13C NMR and31P NMR spectral assignment of newβ-phosphonylated hydrazones

Akacha, Azaiez Ben; Barkallah, Salim; Zantour, Hedi

doi:10.1002/(sici)1097-458x(199912)37:12<916::aid-mrc547>3.0.co;2-w

Cited by 14 publications

(2 citation statements)

References 14 publications

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“…Indeed, according to some literature data [25,[30][31][32][33][34] concerning the stereochemistry of imines, hydrazones, and oximes, the carbon atom adjacent to the C=N double bond resonates at higher fields when it is in syn position to the group on the nitrogen atom (R 3 in our case). The C2 carbon atom is characterized by two singlets in the region included between 39.0 ppm and 45.6 ppm.…”

Section: Scheme 2 Z and E Isomers In Compoundsmentioning

confidence: 53%

Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives

2015

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We report for the first time the synthesis of γ-iminophosphonates and phosphine oxides from the acidcatalysed reaction of primary amines with γ-phosphonylketones. The full characterization of these compounds through their 1 H, 31 P, and 13 C NMR spectra indicates that they are obtained as a mixture of Z and E isomers. An unambiguous method for the assignment of these configurations, based on the 13 C chemical shifts of C2 carbon atoms in the α position with respect to the C=N double bond is used. The 31 P chemical shifts are also of diagnostic importance in assigning the Z and E configurations. Indeed, the phosphorus atom is found to resonate at a slightly higher field in Z isomers.

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Section: Scheme 2 Z and E Isomers In Compoundsmentioning

confidence: 53%

Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives

2015

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“…It should be emphasized that the 31 P NMR spectrum at 298 K indicates that an equilibrium between the two forms is possible in solution; both Z and E isomers were found, with an E/Z ratio of 0.40/0.60. As for the case of the phosphonylhydrazone series (Ben Akacha et al, 1999), the equilibrium also depends on temperature. Thus, at 328 K the equilibrated content of the Z isomer decreases to 0.50.…”

Section: Commentmentioning

confidence: 99%

Ethyl 3-[1-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorin-2-yl)propan-2-ylidene]carbazate: a combined X-ray and density functional theory (DFT) study

Arfaoui

Kouass²,

Salah³

et al. 2010

Acta Crystallogr C

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In the title compound, C(11)H(21)N(2)O(5)P, one of the two carbazate N atoms is involved in the C=N double bond and the H atom of the second N atom is engaged in an intramolecular hydrogen bond with an O atom from the dimethylphosphorin-2-yl group, which is in an uncommon cis position with respect to the carbamate group. The cohesion of the crystal structure is also reinforced by weak intermolecular hydrogen bonds. Density functional theory (DFT) calculations at the B3LYP/6-311++g(2d,2p) level revealed the lowest energy structure to have a Z configuration at the C=N bond, which is consistent with the configuration found in the X-ray crystal structure, as well as a less stable E counterpart which lies 2.0 kcal mol(-1) higher in potential energy. Correlations between the experimental and computational studies are discussed.

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X‐ray Diffraction and Solid‐State NMR Studies of a Germanium Binuclear Complex

Mafra

Paz

Shi

et al. 2005

Chemistry A European J

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A compound formulated as (C4H12N2)[Ge2(pmida)2(OH)2] x 4 H2O (where pmida(4-) = N-(phosphonomethyl)iminodiacetate and C4H12N2(2+) = piperazinedium cation), containing the anionic [Ge2(pmida)2(OH)2]2- complex, has been synthesised by the hydrothermal approach and its structure determined by single-crystal X-ray diffraction analysis. Several high-resolution solid-state magic-angle spinning (MAS) NMR techniques, in particular two-dimensional 1H-X(13C,31P) heteronuclear correlation (HETCOR) and 1H-1H homonuclear correlation (HOMCOR) experiments incorporating a frequency-switched Lee-Goldburg (FS-LG) decoupling scheme, have been employed for the first time in such a material. Using these tools in tandem affords an excellent general approach to study the structure of other inorganic-organic hybrids. We assigned the NMR resonances with the help of C...H and P...H internuclear distances obtained through systematic statistical analyses of the crystallographic data. The compound was further characterised by powder X-ray diffraction techniques, IR and Raman spectroscopy, and by elemental and thermal analyses (thermogravimetric analysis and differential scanning calorimetry).

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13C NMR and31P NMR spectral assignment of newβ-phosphonylated hydrazones

Cited by 14 publications

References 14 publications

Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives

Multinuclear NMR structural study of novel γ-iminophosphonate and phosphine oxide derivatives

Ethyl 3-[1-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorin-2-yl)propan-2-ylidene]carbazate: a combined X-ray and density functional theory (DFT) study

X‐ray Diffraction and Solid‐State NMR Studies of a Germanium Binuclear Complex

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