Vibrational and electronic circular dichroism studies on the axially chiral pyridine-N-oxide: trans-2,6-di-ortho-tolyl-3,4,5-trimethylpyridine-N-oxide

被引：3

作者：

Teodorescu, Florina ^{[1
]}

Nica, Simona ^{[1
]}

Uncuta, Cornelia ^{[1
]}

Bartha, Emeric ^{[1
]}

Filip, Petru Ivan ^{[1
]}

Vanthuyne, Nicolas ^{[2
]}

Roussel, Christian ^{[2
]}

Mandi, Attila ^{[3
]}

Toth, Laszlo ^{[3
]}

Kurtan, Tibor ^{[3
]}

Naubron, Jean-Valere ^{[4
]}

Man, Isabela-Costinela ^{[1
]}

机构：

[1] Romanian Acad, Inst Organ Chem CD Nenitzescu, Bucharest 060023, Romania

[2] Aix Marseille Univ, UMR Chirosci ISM2, Marseille, France

[3] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary

[4] Aix Marseille Univ, Spectropole, FR1739, Marseille, France

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 18-19期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC ALLYLATION; ENANTIOSELECTIVE ALLYLATION; BIPYRIDINE N; N'-DIOXIDES; AROMATIC-ALDEHYDES; ORGANOCATALYSTS; CATALYSTS; LIGANDS; ALLYLTRICHLOROSILANE; N; N-DIOXIDE; RESOLUTION;

D O I：

10.1016/j.tetasy.2015.08.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The absolute configuration of the resolved axially chiral pyridine-N-oxide derivative, (+/-)-trans-2,6-di-ortho-tolyl-3,4,5-trimethylpyridine-N-oxide, has been determined by VCD and ECD analyses supported by TD-DFT calculations carried out at different levels of theory. DFT calculations confirmed that in spite of the two biaryl axes, the compound is conformationally less flexible and the major conformer is stabilized by two weak hydrogen bonds formed between the hydrogen of the methyl group of the tolyl moieties and the nitroxide oxygen. The experimental VCD spectra of this compound and the previously studied (+/-)-2,6-di-sec-butyl-4-methylpyridine-N-oxide with two stereogenic centers were compared in the frequency range 1200-1300 cm(-1). A (+,-,+)/(-,+,-) pattern of bands was observed in both cases. By replacing the sec-butyl moieties with tolyl ones, the VCD peaks shifted toward higher frequencies and the intensities were increased. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1043 / 1049

页数：7

共 2 条

[1] URANYL CHLORIDE COMPLEXES OF PYRIDINE-N-OXIDE AND 4-SUBSTITUTED PYRIDINE-N-OXIDES - INFRA-RED SPECTRA ELECTRONIC SPECTRA AND MAGNETIC SUSCEPTIBILITY STUDIES
BALAKRIS.PV
PATIL, SK
VENKATAS.HV
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1966, 28 (02): : 537 - &
[2] Vibrational circular dichroism of 2,6-di-sec-butyl-4-methylpyridine and 2,6-di-sec-butyl-4-methylpyridine-N-oxide: theoretical evidence on the existence of multiple -CH, -CH2, and -CH3 ... O intramolecular hydrogen bonds on the nitroxide oxygen
Teodorescu, Florina
Naubron, Jean-Valere
Uncuta, Cornelia
Filip, Petru Ivan
Bartha, Emeric
Toader, Ana Maria
Man, Isabela Costinela
TETRAHEDRON-ASYMMETRY, 2014, 25 (09) : 725 - 735

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