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1.
S. E. Solovieva S. R. Kleshnina M. N. Kozlova L. F. Galiullina A. T. Gubaidullin Sh. K. Latypov I. S. Antipin A. I. Konovalov 《Russian Chemical Bulletin》2008,57(7):1477-1485
Stereoisomers of thiacalix[4]arenes unsubstituted at the upper rim and containing four carbonyl fragments have been synthesized
for the first time. Their structures were studied by 1D and 2D NMR spectroscopy, IR spectroscopy, and mass spectrometry. The
complexation properties of the macro-cycles toward alkaline metal cations were estimated by the picrate extraction method.
The absence of the preorganization effect in the case of the thiacalixarenes unsubstituted at the upper rim is the main reason
for the sharp decrease in their extraction ability.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1448–1456, July, 2008. 相似文献
2.
Ivan I. StoikovOmran A. Omran Svetlana E. SolovievaShamil K. Latypov Konstantin M. EnikeevAidar T. Gubaidullin Igor S. Antipin Alexander I. Konovalov 《Tetrahedron》2003,59(9):1469-1476
The three conformations of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[(benzoyl)methoxy]-2,8,14,20-tetrathiacalix[4]arene 1: cone, partial cone and 1,3-alternate, were prepared by the treatment of 5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiacalix[4]arene-25,26,27,28-tetraol (TCA) with α-bromo acetophenone in the presence of appropriate alkali carbonate M2CO3 (M=Na, K, Cs) as base catalyst in acetonitrile. Structure of the conformers were established by 1H NMR, 1H-1H COSY, 1D NOE, 2D ROESY and X-ray experiments. The alkali cation binding selectivity of the obtained macrocycles was investigated by the ion-pair extraction method. 相似文献
3.
Sami Ben Maamar Natsagma Jadambaa Francis Vocanson Faouzi Meganem Isabelle Dumazet-Bonnamour 《Supramolecular chemistry》2013,25(6):450-454
New thiacalix[4]arenes appended with three amide functions have been prepared. Their conformations have been solved thanks to 1H NMR 2D correlation spectroscopy (COSY) and nuclear overhauser and exchange spectroscopy (NOESY). The complexation ability of these ligands towards various metal ions (Cd2 + , Pb2 + , Pd2 + , Ni2 + , Hg2 + , Hg+, Ag+, Zn2 + and Cu2 + ) has been investigated by the UV–vis absorption and the stoichiometry of the metal–ligand complexes was determined. 相似文献
4.
Manabu Yamada Muniyappan Rajiv Gandhi Yoshihiko Kondo Fumio Hamada 《Supramolecular chemistry》2014,26(7-8):620-630
The ability of chloroform solutions of p-diethylaminomethylthiacalix[4]arene 1 to extract platinum from HCl media was tested. As an ion-pair extractant, compound 1 had the highest platinum extraction ability among all the thiacalix[n]arene derivatives tested in this study. Compound 1 was a highly specific extractant for Pt(IV) ions from single-metal solutions and platinum-group metal solutions from automotive catalyst residue. Various conditions such as contact time, pH, concentration of 1, effect of chloride ions, effect of acidity and Pt(IV) concentration were studied. The distribution ratio of platinum ions (D) was calculated. The platinum complex stoichiometry ratio was obtained using slope analysis. The 1–Pt(IV) complex was characterised using X-ray photoelectron spectroscopy, FT-IR and 1H NMR. Finally, the Pt(IV) extraction percentage of compound 1 was compared with that of previously reported thiacalix[n]arene-based extractants. 相似文献
5.
Hasalettin Deligöz 《Journal of inclusion phenomena and macrocyclic chemistry》2001,39(1-2):123-125
Two compounds (1 and 2) which have calix[4]arene units and their Na+ and K+-complexes were prepared. All the complexes have a metal-ligand ratio of 1 : 1. The newly prepared compounds were characterized on the basis of their 1H NMR, IR, UV-visible as well as elemental analysis. 相似文献
6.
High level DFT was applied to study structure and conformational equilibrium of amino and mercaptocalix[4]arenes possessing methylene groups or sulfur atoms at their four junctions. All the calculations point to cone and 1,3-alternate as the most stable conformers for sulfur and methylene bridged compounds, respectively. The presence of four sulfur atoms in place of the methylene bridges can lead to novel features in the complexation with transition metals. The host–guest 1:1 complexes between Zn2+ and each conformer of tetraaminothiacalix[4]arene were also investigated at the same DFT level. The four nitrogens of amino groups play a dominant role in the interaction with Zn2+ via distorted tetrahedral coordination for 1,3-alternate, or distorted square planar for partial cone and 1,2-alternate. On the other hand, the 2:1 complexes with cone show that the sulfur bridges can also bind Zn2+ and contribute to form two sets of five-membered chelated rings with two N donor atoms. 相似文献
7.
