On the stability of large [4n]annulenes

Chaitanya S. Wannere; Damian Moran; Norman L. Allinger; B. Andes Hess; Lawrence J. Schaad; Paul Von Ragué Schleyer

doi:10.1021/ol034979f

On the stability of large [4n]annulenes

Chaitanya S. Wannere, Damian Moran, Norman L. Allinger, B. Andes Hess, Lawrence J. Schaad, Paul Von Ragué Schleyer^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

113 Citations (Scopus)

Abstract

(Matrix presented) The stabilization energies (B3LYP/6-31G*) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n π-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the π-electron interactions. Cyclooctatetraene prefers the "tub" conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n π-electrons is revealed best by their magnetic properties rather than by their energies.

Original language	English
Pages (from-to)	2983-2986
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	17
DOIs	https://doi.org/10.1021/ol034979f
Publication status	Published - 21 Aug 2003
Externally published	Yes

Access to Document

10.1021/ol034979f

Cite this

@article{ffacce974eb14f82bb17e5eb21001aa6,

title = "On the stability of large [4n]annulenes",

abstract = "(Matrix presented) The stabilization energies (B3LYP/6-31G*) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n π-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the π-electron interactions. Cyclooctatetraene prefers the {"}tub{"} conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n π-electrons is revealed best by their magnetic properties rather than by their energies.",

author = "Wannere, {Chaitanya S.} and Damian Moran and Allinger, {Norman L.} and Hess, {B. Andes} and Schaad, {Lawrence J.} and Schleyer, {Paul Von Ragu{\'e}}",

year = "2003",

month = aug,

day = "21",

doi = "10.1021/ol034979f",

language = "English",

volume = "5",

pages = "2983--2986",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - On the stability of large [4n]annulenes

AU - Wannere, Chaitanya S.

AU - Moran, Damian

AU - Allinger, Norman L.

AU - Hess, B. Andes

AU - Schaad, Lawrence J.

AU - Schleyer, Paul Von Ragué

PY - 2003/8/21

Y1 - 2003/8/21

N2 - (Matrix presented) The stabilization energies (B3LYP/6-31G*) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n π-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the π-electron interactions. Cyclooctatetraene prefers the "tub" conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n π-electrons is revealed best by their magnetic properties rather than by their energies.

AB - (Matrix presented) The stabilization energies (B3LYP/6-31G*) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n π-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the π-electron interactions. Cyclooctatetraene prefers the "tub" conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n π-electrons is revealed best by their magnetic properties rather than by their energies.

UR - http://www.scopus.com/inward/record.url?scp=0141521437&partnerID=8YFLogxK

U2 - 10.1021/ol034979f

DO - 10.1021/ol034979f

M3 - Article

C2 - 12916961

AN - SCOPUS:0141521437

SN - 1523-7060

VL - 5

SP - 2983

EP - 2986

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

On the stability of large [4n]annulenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this