Folding of the Selenanthren Molecule

Wood, R.G.; Williams, Gordon

doi:10.1038/150321a0

Cited by 8 publications

(3 citation statements)

References 3 publications

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“…They also made the rather unexpected observation that the Se-C bond length in this compound is extraordinarily long, 2.01 ± 0.03 Á.; this is 0.07 A. longer than the sum of the single-bond covalent radii for selenium and carbon. The crystal structures of selenanthrene (352,354) and phenoxaselenin (353) have been determined. From the data Wood and Williams (354) have calculated that the angle of fold in selenanthrene is about 127°.…”

Section: Table 18mentioning

confidence: 99%

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Some Aspects of the Organic Chemistry of Selenium.

Campbell¹,

Walker²,

Coppinger³

1952

Chem. Rev.

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Section: Table 18mentioning

confidence: 99%

“…The crystal structures of selenanthrene (352,354) and phenoxaselenin (353) have been determined. From the data Wood and Williams (354) have calculated that the angle of fold in selenanthrene is about 127°.…”

Section: Table 18mentioning

confidence: 99%

Some Aspects of the Organic Chemistry of Selenium.

Campbell¹,

Walker²,

Coppinger³

1952

Chem. Rev.

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“…Notably, the first crystallographic study of 1 was performed in 1942, and while the study did not determine a complete structure, the authors attempted to estimate the dihedral angle between the phenyl rings of 1 . In 1988, a full structure of 1 was published, but it was only refined isotropically .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Larson,

Boyle,

Labrecque

et al. 2024

Inorg. Chem.

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The use of new dynamic scaffolds for constructing inorganic and organometallic complexes with enhanced reactivities is an important new research direction. Toward this fundamental aim, an improved synthesis of the dynamic scaffold selenanthrene, along with its monoxide, trans-dioxide and the previously unknown trioxide, is reported. A discussion of the potential reaction mechanism for selenanthrene is provided, and all products were characterized using 1 H, 13 C, and 77 Se nuclear magnetic resonance (NMR) spectroscopy and single-crystal X-ray crystallography. The dynamic ring inversion processes (i.e., "butterfly motion") for selenanthrene and its oxides were investigated using variabletemperature 1 H NMR and density functional theory calculations. The findings suggest that selenanthrene possesses a roughly equal barrier to inversion as its sulfur analogue, thianthrene. However, selenanthrene oxides evidently possess larger inversion barriers as compared to their sulfur analogues due to the enhanced electrostatic intramolecular interactions inherent between the highly polar selenium−oxygen bond and adjacent C−H moieties. Finally, we propose a quantitative "flexibility index" in deg/(kcal/mol) for various tricyclic scaffolds to provide researchers with a comparative scale of dynamic motion across many different systems.

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Ring Systems Containing Selenium and Tellurium

1966

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Folding of the Selenanthren Molecule

Cited by 8 publications

References 3 publications

Some Aspects of the Organic Chemistry of Selenium.

Some Aspects of the Organic Chemistry of Selenium.

Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds

Ring Systems Containing Selenium and Tellurium

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