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1.
Naoya Morohashi Kohei Ebata Tetsutaro Hattori 《Journal of inclusion phenomena and macrocyclic chemistry》2018,90(3-4):279-285
Upon stirring inclusion crystals of p-tert-butylthiacalix[4]arene (2) in solvents with heating, guest compounds were efficiently desorbed to yield guest-free crystals. More specifically, upon treatment with methanol, the exchange of guest compounds with methanol in the crystals, followed by the desorption of the methanol afforded metastable host crystals 2β, whereas, upon treatment with heptane, the dissolution of the inclusion crystals and simultaneous crystallization of compound 2 afforded stable host crystals 2α. Further, a host crystal of p-tert-butylcalix[4]arene (1) was recovered by the treatment of 2:1 (host/guest) inclusion crystals of compound 1 with supercritical carbon dioxide (scCO2), and through the combination of the guest exchange of 1:1 inclusion crystals of compound 1 with hexane and scCO2 treatment of the resulting 2:1 inclusion crystals 12·hexane. Although the recovered host crystal of compound 1 contained a small amount of CO2, it could be reused for the inclusion of organic compounds. 相似文献
2.
The reaction of acryloyl chloride with the monoamine derivative of p-tert-butylthiacalix[4]arene was used to synthesize p-tert-butylthiacalix[4]arene monoacrylamide in the 1,3-alternate conformation. The effect of the nature of the amine on the result of its Michael reaction with the synthesized p-tert-butylthiacalix[4]arene monoacrylamide was studied. The latter was reacted with piperazine to obtain bisthiacalix[4]arene with the macrocyclic fragments in the 1,3-alternate conformation. 相似文献
3.
Mono-, di-, and tetrasubstituted derivatives of p-tert-butylthiacalix[4]arene containing tert-butylcarbamate, tert-butylcarbonate, and tert-butyl fragments have been prepared for the first time. Depending on the reaction conditions (reagents ratio, temperature, and the presence of a base), the interaction of the monoamine derivative of p-tert-butylthiacalix[4]arene with di-tert-butyl dicarbonate can lead to the formation of mono-, di-, and tetrasubstituted products. 相似文献
4.
D. V. Steglenko I. S. Ryzhkina A. I. Konovalov A. G. Starikov V. I. Minkin 《Russian Chemical Bulletin》2016,65(1):47-53
The self-assembly of tetrathiacalix[4]arene and tetraoxacalix[4]arene molecules functionalized by hydrazide groups was studied by DFT calculations at B3LYP/6-31G(d,p) level. The calculations were performed for the cone and 1,3-alternate conformations. The associates of calix[4]arenes in the cone conformation are stabilized by multiple hydrogen bonds with inclusion of all hydrazide groups in the formation of the globule, which suppresses the formation of extended structures. 相似文献
5.
Bosco Christin Maria Arputham Ashwin Ramesh Kumar Chitumalla Arulanandu Herculin Arun Baby Joonkyung Jang Paulpandian Muthu Mareeswaran 《Journal of inclusion phenomena and macrocyclic chemistry》2018,90(1-2):51-60
The supramolecular host–guest investigation of Coumarin 460 (C460), a salient coumarin family dye molecule is studied with a noteworthy host molecule, p-sulfonatocalix[4]arene (p-SC4). The investigation is carried out by both experimental and theoretical approach. The binding affinity of C460 with p-SC4 is experimentally studied using absorption, emission, excited state lifetime and Cyclic Voltammetry methods. The binding constant is around 103 M??1, which shows potent binding. The binding stoichiometry is 1:1. The binding orientations and binding energies are studied using computational simulations. The mode of binding is also established using NMR spectral techniques. 相似文献
6.
E. V. Khomich M. N. Kashapov I. M. Vatsuro E. A. Shokova B. B. Kovalev 《Russian Journal of Organic Chemistry》2007,43(2):192-200
Asymmetric p-tert-butylcalix[4]-p-R-thiacalix[4]arene tubes (R = tert-Bu, H, 1-adamantyl) were prepared for the first time by reaction of tosyloxyethoxy derivative of p-tert-butylcalix-[4]arene and the corresponding p-R-thiacalix[4]arenas in acetonitrile in the presence of K2CO3. Complex formation of compounds obtained with sodium, potassium, and rubidium iodides in CDCl3-CD3OD, 4:1, was studied by means of 1H NMR. The ionophore properties of the molecule were governed by the character of substituents on the upper rim of the thiacalixarene fragment, and only the molecular tube containing a fragment of the p-(1-adamantyl)-thiacalix[4]arene quantitatively bound potassium ions (quickly) and rubidium ions (slowly). 相似文献
7.
