C-13 NMR SPECTROSCOPIC AND AM1 STUDY OF THE INTRAMOLECULAR PROTON-TRANSFER IN ANILS OF SALICYLALDEHYDE AND 2-HYDROXYNAPHTHALENE-1-CARBALDEHYDE

被引：63

作者：

ALARCON, SH

OLIVIERI, AC

GONZALEZSIERRA, M

机构：

[1] FAC CIENCIAS BIOQUIM & FARMACEUT,DEPT QUIM ANALIT,RA-2000 ROSARIO,ARGENTINA

[2] FAC CIENCIAS BIOQUIM & FARMACEUT,IQUIOS,RA-2000 ROSARIO,ARGENTINA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 05期

关键词：

D O I：

10.1039/p29940001067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tautomeric equilibria in intramolecularly hydrogen bonded Schiff bases is studied on the basis of solution C-13 NMR chemical shifts. Variable temperature NMR spectroscopic data and comparison with appropriate models show that while anils of salicaldehyde exist as phenolic tautomers, those of 2-hydroxynaphthalene-1-carbaldehyde exist as equilibrium mixtures containing appreciable amounts of both enol and keto tautomers, the latter being slightly predominant. AM1 results concerning the relative stability of tautomers are in good agreement with the NMR spectroscopic information.

引用

页码：1067 / 1070

页数：4

共 28 条

[1] C-13 CPMAS NMR-STUDY OF SOLID ARYLAZONAPHTHOLS - EVIDENCE OF C-13, N-14 SELF-DECOUPLING INDUCED BY A SOLID-STATE PROTON-TRANSFER REACTION [J].