O-17 NMR-STUDIES ON ALKYL-SUBSTITUTED 1-TETRALONES - EFFECT OF TORSION ANGLE CHANGE AND REPULSIVE VANDERWAALS INTERACTIONS

被引：17

作者：

BOYKIN, DW ^{[1
]}

DEWPRASHAD, B ^{[1
]}

EISENBRAUN, EJ ^{[1
]}

机构：

[1] OKLAHOMA STATE UNIV,DEPT CHEM,STILLWATER,OK 74078

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 02期

关键词：

D O I：

10.1021/jo00289a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Natural abundance 17O NMR spectroscopic data, in acetonitrile at 75 °C, were obtained for 24 substituted 1-tetralones. Substituent effect additivity was observed for the 17O NMR chemical shifts for these compounds. Substituents ortho to the carbonyl group produced large (~40 ppm) downfield shifts. The downfield shifts could be quantitatively predicted based upon a combination of molecular mechanics estimated torsion angle twist of the carbonyl group and repulsive van der Waals interactions. A general method of analysis of carbonyl 17O NMR chemical shifts in semiflexible systems is presented and applied to previously published chromanone results. © 1990, American Chemical Society. All rights reserved.

引用

页码：425 / 429

页数：5

共 19 条

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