Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study

被引：7

作者：

Fernandez-Herrera, Maria A. ^{[1
]}

Zavala-Oseguera, Claudia ^{[2
]}

Luis Cabellos, Jose ^{[2
]}

Sandoval-Ramirez, Jesus ^{[1
]}

Domingo, Luis R. ^{[3
]}

Merino, Gabriel ^{[2
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Fac Ciencias Quim, Puebla 72570, Pue, Mexico

[2] Ctr Invest & Estudios Avanzados, Dept Fis Aplicada, Unidad Merida, Merida 97310, Yuc, Mexico

[3] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

来源：

JOURNAL OF MOLECULAR MODELING | 2014年 / 20卷 / 04期

关键词：

DFT study; Polar Diels-Alder reaction; Steroidal diene; TADs; STEPWISE MECHANISMS; OXIDATION; 4-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE; EFFICIENT;

D O I：

10.1007/s00894-014-2207-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The participation of 4-substituted-1,2,4-triazoline-3,5-diones (TADs) in Diels-Alder reactions toward a series of dienes is studied at the M05-2X/6-31+G(d,p) level. These reactions show very low activation energies and complete endo selectivity, in agreement with the experimental data. For a dienic steroid model, the reaction presents an a-facial selectivity. Analysis of reactivity indices explains the superelectrophilic character of TADs, and low activation energy. The substituent and solvent effects are also evaluated.

引用

页数：7

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