1H NMR spectra of monosubstituted phenanthrenes

Balo, Carmen; Fernández, Fernando Nieto; González, Carmen; López, Carmen

doi:10.1016/0584-8539(94)80142-8

Cited by 7 publications

(5 citation statements)

References 12 publications

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“…19 F NMR data have been reported for 1b, 13 -15 3b, 13,14,16 4b, 13 4c, 13 5b 16 and 6b. 13 26 Here, we report a complete NMR analysis of these compounds, which are characterized by 1 H, 13 C, 19 F, 1 H-1 H-COSY, 2D J-resolved 1 H and 1 H-13 C HMBC NMR spectroscopy (400 and 500 MHz, CDCl 3 ), and compared with NMR data for the corresponding parent PAHs (1a-8a). Suitable NMR reference data obtained in CDCl 3 were found in the literature only for naphthalene (1a), 27 fluorene (2a) 22,25 and chrysene (7a).…”

Section: As Markers For In Vivo Metabolism Studied In the Terrestriamentioning

confidence: 99%

Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy

Lutnæs

Luthe²,

Brinkman³

et al. 2005

Magnetic Reson in Chemistry

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Monofluorinated polycyclic aromatic hydrocarbons (F-PAHs) have attracted much attention in analytical, environmental, toxicological and mechanistic studies because of their physico-chemical properties, which are closely similar to those of the parent PAHs. Because of this, full NMR characterization has become of interest. Complete 1H, 13C and 19F NMR chemical shifts, and also 1J(H,C), (n)J(C,F), (n)J(H,F) and (n)J(H,H) coupling constants, have been assigned for the F-PAHs 1-fluoronaphthalene, 2-fluorofluorene, 5-fluoroacenaphthylene, 2-fluorophenanthrene, 3-fluorophenanthrene, 3-fluorofluoranthene, 1-fluoropyrene, 1-fluorochrysene, 2-fluorochrysene, 3-fluorochrysene and 9-fluorobenzo[k]fluoranthene. To allow comparison with the corresponding parent PAHs, the 1H and 13C chemical shifts of acenaphthylene, phenanthrene, fluoranthene, pyrene and benzo[k]fluoranthene were determined. Chemical shift increments and the effects on the coupling constants from the fluorine substitution are discussed.

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Section: As Markers For In Vivo Metabolism Studied In the Terrestriamentioning

confidence: 99%

Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy

Lutnæs

Luthe²,

Brinkman³

et al. 2005

Magnetic Reson in Chemistry

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“…A test of the experimental validity of Eqns ( and ) is provided in Fig. by comparing the creation–reconversion efficiency of 4Q‐coherence in phenanthrene, a molecule for which a very precise description of the spin system is available in the literature, recorded for a series of values of the τ delay. Figure compares simulations and experimental intensity of 4Q‐filtered 1 H spectra of this molecular system up to a value of τ that can be still reasonably used in a 2D experiment.…”

Section: Resultsmentioning

confidence: 99%

Improved excitation uniformity in multiple‐quantum NMR experiments of mixtures

Reddy

Caldarelli

2013

Magnetic Reson in Chemistry

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Multiple-quantum (1)H NMR spectroscopy has been finding a renewed interest for its possible applications in the analysis of mixtures of small molecules, due to its simplification properties. A crucial aspect of this application of multiple-quantum NMR is the sensitivity of the spectrum intensity to the molecular structure and to the parameterization of the experiment, which could result in the missing of some components. We demonstrate that a general scheme to overcome this drawback consists in varying the experiment parameterizations over a small number of values, selected according the values of the couplings and the relaxation rates.

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“…The 1 H-1 H coupling constants are comparable to those presented in the literature. 4,7,9 The signs of couplings were adopted from work of Laatikainen on the spin-spin couplings of naphthalene. 9 The sign of 5 J H4,H5 (assumed positive) was evaluated with PERCH by changing it to negative, but no effect on the spectrum was seen.…”

Section: Resultsmentioning

confidence: 99%

Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

Sipilä¹,

Kansikas²,

Mesilaakso³

1999

J. Chem. Soc., Perkin Trans. 2

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The crystal structures of 9-phenylthiophenanthrene (C 20 H 14 S) and 9-tert-butylthiophenanthrene (C 18 H 18 S) were determined at 193 K. The former crystallizes in orthorhombic space group P2 1 2 1 2 1 (No. 19) with cell dimensions a = 5.602( 2), b = 9.247(3), and c = 27.508(12) Å and the latter in orthorhombic space group Pbcn (No. 60) with cell parameters a = 21.335(4), b = 7.540(2), and c = 18.197(4) Å. In both compounds the substituents at sulfur are nearly perpendicular to the phenanthrene plane. NMR spectra of the compounds were recorded in CDCl 3 . The 1 H NMR spectral parameters were analyzed in detail by using an iterative spectral analysis program. The 13 C{ 1 H} resonances were fully assigned with the aid of two-dimensional heteronuclear chemical shift correlation spectra. On the basis of the NOE difference spectra the orientation of the side chain was concluded to be similar to that in the solid state.

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1H NMR spectra of monosubstituted phenanthrenes

Cited by 7 publications

References 12 publications

Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy

Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy

Improved excitation uniformity in multiple‐quantum NMR experiments of mixtures

Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

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1H NMR spectra of monosubstituted phenanthrenes

Cited by 7 publications

References 12 publications

Characterization of monofluorinated polycyclic aromatic compounds by 1H, 13C and 19F NMR spectroscopy

Characterization of monofluorinated polycyclic aromatic compounds by 1H, 13C and 19F NMR spectroscopy

Improved excitation uniformity in multiple‐quantum NMR experiments of mixtures

Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

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Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy

Characterization of monofluorinated polycyclic aromatic compounds by ¹H, ¹³C and ¹⁹F NMR spectroscopy