Mitesh H. Patel 《Tetrahedron》2008,64(9):2057-2062
New chromogenic supramolecular vanadophiles were designed and synthesized by incorporating hydroxamic acid chains on a 1,3-alternate thiacalix[4]arene scaffold and were found to show high affinity toward vanadate ions. The article describes a comprehensive design process to devise a tailor-made co-ordination cavity for vanadate ions by pre-organization of hydroxamic acid chelating moieties on a 1,3-alternate thiacalix[4]arene scaffold. These receptors simultaneously co-ordinate two vanadate ions giving a highly ‘staggered’ geometry with almost D2d symmetry. Proposed structures and complexation behavior of the receptors were explained by critical examination of FTIR, UV-visible, mass, and 1H NMR data. 相似文献
8.
Natalia Selivanova Aidar Gubaidullin Pavel Padnya Ivan Stoikov Yuriy Galyametdinov 《Liquid crystals》2019,46(3):415-421
Supramolecular organised materials were prepared from nonionic surfactants and the following macrocyclic ionic liquids: n-tert-butylthiacalix[4]arenes containing quaternary ammonium fragments with amino acid substituents. Tetraethylene glycol monododecyl ether and decadiethylene glycol monododecyl ether were used as nonionic surfactants. They form lamellar and hexagonal mesophases in aqueous media, respectively. Liquid crystal and structural properties of these systems were studied. Intermolecular interactions of system components leading to formation of lyomesophases were estimated. Molecular structure of thiacalixarene contributes to the formation of a hydrogen bonding with surfactants. This process, in turn, initiates formation of a denser packed hexagonal structure. 相似文献
9.
Structure and conformational equilibrium of thiacalix[4]arene by density functional theory 总被引:2,自引:0,他引:2
Density functional theory calculations for the structure and conformational equilibrium of thiacalix[4]arene are reported. The conformational equilibrium of thiacalix[4]arene, a heterocalixarene in which the phenol groups are bridged by sulphur atoms is compared to the conformational equilibrium of calix[4]arene. Thiacalix[4]arene conformational energies relative to the cone conformer (ΔE's) are reduced in comparison with calix[4]arene. This conformational change is in qualitative agreement with recent NMR spectroscopy measurements of the conformational equilibrium for a tetraethylether of thiacalix[4]arene in a CDCl3 solution which indicates an enhanced chemical exchange of thiacalixarene conformers in comparison with similar methylene bridged structures. Density functional theory results for the structure of thiacalix[4]arene are in good agreement with recent X-ray diffraction measurements. The electrostatic potentials in the cone conformers of thiacalix[4]arene and calix[4]arene suggest that their complexation or recognition abilities can be significantly different. Dipole moments of the four thiacalix[4]arene conformers are in the order: cone>1,2-alternate>partial-cone>1,3-alternate. 相似文献
10.
Kovalenko V. I. Chernova A. V. Borisoglebskaya E. I. Katsyuba S. A. Zverev V. V. Shagidullin R. R. Antipin I. S. Solov"eva S. E. Stoikov I. I. Konovalov A. I. 《Russian Chemical Bulletin》2002,51(5):825-827
The joint FTIR spectroscopic study and ab initio quantum-chemical calculations (HF/3-21G and PBE/TZ2P methods) showed that thiocalix[4] arene molecules adopt the cone conformation in CCl4 solutions. The weakening of the cooperative intramolecular H bond in thiocalix[4]arenes compared to the corresponding calix[4]arenes can be due to the larger thiocalixarene macrocycle, bifurcated hydrogen bond in it, and electron density transfer from the bridging S atom to the benzene ring. 相似文献
11.
Tomáš Landovský Markéta Tichotová Lukáš Vrzal Jan Budka Václav Eigner Hana Dvořáková Pavel Lhoták 《Tetrahedron》2018,74(8):902-907
Phenoxathiin-based thiacalix[4]arene, obtained by the acid-catalysed rearrangement of the corresponding spirodienone derivative, was immobilized using the alkylation with chloroacetonitrile to yield three (out of four theoretically possible) stereoisomers. As the conformational outcome of the reaction could not be unambiguously assigned using standard NMR techniques, the method of Residual Dipolar Coupling constants (RDCs) was applied. The measuring of an anisotropic through-space dipole-dipole interactions in the lyotropic liquid crystalline alignment medium (PELG, poly-γ-ethyl-l-glutamate, and PBLG, poly-γ-benzyl-l-glutamate) enabled the assignment of the individual conformers. The usefulness of this approach was finally confirmed by the X-ray crystallography data. 相似文献
12.
