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Isoniazid cocrystallisation with dicarboxylic acids: vapochemical, mechanochemical and thermal methods
2016
Cocrystallisation with a series of related compounds allows for the exploration of trends and limitations set by structural differences between these compounds. In this work, we investigate how the length of a dicarboxylic acid influences the outcome of cocrystallisation with isoniazid. We have performed a systematic study on the mechanochemical, thermal and solvent vapour-assisted cocrystallisation of aliphatic dicarboxylic acids (C3–C10) with isoniazid. Our results demonstrate that the rate of mechanochemical and vapour-assisted cocrystallisation depends on the acid chain length and shows alternation between odd- and even-chain acids. The results of thermal cocrystallisation showed that t…
Highly Diastereoselective Arylation of (S)-Mandelic Acid Enolate: Enantioselective Synthesis of Substituted (R)-3-Hydroxy-3-phenyloxindoles and (R)-B…
2005
An easy access to substituted (R)-3-hydroxy-3-phenyloxindoles, (R)-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2S,5S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several o- and p-halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the o-nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure (R)-3-hydroxy-3-phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all t…
Electrochemical carboxylation of aldehydes and ketones with sacrificial aluminum anodes.
1986
Abstract The electrocarboxylation of aldehydes to the corresponding α-hydroxyacids was described as impossible with conventional electrochemical systems. It is reported here that it is possible to realize it in diaphragmless cells making of sacrificial aluminum anodes. The method can be used also for the electrocarboxylation of ketones with good yields.
Influence of the nature of the substrate and of operative parameters in the electrocarboxylation of halogenated acetophenones and benzophenones
2005
Abstract The electrocarboxylation of halogenated acetophenones and benzophenones to the corresponding hydroxycarboxylic acids has been carried out in undivided cell equipped with aluminium sacrificial anode and using 1-methyl-2-pyrrolidinone (NMP) as the solvent. The radical anion generated by the electro-reduction of the aromatic ketone is involved in several competitive reactions which lead to the formation of the target hydroxycarboxylic acid, the corresponding alcohol and pinacol and the de-halogenated parent ketone. If sufficiently negative working potentials are imposed, the latter is reduced to the corresponding carboxylate, pinacol and alcohol. Very different results in terms of sel…
A series of lanthanide(iii) metal-organic frameworks derived from a pyridyl-dicarboxylate ligand: single-molecule magnet behaviour and luminescence p…
2020
The reactions of LnIII ions with a versatile pyridyl-decorated dicarboxylic acid ligand lead to the formation of a series of novel three-dimensional (3D) Ln-MOFs, [Ln3(pta)4(Hpta)(H2O)]·xH2O (Ln = Dy (1), Eu (2), Gd (3), Tb (4), H2pta = 2-(4-pyridyl)-terephthalic acid, x = 6 for 1, 2.5 for 2, 1.5 for 3 and 2 for 4). The Ln3+ ions act as nine-coordinated muffin spheres, linking to each other to generate trinuclear {Ln3(OOC)6N2} SBUs, which are further extended to be interesting 3D topological architectures. To the best of our knowledge, the Dy-MOF exhibits zero-field single-molecule magnet (SMM) behaviour with the largest effective energy barrier among the previously reported 3D MOF-based Dy…
Synthesis, characterization, cytotoxic activity and crystal structures of tri- and di-organotin(IV) complexes constructed from the β-{[(E)-1-(2-hydro…
2006
Abstract Reactions of potassium β-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}propionates (L1HK-L3HK) and potassium β-{[(2Z)-(3-hydroxy-1-methyl-2- butenylidene)]amino}propionate (L4HK) with R3SnCl (R = Ph and nBu) and nBu2SnCl2 yielded complexes of composition Ph3SnL1H (1), Ph3SnL2H (2), Ph3SnL4H (3), nBu3SnL1H (4), and {[nBu2Sn(L2H)]2O}2 (5) and {[nBu2Sn(L3H)]2O}2 (6), respectively. These complexes have been characterized by 1H, 13C, 119Sn NMR, ESI-MS, IR and 119mSn Mossbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of 1, 4, 5 and 6 were determined. In the solid state, compound 1 is a one-dimensional polymer built from SnPh3 moieties bridged by s…
A bibracchial lariat aza-crown ether as an abiotic catalyst of malonic acid enolization
2007
A bibracchial lariat aza-crown ether (L) consisting of 2-aminoethylnaphthyl moieties appended to a 2 : 2 azapyridinophane structure displays significant activation of H–D exchange in malonic acid. The compound forms very stable adducts with malonate anions (MA) in the 2–10 pH range. Molecular dynamics studies performed for the species resulting from the interaction of the hexaprotonated macrocycle and the dianion show that malonate is encapsulated by L with distances between the CH2 group of malonate and the pyridine nitrogens of ca. 3.5 A. The pendant arms of L cap above and below the anion, defining a pseudo-cage structure. Quantum chemical calculations for α-proton abstraction from malon…
Chiral Molecular Magnets: Synthesis, Structure, and Magnetic Behavior of the Series [M(L-tart)] (M = MnII, FeII, CoII, NiII;L-tart = (2R,3R)-(+)-tart…
2006
A new series of layered magnets with the formula [M(L-tartrate)] (M = Mn(II), Co(II), Fe(II), Ni(II); L-tartrate = (2R,3R)-(+)-tartrate) has been prepared. All of these compounds are isostructural and crystallize in the chiral orthorhombic space group I222, as found by X-ray structure analysis. Their structure consists of a three-dimensional polymeric network in which each metal shows distorted octahedral coordination bound to four L-tartrate ligands, two of which chelate through an alcohol and a carboxylate group and the other two bind terminally through a monodentate carboxylate group. The chirality of the ligand imposes a Delta conformation on all metal centers. Magnetically, the paramag…
The chemistry of death--Adipocere degradation in modern graveyards.
2015
The formation of adipocere slows further decomposition and preserves corpses for decades or even centuries. This resistance to degradation is a serious problem, especially with regard to the reuse of graves after regular resting times. We present results from an exhumation series in modern graveyards where coffins from water-saturated earth graves contained adipocere embedded in black humic material after resting times of about 30 years. Based on the assumption that this humic material resulted from in situ degradation of adipocere, its presence contradicts the commonly held opinion that adipocere decomposition only occurs under aerobic conditions. To test our hypothesis, we collected black…
Effect of carboxymethyl cellulose concentration on rheological behavior of milk and aqueous systems. A creep and recovery study
2009
Carboxymethyl cellulose (CMC) is an anionic polysaccharide used mainly as stabilizer and thickener agent. The purpose of this study was to investigate the effect of CMC concentration on viscoelasticity of dairy and aqueous model systems through the analysis of creep and recovery tests. The viscoelastic properties of different concentrations of CMC (0.75, 1.00, 1.25, and 1.50% w/w) in two milk systems (skimmed milk and whole milk) were compared with those of the same concentration of biopolymer in aqueous solution. Creep curves were fitted to a six parameter mechanical model (Burger + Kelvin-Voigt), whereas an empirical equation was used for recovery. The creep and recovery properties of sam…