ChemInform Abstract: KRISTALLSTRUKTUR EINES ANTIVITAMIN K, DIPHTIOCOL

Bravic, G.; Gaultier, J.; Hauw, C.

doi:10.1002/chin.197407092

Cited by 15 publications

(28 citation statements)

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“…[1] Several products have been isolated in both basic and acidic conditions. [2] Whereas the structures of two of them, 1-(indan-1,3-dione-2-ylidene)indan-3-one (bindone, 2) and tribenzo[a,f,k]trindenone (truxenequinone, 3), [3] have been unequivocally established (the X-ray structure for 2 was reported [4] ), the chemical identities of the other products have been either controversial or have never been verified using contemporary methods of chemical analysis.…”

Section: Introductionmentioning

confidence: 99%

Self-Condensation of 1,3-Indandione: A Reinvestigation

et al. 2000

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Section: Introductionmentioning

confidence: 99%

Self-Condensation of 1,3-Indandione: A Reinvestigation

et al. 2000

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“…The other calculated chemical shifts were in excellent agreement with the experimental values (deviations within 0.1-0.2 ppm for 1 H and 2-3 ppm for 13 C). Optimization of the geometry of 2 with a fixed O···H distance of 2.20 Å reproduced the experimental nonplanarity of the molecule [18,21] and subsequent calculation of the NMR chemical shifts gave much better agreement with the experimental values (δ = 9.48 ppm instead 10.38 ppm in comparison to the experimental value of 9.69 ppm, Table 1). It was concluded that the partially optimized geometry of bindone is very close to the real geometry in solution.…”

Section: Intramolecular Aromatic C-h···o Bonding In 2a-4amentioning

confidence: 50%

“…Both ab initio and DFT geometry optimizations provide generally good agreement with the experimental values, although the hydrogen bonding strength is overestimated. Thus, for bindone 2 the optimized O···H distances (2.02-2.07 Å depending on the calculation method [18] ) were shorter than the experimental value of 2.18 Å; [21] consequently, the calculated [B3LYP/6-31G(2d,2p)] chemical shifts of the bonded hydrogen atom were by 0.8-1.2 ppm larger than the experimental value of 9.69 ppm as a result of the more pronounced influence of the carbonyl carbon atom. The other calculated chemical shifts were in excellent agreement with the experimental values (deviations within 0.1-0.2 ppm for 1 H and 2-3 ppm for 13 C).…”

Section: Intramolecular Aromatic C-h···o Bonding In 2a-4amentioning

confidence: 93%

Inter‐ and Intramolecular C–H···O Bonding in the Anions of 1,3‐Indandione Derivatives

Sigalov¹,

Krief²,

Shapiro³

et al. 2008

Eur J Org Chem

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Derivatives of a series of 1,3-indandione (1) self-condensation products (2-4) and their anions (2a-4a) were investigated by NMR and UV/Vis spectroscopy and quantum mechanical calculations. These compounds exhibit a number of unusual features in their NMR spectra. Parent compound 1 is nearly not ionized in DMSO, whereas 3 is ionized completely. In contrast, derivatives 2 and 4 undergo partial ionization in DMSO and interaction between the neutral and anionic species affords the anionic intermolecular complexes, which exhibit both temperature-and concentration-dependent NMR spectra. The NMR spectra of pure salts 2a and 3a

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“…A similarity between the cell constants and symmetry of the racemate [a = 11.407, b = 18.005, c = 7.177 A, fl=95.30 °, V= 1468.3, P21/n, Bravic, Gaultier & Hauw, (1971)] and the (-) isomer was noticed. Another example in which optical isomers and racemates are isostructural occurs in amino acids exhibiting some dominant packing feature (Benedetti, Pedone & Sirigu, 1973 ;Di Blasio, Pedone & Sirigu, 1975) and it was therefore decided to attempt to solve the (-) structure with the racemate as a starting point.…”

mentioning

confidence: 78%