Sensitivity-enhanced NMR detection of nonprotonated nitrogen-15 nuclei

Bax, Ad; Niu, Chien Hua; Live, David

doi:10.1021/ja00316a074

Cited by 51 publications

(9 citation statements)

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“…The correlation between H2 and the carbonyl carbon was then demonstrated by a selective INAPT experiment (33,34), thus showing that the carbonyl carbon is two atoms away from C2. With one isomer in hand, it was then possible to prepare the bis(benzimidazo1e) derivative of trans-dibenzoperylene by a route that yields one and only one regioisomer.…”

Section: Resultsmentioning

confidence: 97%

“…Recovery times between 100 ms and 1.2 s with a recycle delay of 10 s were employed for inversion-recovery (31) relaxation experiments. The 1 3~-{ '~) selective INEPT (INAPT) spectra were recorded using a pulse sequence adapted from Bax et al (33,34); the 'H selective excitation was provided by a rectangular pulse of 25 Hz nominal width (90" pulse, 10 ms). Standard pulse sequences and phase cycling schemes (41) were used to record 'H-'H COSY (27,28) and phase-sensitive (TPPI) NOESY (29,30) spectra.…”

Section: Methodsmentioning

confidence: 99%

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Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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Abstract:The reported structure of aceanthrene green, a pigment prepared by potassium hydroxide fusion of 1.9-anthracenedicarboxylic imide, was found to be incorrect. The structure of the pigment is reassigned to 7,8,15,16-dibenzo[a j]perylenetetracarboxylic diimide on the basis of COSY, NOESY, and inversion-recovery 'H NMR experiments. N-Alkyl-or N-phenyl-l,9-anthracenedicarboxylic imides, aceanthryleno[l,2-blquinoxaline, and a benzimidazole derivative of 1,9-anthracenedicarboxylic anhydride were found to give the same dibenzo[a jlperylene structure when reacted in potassium hydroxide. The electronic spectra of these derivatives is reported and it is shown that, as predicted by Pariser-Parr-Pople calculations, they absorb in the near-infrared. Finally, a mechanistic outline for the fusion is proposed on the basis of AM1 and frontier molecular orbital calculations.Key words: photoconductor, near-infrared, aceanthrene green, alkalifusion, polycyclic aromatic hydrocarbon.RCsumC : On a trouvC que la structure proposCe anterieurement pour l'ackanthrbne vert, un pigment prCparC par fusion de l'imide de l'acide anthracbne-l,9-dicarboxylique avec de l'hydroxyde de potassium, est incorrecte. En se basant sur des expkriences COSY, NOESY et d'inversion-rCcupCration en RMN du 'H on lui a rCattribuC la structure du diimide de l'acide dibenzo[a jlpCrylbne-7,8,15,16-tCtracarboxylique. On a trouvC que par rCaction, par fusion avec de l'hydroxyde de potassium, les N-alkyl-ou N-phCnylimides de l'acide anthrackne-1,9-di-carboxylique, l'acCanthrylCno[l,2-b]quinoxaline et un dCrivC benzimidazole de l'anhydride de l'acide anthracbne-l,9-dicarboxylique conduisent tous B la m&me structure dibenzo[a jlpCrylkne. On rapporte les spectres Clectroniques de ces dCrivCs et il est montrC, tel que prCdit par des calculs de type Pariser-Parr-Pople, qu'ils absorbent dans le proche infrarouge. Enfin, en se basant sur des calculs d'orbitales molCculaires AM1 et frontibres, on propose un aperp du mCcanisme pour la fusion.Mots cles : photoconducteur, proche infrarouge, acCanthrbne vert, fusion alcaline, hydrocarbure polycyclique aromatique.[Traduit par la rCdaction]

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Section: Resultsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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“…The signals in the proton and carbon NMR spectra were correlated using a two dimensional heterocorrelated experiment: 13 C, 1 H CORR [3]. Signals from tertiary carbon atoms were accumulated and assigned using selective polarization transfer from protons having sca lar spin-spin interaction with a 13 C nucleus through several bonds (INEPT LR) [4]. Gas chromatography-mass spectrometry experi ments were carried out on an Automass 150 spectrome ter (Delsi Nermag, France) in electron impact mode (ionization energy of 70 eV).…”

Section: Hydrolysis Of Imentioning

confidence: 99%

Synthesis of 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-trithione through ethyl-(4-ethyl-5-thioxo-[1,2,4]-dithiazolidin-3-ylidene)ammonium oxopentachlorotungstate(VI) hydrolysis and the dimroth rearrangement in it on heating

et al. 2013

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We demonstrate that the previously synthesized product of ethyl isothiocyanate insertion into tungsten hexachloride, WCl 5 {N(Et)C(S)N(Et)C(S)Cl}, whose partial hydrolysis yields {N(Et)C(S)-S-S-C=NH(Et)}[WOCl 5 ] (I), can be used as a source of biologically active heterocyclic compounds. 1 H and 13 C NMR and gas chromatography-mass spectrometry data show that reaction of I with a saturated aqueous Na 2 CO 3 solution yields a number of thiazolidine heterocycles, mostly 4 ethyl 5 ethylimino [1,2,4] dithia zolidin 3 trithione. The thermal Dimroth rearrangement leads to the formation of 2,4 diethyl [1,2,4] dithi azolidin 3,5 dithione and the products of partial hydrolysis of both heterocycles: 4 ethyl 5 ethylimino [1,2,4] dithiazolidin 3 on and 2,4 diethyl 3 thioxo [1,2,4] dithiazolidin 5 on.

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“…In this 2D map, the highest-frequency cross peaks. The second uses the selective INEPT sequence 1 H cross peak near 2.40 ppm (along F 1 ) has the highest 13 C (15)(16)(17) to simplify the fluorinated carbon region. Addi-frequency near 34.2 ppm, and the lowest-frequency 1 H cross tional information on the relative signs of the heteronuclear peak near 2.32 ppm has the lowest 13 C frequency near 33.7 ppm.…”

Section: H Nmr Andmentioning

confidence: 99%

Two Strategies for NMR Spectral Simplification of Highly Fluorinated Alkyl Chains

Ribeiro

1995

Journal of Magnetic Resonance, Series A

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Sensitivity-enhanced NMR detection of nonprotonated nitrogen-15 nuclei

Cited by 51 publications

References 0 publications

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Synthesis of 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-trithione through ethyl-(4-ethyl-5-thioxo-[1,2,4]-dithiazolidin-3-ylidene)ammonium oxopentachlorotungstate(VI) hydrolysis and the dimroth rearrangement in it on heating

Two Strategies for NMR Spectral Simplification of Highly Fluorinated Alkyl Chains

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