词：

D O I：

10.1021/jo00112a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H-1 NMR and IR spectral evidence for a C-H...O hydrogen bonds in 1-[2-hydryl-F-adamantyl] trifluoroacetate and 1,3-[2-hydryl-F-adamantyl] bis(trifluoroacetate) are presented. Evidence indicating a three-center hydrogen bond in 1,3-[2-hydryl-F-adamantyl] bis-(trifluoroacetate) is also presented. Both compounds, despite otherwise normal H-1 NMR chemical shift displacements and carbonyl stretching frequency depressions, show strong increases in C-H stretching frequencies related to hydrogen-bond interactions (the ''Pinchas Effect'').

引用

页码：1999 / 2002

页数：4

共 23 条

[1] AEROSOL FLUORINATION OF 1-CHLOROADAMANTANE, 2-CHLOROADAMANTANE, AND METHYL 1-ADAMANTYLACETATE - A NOVEL SYNTHETIC APPROACH TO 1-SUBSTITUTED AND 2-SUBSTITUTED HYDRYL-F-ADAMANTANES, METHYL-F-ADAMANTANES, AND (DIFLUOROMETHYL)-F-ADAMANTANES [J].