Restricted Rotation in Hexaarylbenzenes

Devens Gust

doi:10.1021/ja00463a034

Restricted Rotation in Hexaarylbenzenes

Devens Gust

Molecular Sciences, School of (SMS)

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

78 Scopus citations

Abstract

Hexaarylbenzenes exist in a conformation in which the peripheral rings are perpendicular to the plane of the central ring on the nmr time scale. Hexaarylbenzenes substituted in ortho or meta positions of the peripheral rings display restricted rotation about the single bonds joining the central and peripheral rings, and complex stereoisomerism and stereoisomerization behavior results. The rotational barriers observed are relatively high (up to ~38 kcal/mol), and even rings bearing only a m-methyl substituent lead to barriers of ~16 kcal/mol.

Original language	English (US)
Pages (from-to)	6980-6982
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	99
Issue number	21
DOIs	https://doi.org/10.1021/ja00463a034
State	Published - Jan 1 1977

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "Hexaarylbenzenes exist in a conformation in which the peripheral rings are perpendicular to the plane of the central ring on the nmr time scale. Hexaarylbenzenes substituted in ortho or meta positions of the peripheral rings display restricted rotation about the single bonds joining the central and peripheral rings, and complex stereoisomerism and stereoisomerization behavior results. The rotational barriers observed are relatively high (up to ~38 kcal/mol), and even rings bearing only a m-methyl substituent lead to barriers of ~16 kcal/mol.",

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year = "1977",

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N2 - Hexaarylbenzenes exist in a conformation in which the peripheral rings are perpendicular to the plane of the central ring on the nmr time scale. Hexaarylbenzenes substituted in ortho or meta positions of the peripheral rings display restricted rotation about the single bonds joining the central and peripheral rings, and complex stereoisomerism and stereoisomerization behavior results. The rotational barriers observed are relatively high (up to ~38 kcal/mol), and even rings bearing only a m-methyl substituent lead to barriers of ~16 kcal/mol.

AB - Hexaarylbenzenes exist in a conformation in which the peripheral rings are perpendicular to the plane of the central ring on the nmr time scale. Hexaarylbenzenes substituted in ortho or meta positions of the peripheral rings display restricted rotation about the single bonds joining the central and peripheral rings, and complex stereoisomerism and stereoisomerization behavior results. The rotational barriers observed are relatively high (up to ~38 kcal/mol), and even rings bearing only a m-methyl substituent lead to barriers of ~16 kcal/mol.

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Restricted Rotation in Hexaarylbenzenes

Abstract

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