O-17 NMR-SPECTROSCOPY OF BENZOYL COMPOUNDS Y-C6H4-COX - SENSITIVITY TO RING SUBSTITUENTS AS A MEASURE OF THE ELECTRON DEMAND OF THE CARBONYL GROUP

被引：52

作者：

DAHN, H

PECHY, P

TOAN, VV

机构：

[1] Institut de Chimie Organique, Université de Lausanne, Lausanne, CH-1005

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 06期

关键词：

D O I：

10.1002/anie.199006471

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Contrary to the consensus of opinion 13C‐NMR spectroscopy is not suitable for the determination of electron density at the carbonyl C‐atom. However, by measurement of the 17O‐chemical shift in aromatic carbonyl compounds Y‐C6H4‐COX, X = CF3, H, CH3, CO2R, Br, Cl, F, OCOAryl, SR, OR, NH2, OH, O⊖, reliable statements could be made about the electrophilicity of the carbonyl C‐atom. It is gratifying that the results are in agreement with classical chemical rules. There is much to be said for 17O‐NMR spectroscopy being given more attention than hitherto. Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany

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页码：647 / 648

页数：2

相关论文

共 26 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] O-17 NMR-SPECTROSCOPY - EFFECT OF SUBSTITUENTS ON CHEMICAL-SHIFTS FOR PARA-SUBSTITUTED BENZOIC-ACIDS, METHYL BENZOATES, CINNAMIC-ACIDS AND METHYL CINNAMATES [J].

BALAKRISHNAN, P ;

BAUMSTARK, AL ;

BOYKIN, DW .

ORGANIC MAGNETIC RESONANCE, 1984, 22 (12) :753-756

[3] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[4] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .23. NEW SIGMA-+ CONSTANTS FOR ACTIVATING SUBSTITUENTS - SOLVOLYSIS OF 1-ARYL-1-CYCLOPROPYL 3,5-DINITROBENZOATES CONTAINING ACTIVATING SUBSTITUENTS IN ARYL GROUP - TOOL OF INCREASING ELECTRON DEMAND AND I-STRAIN [J].

BROWN, HC ;

RAO, CG ;

RAVINDRANATHAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (23) :7663-7667

[5] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .18. RELATIVE ELECTRON RELEASING PROPERTIES OF METHYL, PHENYL, AND CYCLOPROPYL GROUPS TO ELECTRON DEFICIENT CENTER AS INDICATED BY SOLVOLYSIS - CRITICAL-EXAMINATION OF C-13 CHEMICAL-SHIFTS AS A BASIS FOR ESTABLISHING ELECTRON-DENSITIES IN CARBONIUM-IONS [J].

BROWN, HC ;

PETERS, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1712-1716

[6]

BROWN PV, 1977, NONCLASSICAL ION PRO, P163

[7] CORRELATIONS BETWEEN IR FREQUENCIES AND SUBSTITUENT CONSTANTS .2. SUBSTITUTED BENZENES [J].

BROWNLEE, RTC ;

DISTEFANO, J ;

TOPSOM, RD .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1975, 31 (11) :1685-1693

[8] ABINITIO MO CALCULATIONS AND O-17 NMR AT NATURAL ABUNDANCE OF PARA-SUBSTITUTED ACETOPHENONES [J].

BROWNLEE, RTC ;

SADEK, M ;

CRAIK, DJ .

ORGANIC MAGNETIC RESONANCE, 1983, 21 (10) :616-620

[9] CORRELATION OF O-17 NMR AND O-17 NQR DATA FOR SOME AROMATIC CARBONYL-COMPOUNDS [J].

CHENG, CP ;

LIN, SC ;

SHAW, GS .

JOURNAL OF MAGNETIC RESONANCE, 1986, 69 (01) :58-67

[10] O-17 NUCLEAR-QUADRUPOLE DOUBLE-RESONANCE SPECTROSCOPY .1. INTRODUCTION - RESULTS FOR ORGANIC CARBONYL-COMPOUNDS [J].

CHENG, CP ;

BROWN, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (09) :2327-2334