Thermochemistry of cyclobutadiene and tetrahedrane: A high-level computational study

Mikhail N. Glukhovtsev; Sergei Laiter; Addy Pross

doi:10.1021/j100018a012

Thermochemistry of cyclobutadiene and tetrahedrane: A high-level computational study

Mikhail N. Glukhovtsev, Sergei Laiter, Addy Pross

Department of Chemistry

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Abstract

The thermochemical properties of cyclobutadiene and tetrahedrane have been calculated using high-level MO calculations at the G2 level of theory. Enthalpies of formation of cyclobutadiene and tetrahedrane at 298 K are calculated to be 426 ± 4 and 535 ± 4 kJ mol^-1, respectively. Antiaromatic destabilization of cyclobutadiene and the strain energy of tetrahedrane have been estimated to be 170 ± 7 and 571 ± 4 kJ mol^-1 (at 298 K), respectively. The value of the antiaromatic destabilization of cyclobutadiene (42.5 kJ mol^-1) per π electron is larger than the aromatic stabilization of benzene per π electron (15.4 kJ mol^-1).

Original language	English
Pages (from-to)	6828-6831
Number of pages	4
Journal	Journal of Physical Chemistry
Volume	99
Issue number	18
DOIs	https://doi.org/10.1021/j100018a012
State	Published - 1 Jan 1995

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Physical and Theoretical Chemistry

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title = "Thermochemistry of cyclobutadiene and tetrahedrane: A high-level computational study",

abstract = "The thermochemical properties of cyclobutadiene and tetrahedrane have been calculated using high-level MO calculations at the G2 level of theory. Enthalpies of formation of cyclobutadiene and tetrahedrane at 298 K are calculated to be 426 ± 4 and 535 ± 4 kJ mol-1, respectively. Antiaromatic destabilization of cyclobutadiene and the strain energy of tetrahedrane have been estimated to be 170 ± 7 and 571 ± 4 kJ mol-1 (at 298 K), respectively. The value of the antiaromatic destabilization of cyclobutadiene (42.5 kJ mol-1) per π electron is larger than the aromatic stabilization of benzene per π electron (15.4 kJ mol-1).",

author = "Glukhovtsev, {Mikhail N.} and Sergei Laiter and Addy Pross",

year = "1995",

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doi = "10.1021/j100018a012",

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TY - JOUR

T1 - Thermochemistry of cyclobutadiene and tetrahedrane

T2 - A high-level computational study

AU - Glukhovtsev, Mikhail N.

AU - Laiter, Sergei

AU - Pross, Addy

PY - 1995/1/1

Y1 - 1995/1/1

N2 - The thermochemical properties of cyclobutadiene and tetrahedrane have been calculated using high-level MO calculations at the G2 level of theory. Enthalpies of formation of cyclobutadiene and tetrahedrane at 298 K are calculated to be 426 ± 4 and 535 ± 4 kJ mol-1, respectively. Antiaromatic destabilization of cyclobutadiene and the strain energy of tetrahedrane have been estimated to be 170 ± 7 and 571 ± 4 kJ mol-1 (at 298 K), respectively. The value of the antiaromatic destabilization of cyclobutadiene (42.5 kJ mol-1) per π electron is larger than the aromatic stabilization of benzene per π electron (15.4 kJ mol-1).

AB - The thermochemical properties of cyclobutadiene and tetrahedrane have been calculated using high-level MO calculations at the G2 level of theory. Enthalpies of formation of cyclobutadiene and tetrahedrane at 298 K are calculated to be 426 ± 4 and 535 ± 4 kJ mol-1, respectively. Antiaromatic destabilization of cyclobutadiene and the strain energy of tetrahedrane have been estimated to be 170 ± 7 and 571 ± 4 kJ mol-1 (at 298 K), respectively. The value of the antiaromatic destabilization of cyclobutadiene (42.5 kJ mol-1) per π electron is larger than the aromatic stabilization of benzene per π electron (15.4 kJ mol-1).

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U2 - 10.1021/j100018a012

DO - 10.1021/j100018a012

M3 - Article

AN - SCOPUS:0001090270

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SP - 6828

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JO - Journal of Physical Chemistry

JF - Journal of Physical Chemistry

IS - 18

ER -

Thermochemistry of cyclobutadiene and tetrahedrane: A high-level computational study

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