A molecular electron density theory study of the enhanced reactivity of aza aromatic compounds participating in Diels

A molecular electron density theory study of the enhanced reactivity of aza aromatic compounds participating in Diels–Alder reactions

Published:2020 Issue:2 Volume:18 Page:292-304
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Domingo Luis R.¹²³⁴^ORCID,Ríos-Gutiérrez Mar¹²³⁴⁵^ORCID,Pérez Patricia⁶⁷⁸⁹¹⁰^ORCID

Affiliation:

1. Department of Organic Chemistry

2. University of Valencia

3. 46100 Burjassot

4. Spain

5. Department of Chemistry and Chemical Biology

6. Universidad Andres Bello

7. Facultad de Ciencias Exactas

8. Departamento de Ciencias Químicas

9. Computational and Theoretical Chemistry Group

10. 8370146 Santiago

Abstract

The change of C–H by N: in these aromatic compounds decreases the ring electron density (RED), thus decreasing the activation energies of the aza Diels–Alder reactions mainly by the loss of the aromatic character of the reagents.

Funder

Ministerio de Economía y Competitividad

Fondo Nacional de Desarrollo Científico y Tecnológico

H2020 Marie Skłodowska-Curie Actions

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/C9OB02467K

Reference62 articles.

1. Synthesen in der hydroaromatischen Reihe

2. W. Carruthers , Some Modern Methods of Organic Synthesis , Cambridge University Press , Cambridge , 2nd edn, 1978

3. W. Carruthers , Cycloaddition Reactions in Organic Synthesis , Pergamon , Oxford , 1990

4. The Conservation of Orbital Symmetry

5. F. A. Carey and R. J.Sundberg , Advanced Organic Chemistry. Part A: Strucutre and Mechanisms , Springer , New York , 5th edn, 2007

Cited by 24 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors;International Journal of Molecular Sciences;2024-06-20

2. Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions;Topics in Current Chemistry;2024-05-10

3. A computational study of 1,3-dipolar cycloadditions of nitrile oxides with dienes;Tetrahedron;2023-06

4. Exploring the Relationship between Reactivity and Electronic Structure in Isorhodanine Derivatives Using Computer Simulations;Molecules;2023-03-03

5. A molecular electron density theory study on the Chichibabin reaction: The origin of regioselectivity;Journal of Molecular Graphics and Modelling;2022-11