π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

Luis R. Domingo; Patricia Pérez; Renato Contreras

doi:10.1002/ejoc.200500466

π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

Luis R. Domingo, Patricia Pérez, Renato Contreras

Facultad Ciencias Exactas

Resultado de la investigación: Contribución a una revista › Artículo › revisión exhaustiva

27 Citas (Scopus)

Resumen

Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the C^sp3-C^sp-C^sp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers.

Idioma original	Inglés
Páginas (desde-hasta)	498-506
Número de páginas	9
Publicación	European Journal of Organic Chemistry
N.º	2
DOI	https://doi.org/10.1002/ejoc.200500466
Estado	Publicada - 16 ene. 2006

Áreas temáticas de ASJC Scopus

Química física y teórica
Química orgánica

Acceder al documento

10.1002/ejoc.200500466

Otros archivos y enlaces

Enlace a la publicación en Scopus

Citar esto

@article{5af2694171cb4ad192f1d894c23071c0,

title = "π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers",

abstract = "Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the Csp3-Csp-Csp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers.",

keywords = "Cycloadditions, Cycloalkynes, Density functional calculations, Electrophilicity, Strain",

author = "Domingo, {Luis R.} and Patricia P{\'e}rez and Renato Contreras",

year = "2006",

month = jan,

day = "16",

doi = "10.1002/ejoc.200500466",

language = "English",

pages = "498--506",

journal = "Justus Liebigs Annalen der Chemie",

issn = "0075-4617",

publisher = "Wiley-VCH Verlag",

number = "2",

}

TY - JOUR

T1 - π-strain-induced electrophilicity in small cycloalkynes

T2 - A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

AU - Domingo, Luis R.

AU - Pérez, Patricia

AU - Contreras, Renato

PY - 2006/1/16

Y1 - 2006/1/16

N2 - Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the Csp3-Csp-Csp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers.

AB - Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the Csp3-Csp-Csp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers.

KW - Cycloadditions

KW - Cycloalkynes

KW - Density functional calculations

KW - Electrophilicity

KW - Strain

UR - http://www.scopus.com/inward/record.url?scp=31144457539&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200500466

DO - 10.1002/ejoc.200500466

M3 - Article

AN - SCOPUS:31144457539

SN - 0075-4617

SP - 498

EP - 506

JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

IS - 2

ER -

π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

Resumen

Áreas temáticas de ASJC Scopus

Acceder al documento

Otros archivos y enlaces

Huella

Citar esto