σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

Damian Moran; Mariappan Manoharan; Thomas Heine; Paul Von Ragué Schleyer

doi:10.1021/ol027159w

σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

Damian Moran, Mariappan Manoharan, Thomas Heine, Paul Von Ragué Schleyer^*

^*Corresponding author for this work

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

108 Citations (Scopus)

Abstract

(Figure presented) Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal σ-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(σ) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., σ-antiaromatic).

Original language	English
Pages (from-to)	23-26
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	1
DOIs	https://doi.org/10.1021/ol027159w
Publication status	Published - 9 Jan 2003
Externally published	Yes

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title = "σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings",

abstract = "(Figure presented) Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal σ-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(σ) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., σ-antiaromatic).",

author = "Damian Moran and Mariappan Manoharan and Thomas Heine and Schleyer, \{Paul Von Ragu{\'e}\}",

year = "2003",

month = jan,

day = "9",

doi = "10.1021/ol027159w",

language = "English",

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pages = "23--26",

journal = "Organic Letters",

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T1 - σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

AU - Moran, Damian

AU - Manoharan, Mariappan

AU - Heine, Thomas

AU - Schleyer, Paul Von Ragué

PY - 2003/1/9

Y1 - 2003/1/9

N2 - (Figure presented) Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal σ-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(σ) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., σ-antiaromatic).

AB - (Figure presented) Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal σ-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(σ) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., σ-antiaromatic).

UR - https://www.scopus.com/pages/publications/0012489685

U2 - 10.1021/ol027159w

DO - 10.1021/ol027159w

M3 - Article

C2 - 12509881

AN - SCOPUS:0012489685

SN - 1523-7060

VL - 5

SP - 23

EP - 26

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

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