Three novel mono-functionalized arylimido derivatives of hexamolybdate bearing the strongest electron-withdrawing nitro group, (Bu(4)N)(2)[Mo(6)O(18)([triple bond]NAr)] (1, 2 and 3), have been synthesized for the first time by an improved reaction of octamolybdate ion and 3-nitroaniline hydrochloride, 2-methyl-4-nitroaniline hydrochloride and 2-methyl-5-nitroaniline hydrochloride respectively with DCC (N,N'-dicyclohexylcarbodiimide) as a dehydrating agent. Complete assignments were achieved for the title compounds by elemental analysis, IR, (1)H NMR, UV/visible and single-crystal X-ray diffraction analyses. The preliminary antitumor activity test indicated that the title compounds have some effects on the cellular growth inhibition of K562 cells.
Four novel fluoro-functionalized arylimido-substituted hexamolybadates, (n-Bu4N)2[Mo6O18(NAr)] (Ar = 2-CH3-4-FC6H3 (1), 3-CH3-4-FC6H3 (2), 4-FC6H4 (3), or 2-FC6H4 (4)), in which fluorinated phenylimido group linked to an Mo of hexamolybdate by a Mo−N triple bond, have been prepared via the DCC (N,N′-dicyclohexylcarbodiimide) dehydrating protocol of the reaction of α-octamolybdate ion with 2-methyl-4-fluoroaniline hydrochloride, 3-methyl-4-fluoroaniline hydrochloride, 4-fluoroaniline hydrochloride, or 2-fluoroaniline hydrochloride in anhydrous acetonitrile. All these compounds have been characterized by elemental analysis, UV−vis, IR, 1H NMR, and single-crystal X-ray diffraction analyses. The preliminary biological activity test indicated that these compounds display potent herbicidal activity, in particular against the roots of some tested plants (such as Brassica campestris L., Eclipta prostrata L., Echinochloa crusgallis L., and Cirsium japonicum DC.).
Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.005 Å R factor = 0.055 wR factor = 0.161 Data-to-parameter ratio = 12.7For details of how these key indicators were automatically derived from the article, see
Silicon compounds 1b–3b are sila‐analogues of the galbanum odorants α‐galbanone (1a), α‐spirogalbanone (2a), and nor‐α‐galbanone (3a), respectively. Sila‐α‐galbanone (1b), sila‐α‐spirogalbanone (2b), and sila‐nor‐α‐galbanone (3b) were synthesized in multistep syntheses in isomerically pure form, starting from Me2SiCl2, (CH2=CH)2SiCl2, and Me2(CH2=CH)SiCl, respectively. Hydroformylation of vinylsilanes, followed by either ring‐closing aldol condensation or ring‐closing alkene metathesis, were the key steps in these syntheses. The C/Si pairs 1a/1b, 2a/2b, and 3a/3b were studied for their olfactory properties. All compounds possess green‐fruity galbanum‐type odors with pineapple aspects and thus are olfactorily related. However, sila‐analogues 1b–3b were found to be weaker than the corresponding parent carbon compounds 1a–3a. This effect is most pronounced for the C/Si pair 2a/2b as indicated by the odor thresholds of 0.023 ng L–1 air (2a) and 3.8 ng L–1 air (2b). However, due to their higher molecular mass, the silicon compounds are less volatile and thus more substantive in functional applications. In contrast to the stable 5‐silacyclohex‐1‐enes 1b and 2b, the 4‐silacyclopent‐1‐ene 3b shows a limited chemical stability. For compound 3a an extremely low odor threshold of 0.0087 ng L–1 air was measured, and the silicon analogue 3b with an odor threshold of 0.085 ng L–1 air is the sila‐odorant with the lowest odor threshold measured so far.
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