R. V. Ziatdinova N. A. Losev I. S. Teren’tev A. V. Gerasimov L. S. Yakimova V. G. Evtyugin I. I. Stoikov 《Russian Journal of General Chemistry》2017,87(9):1969-1976
Three stereoisomers (cone, partial cone, and 1,3-alternate) of p-tert-butylthiacalix[4]arene bearing four anchor propyltriethoxysilane substituents at the lower rim were synthesized for the first time. Surface modification of silica nanoparticles (d = 12 nm) with the synthesized macrocycles gave novel hybride thiacalix [4]arene?SiO2 particles. The obtained nanostructured adsorbents were found to efficiently extract nitroaromatic compounds from aqueous solutions. The partial cone and 1,3-alternate thiacalix[4]arene–SiO2 hybrid particles showed affinity to nitrophenols. 相似文献
8.
K. S. Shibaeva A. A. Nazarova D. I. Kuznetsova I. I. Stoikov 《Russian Journal of General Chemistry》2016,86(3):579-583
Aminobismethylenephosphonic acids on a platform of p-tert-butylthiacalix[4]arene were obtained by reacting macrocyclic amines with phosphorous acid and formaldehyde under acid catalysis. Free phenol hydroxy groups on the lower rim of p-tert-butylthiacalix[4]arene were found to inhibit the interaction with the amino moieties of the macrocycle. In the case of amino derivatives of thiacalix[4]arene containing no hydroxy groups the reaction led to the formation of target compounds in good yields. 相似文献
9.
I. V. Smirnov E. S. Stepanova N. M. Ivenskaya M. D. Karavan S. R. Zaripov S. E. Solovieva I. S. Antipin 《Doklady Chemistry》2018,479(1):36-40
Trends of cesium-137 and americium-241 extraction from carbonate–alkaline media with p-tert-butylcalix[n]arenes with macrocycles of different size (n = 4, 6, 8), including monofunctional derivatives with lipophilic substituents for increasing their solubility in organic media, were studied. It was demonstrated that O-n-octyl ethers of p-tert-butylcalix[6]arene appeared to be the most efficient extractants for Cs(I) cations, while it was p-tert-butylthiacalix[4]arene for and americium(III) cations. 相似文献
10.
S. E. Solov’eva A. O. Omran M. Gruener W. D. Habicher I. S. Antipin A. I. Konovalov 《Journal of Structural Chemistry》2005,46(1):S16-S21
Template effect of alkali metal ions was employed to prepare three isomers of tetraamide of p-tert-butylthiacalix[4]arene: cone, partial cone and 1,3-alternate. It was demonstrated that pre-organization of four amide fragments attached to the calix[4]arene platform has a strong macrocyclic cooperative effect on the extraction ability of the title hosts. 相似文献
11.
Hui Ren Benjamin Ourri Erwann Jeanneau Tao Tu Isabelle Bonnamour Ulrich Darbost 《Transition Metal Chemistry》2016,41(8):827-834
A series of calix[4]arene supported N-heterocyclic carbene palladium complexes were successfully prepared and characterised. Their X-ray crystal structures were obtained and are discussed. Notably, the dimeric compound b[5-(3-N-4,5-diphenylimidazol-2-yliden-1-yl)-25,26,27,28-tetrapropyloxy calix[4]arene] palladium(II) dibromide (cone) showed pseudo-polymorphism. 相似文献
12.
