DFT study of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones evidenced by NMR and X-ray analysis

被引：20

作者：

Acharjee, Nivedita ^{[1
]}

Banerji, Avijit ^{[1
]}

Prange, Thierry ^{[2
]}

机构：

[1] Univ Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India

[2] Univ Paris 05, Lab Cristallog & RMN Biol, UMR 8015, CNRS, F-75006 Paris, France

来源：

MONATSHEFTE FUR CHEMIE | 2010年 / 141卷 / 11期

关键词：

Energy barrier; Electrophilicity index; NMR spectroscopy; X-ray structure determination; METHYL ACRYLATE; QUANTITATIVE CHARACTERIZATION; DIELS-ALDER; NITRONE; REACTIVITY; ENERGY; C-(METHOXYCARBONYL)-N-METHYL; ACID;

D O I：

10.1007/s00706-010-0393-2

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A DFT/B3LYP/6-31G* study was carried out to predict the regio- and stereoselectivities of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones in terms of FMO theory, DFT-based reactivity indices, and activation energy calculations. The structures of the resultant 2,3,4,5-tetrasubstituted isoxazolidines were determined by means of NMR spectroscopy and X-ray analysis.

引用

页码：1213 / 1221

页数：9

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