VIBRATIONAL SPECTRA OF 4-PYRIDONE AND ITS 2,3,5,6-TETRADEUTERO, N-DEUTERO, N-METHYL, N-CYANO, AND 3,5-DIHALOGENO DERIVATIVES . MIXING BETWEEN C=C AND C=O STRETCHING VIBRATIONS

被引:21
作者
BATTS, BD
SPINNER, E
机构
[1] Department of Medical Chemistry, John Curtin School of Medical Research, Australian National University, Canberra, ACT
关键词
D O I
10.1071/CH9692581
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The infrared spectra of the above compounds, and the Raman spectra of the parent compound and its 2,3,5,6-D4, 1-D, and 1-Me derivatives have been determined. The effects of electron-withdrawing infstituents, N-methylation, and deuteration on the two intense infrared bands in the 1480–1650 cm−1 region are not compatible with one being a C=O and the other a C=C stretching band. These two vibrations must be extensively mixed; occasionally very pronounced medium effects, which are not straightforward, are observed for one or both of these bands. The spectra are not in accord with a mostly zwitterionic (N-protonated pyrid-4-oxide) structure (II) of 4-pyridone. Band assignments are made for the parent compound. © 1969, CSIRO. All rights reserved.
引用
收藏
页码:2581 / &
相关论文
共 55 条
[1]   THE VIBRATION SPECTRA AND STRUCTURES OF THE HYDROXYPYRIDINES AND HYDROXYPYRIMIDINES IN AQUEOUS SOLUTION [J].
ALBERT, A ;
SPINNER, E .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1221-1226
[2]   IONIZATION CONSTANTS OF HETEROCYLIC SUBSTANCES .2. HYDROXY-DERIVATIVES OF NITROGENOUS SIX-MEMBERED RING-COMPOUNDS [J].
ALBERT, A ;
PHILLIPS, JN .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUN) :1294-1304
[3]   NOTE ON THE PREPARATION OF GAMMA-PYRIDONE [J].
BAK, B ;
CHRISTENSEN, D .
ACTA CHEMICA SCANDINAVICA, 1954, 8 (03) :390-392
[4]   VIBRATION-SPECTRAL AND STRUCTURAL COMPARISON OF 4-AMINOPYRIDINE CATION WITH 4-HYDROXYPYRIDINIUM ION AND 4-PYRIDONE . PROTIO PARENT IONS, N- AND C-DEUTERATED, AND N-METHYLATED IONS . RELEVANT NMR SPECTRAL STUDIES [J].
BATTS, BD ;
SPINNER, E .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (12) :2595-&
[5]  
BATTS BD, UNPUBLISHED DATA
[6]   PROTON TRANSFER IN HYDROGEN BONDED SYSTEMS [J].
BELLAMY, LJ ;
ROGASCH, PE .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1960, 257 (1288) :98-108
[7]   THE USE OF SOLVENT EFFECTS IN THE IDENTIFICATION OF CARBONYL ABSORPTIONS IN PYRIDONES [J].
BELLAMY, LJ ;
ROGASCH, PE .
SPECTROCHIMICA ACTA, 1960, 16 (1-2) :30-34
[8]  
Clarke K, 1960, J CHEM SOC, P1885
[9]   VIBRATIONAL SPECTRA OF PYRIDINIUM SALTS [J].
COOK, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (10) :2009-&
[10]   INFRARED SPECTRA OF COMPLEXES OF 4-PYRIDONES [J].
COOK, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1963, 41 (02) :515-&