Natalie Kahwajy Alireza Nematollahi Ryung Rae Kim W. Bret Church Nial J. Wheate 《Journal of inclusion phenomena and macrocyclic chemistry》2017,87(3-4):251-258
The potential anticancer drug phenanthriplatin, [cis-(NH3)2(phenanthridine)Cl]+, forms supramolecular complexes with cucurbit[n]urils (CB[n], n?=?7 or 8), β-cyclodextrin and para-sulfonatocalix[4]arene (sCX[4]) as determined by 1H NMR spectroscopy and molecular modeling. The results show that cucurbit[7]uril binds over the long arm of the drug, where hydrophobic effects and two hydrogen bonds stabilise binding. For cucurbit[8]uril, two phenanthriplatin molecules can bind simultaneously within the macrocycle’s cavity. Unfortunately, Na+ was able to displace the drug from both CB[7] and CB[8] making the macrocycles unsuitable as delivery vehicles for phenanthriplatin. Drug binding to β-cyclodextrin occurs at the portal of the macrocycle with no part of the phenanthriplatin located within the cavity. Phenanthriplatin binding to sCX[4] occurs in a 2-to-1, macrocycle-to-drug, ratio with the formation of a capsule-like complex where each sCX[4] binds over opposing ends of the drug. The results indicate that para-sulfonatocalix[4]arene is the only suitable macrocycle of the four studied for further research into phenanthriplatin drug delivery. 相似文献
13.
V. V. Kovalev E. V. Khomich E. A. Shokova V. A. Babain M. Yu. Alyapyshev 《Russian Journal of General Chemistry》2008,78(1):19-25
Synergistic extraction of long-lived fission products 137Cs+, 85Sr2+, and 152Eu3+ from dilute HNO3 into dichloroethane with ligands derived from p-(1-adamantyl)thiacalix[4]arene in mixtures with chlorinated cobalt dicarbollide was studied. An extraordinary synergistic effect is observed in extraction of europium with p-(1-adamantyl)thiacalix[4]arene tetraacetate derivative. Amides of p-(1-adamantyl)thiacalix-[4]arene tetracarboxylic acid are selective toward europium, although their extraction ability toward the examined ions is lower than that of the classical extractant, p-(1-adamantyl)calix[4]arene tetracarboxylic acid diethylamide. 相似文献
14.
Effect of copper(I) on the conformation of the thiacalixarene platform in azide-alkyne cycloaddition
V. A. Burilov R. R. Ibragimova R. I. Nugmanov R. R. Sitdikov D. R. Islamov O. N. Kataeva S. E. Solov’eva I. S. Antipin 《Russian Chemical Bulletin》2015,64(9):2114-2124
New lower-rim tetrasubstituted p-tert-butylthiacalix[4]arene derivatives bearing alkyl, propargyl, or triazole-containing substituents were synthesized. The structures of these compounds were determined by 1D and 2D NMR spectroscopy in solution and by X-ray diffraction in the solid phase. The copper-catalyzed azide-alkyne cycloaddition (CuAAC) of azides to a mixture of 1,3-alternate–partial cone stereoisomers of dipropargyl derivatives of thiacalix[4]arene affords triazole-containing products exclusively in the 1,3-alternate conformation. 相似文献
15.
Mahesh Kalidasan S. Sangilipandi R. Nagarajaprakash K. Mohan Rao 《Transition Metal Chemistry》2016,41(3):261-270
The reactions of [(arene)RuCl2]2 (arene = p-cymene or benzene) and [Cp*MCl2]2 (M = Rh or Ir) with N,N′-bidentate chelating ligands 2-[3-(2-pyridyl)pyrazolyl]pyrimidine (L1) and 4-phenyl-(2-pyridyl)thiazole (L2) leads to the formation of mononuclear complexes of general formula [(arene)/Cp*M(L)Cl]PF6. Eight such complexes have been prepared and characterized by spectroscopic techniques. In addition, five of the complexes were also characterized by single-crystal X-ray diffraction. These complexes have typical piano-stool geometries around the metal center, with five-membered metellacycles in which L1 and L2 both act as N,N′-chelating ligands. Moreover, L1 prefers to coordinate through its pyrimidine and pyrazolyl nitrogen atoms, rather than the pyridine nitrogen. 相似文献
16.
