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
收藏
页码：1213 / 1221
页数：9
相关论文
共 41 条
  • [1] A DFT-based exploration augmented by X-ray and NMR of the stereoselectivity in the 1,3-dipolar cycloaddition of 1-pyrroline-1-oxide to methyl cinnamate and benzylidene acetophenone
    Acharjee, Nivedita
    Das, Tapas Kumar
    Banerji, Avijit
    Banerjee, Manas
    Prange, Theirry
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2010, 23 (12) : 1187 - 1195
  • [2] [Anonymous], 2004, GAUSSIAN 03 REVISION
  • [3] Banerji A, 2004, INDIAN J CHEM B, V43, P880
  • [4] 1,3-dipolar cycloadditions VI.: Structure and conformation of cycloadducts from reactions of C-aryl-N-phenylnitrones with substituted cinnamic acid amides
    Banerji, A
    Maiti, KK
    Haldar, S
    Mukhopadhyay, C
    Banerji, J
    Prangé, T
    Neuman, A
    [J]. MONATSHEFTE FUR CHEMIE, 2000, 131 (08): : 901 - 911
  • [5] 1,3-dipolar cycloadditions.: Part XII -: Selective cycloaddition route to 4-nitroisoxazolidine ring systems
    Banerji, Avijit
    Gupta, Maya
    Biswas, Pizush Kanti
    Prange, Thierry
    Neuman, Alain
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) : 1045 - 1049
  • [6] Conformational preferences of methacrolein in Diels-Alder and 1,3-dipolar cycloaddition reactions
    Barba, Carmen
    Carmona, Daniel
    Garcia, Jose Ignacio
    Lamata, Maria Pilar
    Mayoral, Jose Antonio
    Salvatella, Luis
    Viguri, Fernando
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) : 9831 - 9840
  • [7] Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model
    Barone, V
    Cossi, M
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) : 1995 - 2001
  • [8] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [9] Theoretical analysis of the regioselectivity of 1,3-dipolar cycloaddition of C-(methoxycarbonyl)-N-methyl with methyl acrylate and vinyl acetate
    Benchouk, W.
    Mekelleche, S. M.
    [J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2008, 852 (1-3): : 46 - 53
  • [10] Stereoselective 1,3-dipolar cycloadditions of a chiral nitrone derived from erythrulose.: An experimental and DFT theoretical study
    Carda, M
    Portolés, R
    Murga, J
    Uriel, S
    Marco, JA
    Domingo, LR
    Zaragozá, RJ
    Röper, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 7000 - 7009
12345