<sup>13</sup>C, <sup>13</sup>C coupling constants in anthracene, 9,10‐dihydroanthracene and phthalic acid derivatives. Determination of signs by the symmetrical double labelling (SDL) method V

Hansen, Poul Erik; Berg, Arne

doi:10.1002/mrc.1270120111

Cited by 15 publications

(6 citation statements)

References 26 publications

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“…It is also obvious that the label is in the aromatic ring as judged from the fact that 77, 91 and 105 of the unlabelled sample has now become partly 78, 92 and 106. This is confirmed in the 13 C NMR spectrum, which shows a very strong resonance at 134 ppm, the carbon ascribed to C- No correlations could be observed.…”

Section: Resultssupporting

confidence: 79%

“…Judging from the 13 C carbon spectrum (see later) the label is at carbon C-3 0 (Figure 1). The structure of the follower (2) is assigned by MS ( Figure 3) and 2D NMR.…”

Section: Resultsmentioning

confidence: 99%

“…Acetylation using acetic anhydride 13 C enriched at the carbonyl carbon leads to incorporation at the aromatic ring. Judging from the 13 C carbon spectrum (see later) the label is at carbon C-3 0 (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…Deuteriation of the latter also means that the two protons at C-4 (2.50 and 2.25 ppm) are now doublets in the 1 H NMR spectrum as the homoallylic coupling to the methyl group at C-6 has disappeared. In the 13 C spectrum the resonances at 23.92 and 30.11 ppm disappear. Unfortunately, the S/N ratio is too low to see the resonances from the deuteriated carbons (see Figure 1 for cedrene (3)).…”

Section: Deuteriationmentioning

confidence: 86%

“…The organic solvent was evaporated under reduced pressure and the oil residue was chromatographed on silica gel, using dichloromethane as eluent to give the acetyl cedrene-d 4 (1.45 g) as a light-amber colored oil. 13 Figure 5). …”

Section: Acetyl Cedrene-dmentioning

confidence: 92%

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Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Kamounah

Christensen

Hansen

2010

Labelled Comp Radiopharmac

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Acetylation of cedarwood oil (Virginia) leads besides acetyl cedrene also to a minor product, 1,7,7‐trimethyl‐2,3‐(3′,4′‐dimethylbenzo)bicyclo[3.2.1]octane (follower). This product is identified by 2D NMR. Acetylation of cedarwood oil with 13C‐1 labeled acetic acid anhydride leads to a product labeled at the aromatic carbon C‐3′. From the 13C‐labeled compound 13C‐13C coupling constants could be measured.Acetyl cedrene is conveniently deuteriated by an acid‐catalysed exchange reaction using trifluoroacetic anhydride and D2O. The product is found to be deuteriated both at the acetyl group and at the methyl group at the double bond (carbon 6).The reaction condition during deuteriation of cedrol leads to the elimination of the hydroxyl group at C‐6 with the formation of α‐cedrene deuteriated at H‐5 and the methyl group at C‐6.Deuteriation of the follower leads to deuterium exchange at the aromatic carbons C‐5′ and C‐6′. Copyright © 2010 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 79%

“…Judging from the 13 C carbon spectrum (see later) the label is at carbon C-3 0 (Figure 1). The structure of the follower (2) is assigned by MS ( Figure 3) and 2D NMR.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Deuteriationmentioning

confidence: 86%

Section: Acetyl Cedrene-dmentioning

confidence: 92%

See 3 more Smart Citations

Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Kamounah

Christensen

Hansen

2010

Labelled Comp Radiopharmac

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Synthesis and NMR spectrum of [¹³C₁₈]‐meso‐hexestrol, a fully carbon‐13 substituted ligand for NMR studies of the estrogen receptor

Kochanny

Härd

Katzenellenbogen

1993

Magnetic Reson in Chemistry

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The estrogen receptor ligand meso-hexestrol has been synthesized with "C enrichment (98 at.%) at every position. I3C NMR spectra of the intermediates were obtained and i3C-13C coupling patterns analyzed. The complex I3C NMR spectrum of 1 13C,,I-meso-hexestro1 was simplified through the use of selective I3C decoupling. Severa1 13C-13C coupling constants were estimated from the decoupled spectra and refined via iterative simulation. Some additional coupling constants were measured in selective one-dimensional "C COSY spectra. Coupling constants are reported to an accuracy of f0.4-1 Hz. This study demonstrates the feasibility of determining l3C-I3C coupling constants in highly 13C-substituted compounds; such compounds are expected to be used with increased frequency in studying receptor-ligand interactions by polarization transfer methods.

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¹³C NMR of polycyclic aromatic compounds. A review

Hansen

1979

Org. Magn. Reson.

163

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ContentsThe analysis of the =C NMR spectra o€ polycyclic aromatics is discussed briefly. Basic trends of chemical shats are mentioned, but the emphasis is placed on substituent-induced chemical s b h (SCS). Sembempmcal approaches and regressional analysis are treated. The factors controlling SCS are discussed and steric, mesomeric and winducthe effects are analysed.CH, CF, CC, CP and C, Metal coupling constants are investigated and the influence of steric effects, bond order, mesomerism and angle distortions in relation to some of these coupling constants is discussed. Relaxation times are desmhd in a series of compounds. The effects of dissolved oxygen or radicals are shown and the use of TI as a monitor of molecular tumbling is depicted. The impact of "C NMR on the understanding of charged aromatic species, both positive and negative ions, is mentioned and new information about reaction intermediates in electrophilic aromatic substitution is outlined. The possibility of using "C NMR to investigate charge transfer complexes is also discussed. Among other subjects treated are automerization, deuterium exchange and biosynthetic incorporation of labelled materials and, finally, quantitative &yis is briefly touched upon.

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¹³C, ¹³C coupling constants in anthracene, 9,10‐dihydroanthracene and phthalic acid derivatives. Determination of signs by the symmetrical double labelling (SDL) method V

Cited by 15 publications

References 26 publications

Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Synthesis and NMR spectrum of [¹³C₁₈]‐meso‐hexestrol, a fully carbon‐13 substituted ligand for NMR studies of the estrogen receptor

¹³C NMR of polycyclic aromatic compounds. A review

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13C, 13C coupling constants in anthracene, 9,10‐dihydroanthracene and phthalic acid derivatives. Determination of signs by the symmetrical double labelling (SDL) method V

Cited by 15 publications

References 26 publications

Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Acetyl cedrene and its follower. An Isotopic, NMR and MS Structure elucidation and deuteriation study

Synthesis and NMR spectrum of [13C18]‐meso‐hexestrol, a fully carbon‐13 substituted ligand for NMR studies of the estrogen receptor

13C NMR of polycyclic aromatic compounds. A review

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¹³C, ¹³C coupling constants in anthracene, 9,10‐dihydroanthracene and phthalic acid derivatives. Determination of signs by the symmetrical double labelling (SDL) method V

Synthesis and NMR spectrum of [¹³C₁₈]‐meso‐hexestrol, a fully carbon‐13 substituted ligand for NMR studies of the estrogen receptor

¹³C NMR of polycyclic aromatic compounds. A review