Zouhair Asfari Jean-Pierre Astier Christophe Bressot Jacques Estienne Gerard Pepe Jacques Vicens 《Journal of inclusion phenomena and macrocyclic chemistry》1994,19(1-4):291-300
1,2-bis-crown-5-calix[4]arene (3) was prepared by reacting calix[4]arene (1) with tetraethylene glycol di-p-toluenesulphonate (2) in the presence of cesium carbonate in 9% yield. The X-ray structure of (3) was determined. Crystal data for C44H52O10 are as follows: monoclinic, space groupP
2/c
witha=18.006(8) Å,b=10.680(4) Å,c=22.359(6) Å, =112.93(3)°,V=3958(6) Å3,Z=4,D
calc=1.2 g cm–3, the finalR value is 0.11 for the 1851 observed reflections (I>3(I)). The single crystal included two similar but slightly different molecules immobilized in a pinched-cone conformation withC
2 symmetry. The two enantiomorphous molecules were analyzed by molecular mechanics using the GenMol program to model the selective alkali-metal complexation.This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes. 相似文献
13.
S. Taghvaei-Ganjali 《Supramolecular chemistry》2013,25(5):527-530
A new Dimeric calixarene from the head to head linkage of two calix[4]arene units fixed in the cone conformation was synthesized via Sonogashira cross-coupling reaction. The structure of 10 was confirmed by NMR, MS and IR-spectroscopy. 相似文献
14.
Using a click reaction between alkynylthiacalix[4]arene and ethyl 2-azidoacetate followed by an ammonolysis with ethanolamine,leucinol and hydrazine hydrate,respectively,three novel thiacalix [4]arene derivatives 4,5 and 6 with triazolyl and hydrogen bonding groups(NH and OH) were synthesized in high yields.They exhibited excellent extraction capability for six anionic and cationic dyes.The flexible cavity,π-triazole rings and hydrogen bonding groups all play crucial roles in dye complexation. 相似文献
15.
A series of conformationally diverse novel tetrathiacalix[4]arene(amido)crowns and amides from tetrakis((ethoxycarbonyl)methoxy)p-tert-butyl tetrathiacalix[4]arene and its debutylated analog have been prepared by their reaction with diamines [H2N(CH2)nNH2; n=2,3,4, and 6] and polyamines. It has been determined that the length of the alkyl spacer in diamines is pivotal for the formation of either the tetrathiacalix[4]arene bis(amido)crowns or tetrathiacalix[4]arene amides with pendant amine functions. The synthesized compounds represent potential building blocks for achieving sophisticated molecular assemblies for molecular organization and recognition. Single crystal X-ray analysis of tetrathiacalix[4]arene bis(amido)crown 6a revealed that it has a 1,3-alternate conformation, which forms supramolecular complexes with chloroform. 相似文献
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18.
Alexandre Mathieu Zouhair Asfari Jacques Vicens Pierre Thuéry Martine Nierlich 《Journal of inclusion phenomena and macrocyclic chemistry》2002,43(1-2):133-135
The reaction of p-tert-butyl calix[4]arene 1 with,'-dibromo-o-xylene in basic conditions leads totwo new compounds. One of them is a bis-calix[4]arene, whose crystal structure has been determined. 相似文献
19.
Fa Fu YANG Xia ZHAO Cui Yu HUANG Hong Yu GUO Si Ning ZHENG Qi PENG 《中国化学快报》2006,17(8):1029-1032
Biscalixarenes, as examples of higher order molecular architectures than normal calixarene derivatives, were studied extensively in the recent years due to they possess two calixarene cavities which have the potential for complexing with two guests in two… 相似文献
20.
I. I. Stoikov D. Sh. Ibragimova I. S. Antipin A. I. Konovalov T. A. Gadiev B. I. Khairutdinov F. Kh. Karataeva V. V. Klochkov 《Russian Chemical Bulletin》2004,53(10):2269-2275
New derivatives of p-tert-butylthiacalix[4]arene were synthesized. The conformation of the macrocycles and interproton distances in the synthesized thiacalix[4]arenes in solutions were determined by NMR spectroscopy. p-tert-Butylthiacalix[4]arene distally disubstituted at the lower rim adopts the cone conformation, and the tetrasubstituted products are formed in the 1,3-alternate conformation.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2172–2178, October, 2004. 相似文献