Torsional Angles in Vinylarenes Determined by High-Field NMR Spectroscopy

Kevin L. Facchine; Stuart W. Staley; Peter C.M. Van Zijl; Prasanna K. Mishra; Aksel A. Bothner-By

doi:10.1021/ja00223a005

Torsional Angles in Vinylarenes Determined by High-Field NMR Spectroscopy

Kevin L. Facchine, Stuart W. Staley, Peter C.M. Van Zijl, Prasanna K. Mishra, Aksel A. Bothner-By

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

Abstract

High-resolution deuterium NMR spectra of styrene-α-d, styrene-d_g, 1-vinylnaphthalene-α-d, and 2-vinylnaphthalene-α-d in hydrocarbon solvents were recorded at field strengths of 14.11 to 14.57 T. Quadrupolar splittings were observed as a consequence of magnetic field-induced alignment of the solute molecules. The magnitudes of the splittings were used to calculate the average value of sin² α, where α is the dihedral angle between the vinyl and ring planes; α_rms = sin^-1 (sin² α)^1/2 was 16.5 ± 0.9° for styrene, 18.3 ± 3.1° for 2-vinylnaphthalene, and 41.8 ± 4.1° for 1-vinylnaphthalene. The styrene value was used to deduce the magnitude of the twofold rotational barrier and the extent of steric destabilization of the planar form. The results are compared with available literature data.

Original language	English (US)
Pages (from-to)	4900-4905
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	110
Issue number	15
DOIs	https://doi.org/10.1021/ja00223a005
State	Published - Jul 1988
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00223a005

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@article{24bc84c812264bb8a87dd8413977b70c,

title = "Torsional Angles in Vinylarenes Determined by High-Field NMR Spectroscopy",

abstract = "High-resolution deuterium NMR spectra of styrene-α-d, styrene-dg, 1-vinylnaphthalene-α-d, and 2-vinylnaphthalene-α-d in hydrocarbon solvents were recorded at field strengths of 14.11 to 14.57 T. Quadrupolar splittings were observed as a consequence of magnetic field-induced alignment of the solute molecules. The magnitudes of the splittings were used to calculate the average value of sin2 α, where α is the dihedral angle between the vinyl and ring planes; αrms = sin-1 (sin2 α)1/2 was 16.5 ± 0.9° for styrene, 18.3 ± 3.1° for 2-vinylnaphthalene, and 41.8 ± 4.1° for 1-vinylnaphthalene. The styrene value was used to deduce the magnitude of the twofold rotational barrier and the extent of steric destabilization of the planar form. The results are compared with available literature data.",

author = "Facchine, {Kevin L.} and Staley, {Stuart W.} and {Van Zijl}, {Peter C.M.} and Mishra, {Prasanna K.} and Bothner-By, {Aksel A.}",

year = "1988",

month = jul,

doi = "10.1021/ja00223a005",

language = "English (US)",

volume = "110",

pages = "4900--4905",

journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Torsional Angles in Vinylarenes Determined by High-Field NMR Spectroscopy

AU - Facchine, Kevin L.

AU - Staley, Stuart W.

AU - Van Zijl, Peter C.M.

AU - Mishra, Prasanna K.

AU - Bothner-By, Aksel A.

PY - 1988/7

Y1 - 1988/7

N2 - High-resolution deuterium NMR spectra of styrene-α-d, styrene-dg, 1-vinylnaphthalene-α-d, and 2-vinylnaphthalene-α-d in hydrocarbon solvents were recorded at field strengths of 14.11 to 14.57 T. Quadrupolar splittings were observed as a consequence of magnetic field-induced alignment of the solute molecules. The magnitudes of the splittings were used to calculate the average value of sin2 α, where α is the dihedral angle between the vinyl and ring planes; αrms = sin-1 (sin2 α)1/2 was 16.5 ± 0.9° for styrene, 18.3 ± 3.1° for 2-vinylnaphthalene, and 41.8 ± 4.1° for 1-vinylnaphthalene. The styrene value was used to deduce the magnitude of the twofold rotational barrier and the extent of steric destabilization of the planar form. The results are compared with available literature data.

AB - High-resolution deuterium NMR spectra of styrene-α-d, styrene-dg, 1-vinylnaphthalene-α-d, and 2-vinylnaphthalene-α-d in hydrocarbon solvents were recorded at field strengths of 14.11 to 14.57 T. Quadrupolar splittings were observed as a consequence of magnetic field-induced alignment of the solute molecules. The magnitudes of the splittings were used to calculate the average value of sin2 α, where α is the dihedral angle between the vinyl and ring planes; αrms = sin-1 (sin2 α)1/2 was 16.5 ± 0.9° for styrene, 18.3 ± 3.1° for 2-vinylnaphthalene, and 41.8 ± 4.1° for 1-vinylnaphthalene. The styrene value was used to deduce the magnitude of the twofold rotational barrier and the extent of steric destabilization of the planar form. The results are compared with available literature data.

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Torsional Angles in Vinylarenes Determined by High-Field NMR Spectroscopy

Abstract

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