Carbon‐13 chemical shifts of bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives

Lippmaa, É.; Pehk, Tõnis; Belikova, N. A.; Бобылева, А. А.; Kalinichenko, A. N.; Ordubadi, M. D.; Platé, A. F.

doi:10.1002/mrc.1270080204

Cited by 46 publications

(15 citation statements)

References 15 publications

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“…Moreover in bicyclo[3.2.1]octanols 9 with exo-OH groups,22,23 the c-carbons have signiÐcant low-frequency shifts compared with their endo counterparts 10, irrespective of the presence of a geminally substituted methyl group. 22 Here, shifts of a similar magnitude are seen (Table 2) for of both 5 and the minor product compared with C 2 C 2 in 4, consistent with exo-OH groups at in 5 and the C 4 O shading and each spin system is linked by a distinctive dashed line for which the relevant structure is given next to the resonance assigned to Remote connectivity peaks (located away from the dashed lines) are identified with their appropriate structure numbers. H 7endo .…”

Section: Characterization Of Bu †Er Solutionssupporting

confidence: 71%

NMR Characterization of3,6-Dioxa-8-azabicyclo[3.2.1]octanes andN-[Tris(hydroxymethyl)methyl]alanine Formedfrom Methylglyoxal in Tris Buffer Solutions

Bubb

1997

Magn. Reson. Chem.

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Section: Characterization Of Bu †Er Solutionssupporting

confidence: 71%

NMR Characterization of3,6-Dioxa-8-azabicyclo[3.2.1]octanes andN-[Tris(hydroxymethyl)methyl]alanine Formedfrom Methylglyoxal in Tris Buffer Solutions

Bubb

1997

Magn. Reson. Chem.

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“…Although the correspondence is not exact, substituent effects established for substituted n~rbornanes,-~ correctly predict the trends in the chemical shifts observed for the chlorinated polycyclodiene pesticides. For example, comparison of norbornane with norbornene shows that the introduction of a carboncarbon double bond between carbons 5 and 6 results in downfield shifts of 5.5, 109.0 and 11.0 ppm for carbons 1, 5 and 7 and an upfield shift of 3.5 ppm for C-2, respectively (standard norbornane numbering ~y s t e m ) .~ A similar comparison of dihydroaldrin (9) 5 6 .…”

Section: Discussionmentioning

confidence: 96%

Carbon‐13 NMR spectra of some chlorinated polycyclodiene pesticides

Cox

McKinney

1978

Org. Magn. Reson.

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~~Carbon-13 NMR spectra have been obtained for aldrin, dieldrin, isodrin, endrin, heptachlor, heptachlor oxide and 24 of theii degradationlconversion products. Chemical shifts were assigned on the basis of (1) comparison among the spectra, (2) single frequency, off-resonance decoupling experiments, (3) substituent effects derived for norbornanes and (4) spectra obtained with an added lanthanide shat reagent. The substituent effects previously reported for norbornanes were found to be applicable for establishing trends in the chemical shifts for many of the compounds studied.

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“…There have been many measurements of the chemical shifts [60][61][62] of carbon and protons in norbornane, examples of which are the work of Abraham and co-workers 60 and Lippmaa et al 61 We used the localized orbital/local origin ͑LORG͒, 63 C chemical shifts than the IGLO method, particularly for the proton spectrum. However, it appears that when a correlated wave function is used, the GIAO approach provides the best agreement with experiment.…”

Section: Nmr Propertiesmentioning

confidence: 99%

Norbornane: An investigation into its valence electronic structure using electron momentum spectroscopy, and density functional and Green’s function theories

Knippenberg

Nixon

Brunger

et al. 2004

The Journal of Chemical Physics

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We report on the results of an exhaustive study of the valence electronic structure of norbornane (C 7 H 12 ), up to binding energies of 29 eV. Experimental electron momentum spectroscopy and theoretical Green's function and density functional theory approaches were all utilized in this investigation. A stringent comparison between the electron momentum spectroscopy and theoretical orbital momentum distributions found that, among all the tested models, the combination of the Becke-Perdew functional and a polarized valence basis set of triple-quality provides the best representation of the electron momentum distributions for all of the 20 valence orbitals of norbornane. This experimentally validated quantum chemistry model was then used to extract some chemically important properties of norbornane. When these calculated properties are compared to corresponding results from other independent measurements, generally good agreement is found. Green's function calculations with the aid of the third-order algebraic diagrammatic construction scheme indicate that the orbital picture of ionization breaks down at binding energies larger than 22.5 eV. Despite this complication, they enable insights within 0.2 eV accuracy into the available ultraviolet photoemission and newly presented (e,2e) ionization spectra, except for the band associated with the 1a 2 Ϫ1 one-hole state, which is probably subject to rather significant vibronic coupling effects, and a band at ϳ25 eV characterized by a momentum distribution of ''s-type'' symmetry, which Green's function calculations fail to reproduce. We note the vicinity of the vertical double ionization threshold at ϳ26 eV.

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Carbon‐13 chemical shifts of bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives

Cited by 46 publications

References 15 publications

NMR Characterization of3,6-Dioxa-8-azabicyclo[3.2.1]octanes andN-[Tris(hydroxymethyl)methyl]alanine Formedfrom Methylglyoxal in Tris Buffer Solutions

NMR Characterization of3,6-Dioxa-8-azabicyclo[3.2.1]octanes andN-[Tris(hydroxymethyl)methyl]alanine Formedfrom Methylglyoxal in Tris Buffer Solutions

Carbon‐13 NMR spectra of some chlorinated polycyclodiene pesticides

Norbornane: An investigation into its valence electronic structure using electron momentum spectroscopy, and density functional and Green’s function theories

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