Benita Barton Eric C. Hosten Pieter L. Pohl 《Journal of inclusion phenomena and macrocyclic chemistry》2018,92(3-4):329-337
In this work, we reveal that the compound (?)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) is a highly efficient host material for nitroaromatics o-nitrotoluene (o-NT), m-nitrotoluene (m-NT), p-nitrotoluene (p-NT) and nitrobenzene (NB). Each of these guests was included with a 2:1 host:guest ratio. The host displayed selectivity for p-NT and NB when these guests were mixed in equimolar proportions with any one of the other guest solvents, and the host recrystallized from this binary mixture. A selectivity order for the host in these conditions was thus noted to be NB?≈?p-NT?>?o-NT?>?m-NT. Furthermore, guests were also mixed in non-equimolar proportions and the host behaviour analysed, the results of which were in accordance with observations from the equimolar studies. Additionally, an equimolar quaternary experiment of all four guests provided a somewhat adjusted host selectivity order [p-NT (39.9%)?>?NB (30.2%)?>?m-NT (17.1%)?>?o-NT (12.8%)]. Single crystal diffraction analyses of all four complexes showed the crystals to share the same host packing, and comparable host–guest interactions were observed in each. However, thermal analyses, both DSC and TG, showed that the preferred guests p-NT and NB formed complexes with increased relative thermal stabilities, and this observation correlated with the selective behaviour of the host in competition experiments. 相似文献
17.
L. N. Mazalov N. A. Kryuchkova E. A. Korotaev A. D. Fedorenko V. G. Torgov G. A. Kostin V. I. Kalchenko 《Journal of Structural Chemistry》2011,52(1):36-44
The X-ray photoelectron and X-ray emission spectra as well as the charge state of thiacalix[4]arenes in the cone and 1,3-alternate conformations and calix[4]arene thioesters were studied. The donor ability of sulfur bridging atoms in the studied compounds was shown to be close to that in dialkyl sulfides. The internal X-ray transitions (K α and K β) were described by the energy of Kohn-Sham orbitals calculated by DFT method with relaxation corrections. 相似文献
18.
N. G. Kozlov Yu. D. Zhikharko L. I. Basalaeva 《Russian Journal of Organic Chemistry》2018,54(10):1493-1497
A series of new 11-(R-phenyl)-8,9-dihydro-7H-benzo[f]cyclopenta[b]quinolin-10(11H)-ones and 7,14-bis(R-phenyl)-2,3,9,10,11,14-hexahydrocyclopenta[2,3]quinolino[8,7-h]cyclopenta[b]quinoline-1,8(4H,7H)-diones were synthesized by three-component condensation of naphthalen-2-amine or naphthalene- 1,5-diamine with substituted benzaldehydes and cyclopentane-1,3-dione in one step through intermediate formation of unstable arylaminoketoenol. 相似文献
19.
Joanna Dziemidowicz Dariusz Witt Janusz Rachoń 《Journal of inclusion phenomena and macrocyclic chemistry》2008,61(3-4):381-391
Series of the calix[4]arene phosphonic acids with various substituents at the lower rim was synthesized. Complexing properties of these receptors towards methyl esters of six amino acids strongly depended on the calix[4]arene conformation flexibility. The complex formation processes were monitored using 1H NMR spectroscopy (deuterated phosphate buffer at pD 7.3, 22 °C) and association constant values were evaluated. Inherently mobile calix[4]arene molecule 3 occurred in cone conformation in aqueous solution turned out to be more effective in complexation of the basic amino acids methyl esters compared to the rigid 2 and flexible 4. Mixed 1:2 and 2:1 (host–guest) complexes were observed for compound 1 with all amino acids methyl esters. 相似文献
20.
G. N. Chekhova Yu. V. Shubin D. V. Pinakov N. I. Alferova 《Russian Journal of Physical Chemistry A, Focus on Chemistry》2008,82(7):1061-1065
Phase equilibria in the thiourea (host)-bromoform (guest) binary system were studied by physicochemical analysis methods over the temperature range 270–455 K. The stoichiometry and stability region were determined for the channel-type compound CHBr3 · 2.40(2)(NH2)2CS; the compound was observed for the first time. When heated, the clathrate incongruently decomposed at 424.0 ± 0.8 K to rhombic thiourea and the guest component. The solubility isotherm of the thiourea-bromoform-acetic acid system was studied to find that the compound was thermodynamically stable at 293 K over the range of guest component concentrations 100–35 wt %. A decrease in its content in an equilibrium mother liquor resulted in the appearance of X-ray diffraction reflections of the initial host α polymorph. Rhombohedral cell parameters were determined (space group R-3c, a = 15.89(1) Å, c = 12.40(1) Å, V = 2711(6) Å3, d calcd = 2.000 g/cm3, and d expt = 1.98(2) g/cm3). The mode of packing of bromoform molecules was compared with the organization of the guest subsystem in inclusion compounds formed by the substances studied. 相似文献