Vibrational assignment of 4-amino-3-penten-2-one

被引：23

作者：

Tayyari, SF ^{[1
]}

Raissi, H ^{[1
]}

Tayyari, F ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Dept Chem, Mashhad 91775, Iran

来源：

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2002年 / 58卷 / 08期

关键词：

intramolecular hydrogen bond; aminoketone; 4-amino-3-penten-2-one; vibrational spectra; alpha; beta-unsaturated-beta-ketoenamines;

D O I：

10.1016/S1386-1425(01)00620-5

中图分类号：

O433 [光谱学];

学科分类号：

0703 ; 070302 ;

摘要：

The infrared and Raman spectra of 4-amino-3-penten-2-one and its two deuterated analogous have been measured. Comparison between the spectra recorded with two techniques, density functional theory (DFT) calculations and the spectral behavior upon deuteration was used for assignment of the vibrational spectra of the titled compound. DFT suggests a relatively strong intramolecular bent hydrogen bond with (NO)-O-... distance in the range of 2.64-2.67 Angstrom, which is in agreement with the observed nuNH at 3180 cm(-1). Existence of an intermolecular hydrogen bond is also shown in both solid and solution phases. The spectroscopic data support the enamine structure for this compound rather than imine structure. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：1681 / 1695

页数：15

共 50 条

[1] INFRARED SPECTRA OF 4-AMINO-3-PENTEN-2-ONE 4-AMINO-3-METHYL-3-PENTEN-2-ONE AND THEIR DEUTERATED DERIVATIVES
DABROWSKI, J
TERPINSK.J
ROCZNIKI CHEMII, 1969, 43 (03): : 555 - +
[2] Vibrational assignment and structure of 4-amino-3-cyano-3-penten-2-one
Raissi, H
Tayyari, SF
Tayyari, F
JOURNAL OF MOLECULAR STRUCTURE, 2002, 613 (1-3) : 195 - 208
[3] Molecular conformation and intramolecular hydrogen bonding in 4-amino-3-penten-2-one
Tayyari, SF
Fazli, M
Milani-Nejad, F
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2001, 541 : 11 - 15
[4] N-SUBSTITUENT EFFECT OF 4-AMINO-3-PENTEN-2-ONE IN THE REACTION WITH PHENYLHYDRAZINE
KASHIMA, C
SHIRAI, S
YAMAMOTO, Y
HETEROCYCLES, 1979, 12 (05) : 657 - 660
[5] REACTIONS OF 4-AMINO-3-PENTEN-2-ONE AND ITS N-SUBSTITUTED DERIVATIVES WITH DIAZONIUM IONS
MACHACEK, V
CEGAN, A
HALAMA, A
ROZNAVSKA, O
STERBA, V
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1995, 60 (08) : 1367 - 1379
[6] Two photoisomerization mechanisms of 4-amino-3-penten-2-one: Hydrogen-atom migration and internal rotation
Yaehata, Hiroshi
Nagaya, Maki
Kudoh, Satoshi
Nakata, Munetaka
CHEMICAL PHYSICS LETTERS, 2006, 424 (4-6) : 279 - 284
[7] Effect of substitution on the intramolecular hydrogen bonding of 4-amino-3-penten-2-one:: Ab initio, AIM and NBO studies
Raissi, Heidar
Bakavol, Mehdi
Jimenez-Fabian, Isaac
Tajabadi, Javad
Mdoshfeghi, Effat
Jalbout, Abraham F.
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 847 (1-3): : 47 - 51
[8] Vibrational assignment, structure and intramolecular hydrogen bond of 4-methylamino-3-penten-2-one
Raissi, H
Moshfeghi, E
Farzad, F
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 62 (4-5) : 1004 - 1015
[9] Electronic structures, intramolecular hydrogen bond interaction, and aromaticity of substituted 4-amino-3-penten-2-one in ground and electronic excited state
Shahabi, Mahnaz
Raissi, Heidar
Mollania, Fariba
STRUCTURAL CHEMISTRY, 2015, 26 (02) : 491 - 506
[10] Electronic structures, intramolecular hydrogen bond interaction, and aromaticity of substituted 4-amino-3-penten-2-one in ground and electronic excited state
Mahnaz Shahabi
Heidar Raissi
Fariba Mollania
Structural Chemistry, 2015, 26 : 491 - 506

← 1 2 3 4 5 →