The synthesis of two novel neutral receptors and their anion binding properties

2004 ◽  
Vol 82 (3) ◽  
pp. 454-460 ◽  
Author(s):  
Zhen-Ya Zeng ◽  
Yong-Bing He ◽  
Lan-Hua Wei ◽  
Jin-Long Wu ◽  
Yan-Yan Huang ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Color Change ◽  
Anion Recognition ◽  
Association Constants ◽  
Anion Binding ◽  
Binding Properties ◽  
Pale Yellow ◽  
H Nmr

Two new neutral receptors (1 and 2) containing thiourea and amide groups were synthesized by simple steps in good yields. The binding properties of 1 and 2 with anions were examined by UV–vis, fluorescence, and 1H NMR spectroscopy. Receptor 1 had a better AcO–: H2PO4– selectivity in comparison with that for receptor 2. The association constants of 1·AcO–, 2·AcO–, and 2·H2PO4– were higher in comparison with those of other anions (Cl–, Br–, I–, p-NO2PhO–, and p-NO2PhOPO32–). In particular, a clear color change was observed, from pale yellow to red-brown, upon addition of AcO– to the solution of 1 in DMSO. The UV–vis and fluorescence data indicate that a 1:1 stoichiometry complex is formed between compound 1 or 2 and anions through hydrogen-bonding interactions.Key words: neutral receptors, anion recognition, synthesis, hydrogen bonds.

Experimental and Theoretical Evidence of the Bidentate Binding Mode of Dichloroacetamido Groups at the Upper Rim of Calix[4]arene Hydrogen-Bonding Anion Receptors

2004 ◽  
Vol 69 (5) ◽  
pp. 1063-1079 ◽  
Author(s):  
Alessandro Casnati ◽  
Francesca Bonetti ◽  
Francesco Sansone ◽  
Franco Ugozzoli ◽  
Rocco Ungaro
Keyword(s):  
Hydrogen Bonding ◽  
Binding Mode ◽  
Association Constants ◽  
Anion Binding ◽  
Anion Receptors ◽  
Binding Properties ◽  
Carboxylate Anions ◽  
Molecular Modeling Studies ◽  
Theoretical Evidence ◽  
Upper Rim

Calix[4]arenes in the 1,3-alternate conformation (1-3) and bearing activated amide groups at the upper rim have been synthesized and their anion binding properties studied and compared with conformationally mobile (4) or cone (Ib) receptors having the same binding groups. Association constants determined in CDCl3 show a stronger complexation for Y-shaped carboxylate anions and a higher efficiency for receptors (Ib and 3) bearing dichloroacetamido moieties as hydrogen bonding donor groups. Molecular modeling studies performed on the cone derivative (Ib) and its 1,3-alternate isomer (10) and ab initio calculations on 4-methoxyaniline derivatives (11-13) used as simplified models, reveal that the α,α-dichloroacetamido moieties bind anions in a bidentate fashion using both the N-H and the CHCl2 as hydrogen bonding donor groups. This explains the higher efficiency in carboxylate binding found for Ib and 3 that incorporate the dichloroacetamido binding unit in their structures.

scholarly journals Tripodal halogen bonding iodo-azolium receptors for anion recognition

RSC Advances ◽  
2017 ◽  
Vol 7 (19) ◽  
pp. 11253-11258 ◽  
Author(s):  
Sheila Ruiz-Botella ◽  
Pietro Vidossich ◽  
Gregori Ujaque ◽  
Eduardo Peris ◽  
Paul D. Beer
Keyword(s):  
Hydrogen Bonding ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Anion Binding ◽  
Binding Properties

The preparation and anion binding properties of 1,3,5-tri-substituted benzene platform-based tripodal receptors containing halogen bonding (XB) iodo-imidazolium and iodo-triazolium motifs, and hydrogen bonding (HB) analogues are described.

scholarly journals The road to aryl CH⋯anion binding was paved with good intentions: fundamental studies, host design, and historical perspectives in CH hydrogen bonding

2019 ◽  
Vol 55 (36) ◽  
pp. 5195-5206 ◽  
Author(s):  
Lisa M. Eytel ◽  
Hazel A. Fargher ◽  
Michael M. Haley ◽  
Darren W. Johnson
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Anion Recognition ◽  
Anion Binding ◽  
Feature Article ◽  
The Road ◽  
Historical Perspectives

This feature article highlights recent approaches to anion recognition with a focus on aryl CH hydrogen bonds.

Anionenaktivierung, III. Zur Bedeutung von Wasserstoffbrückenbindungen für das reaktive Verhalten von Kronenäthern und Aminopolyäthern / Anionactivation, III. Anionactivation, III1 Concerning the Significance of Hydrogen-Bonding for the Reactivity of Crown Ethers and Aminopolyethers

1976 ◽  
Vol 31 (9) ◽  
pp. 1192-1200 ◽  
Author(s):  
A. El Basyony ◽  
J. Klimes ◽  
A. Knöchel ◽  
J. Oehler ◽  
G. Rudolph
Keyword(s):  
Hydrogen Bonding ◽  
Chemical Shift ◽  
Hydrogen Bonds ◽  
Crown Ethers ◽  
Organic Molecules ◽  
Substitution Reactions ◽  
Macrocyclic Polyethers ◽  
H Nmr ◽  
Acidic Compounds ◽  
Nmr Signals

Adducts of macrocyclic polyethers (crown ethers) and aminopolyethers1,2 having hydrogen bonds with polar organic molecules, especially with CH-acidic compounds, are described. These can be isolated as solids, and are, as a rule, stoichiometrically consistent. The chemical shift of the 1H NMR signals of the adducts of malononitrile with various crown ethers corresponds to the anionic reactivity of potassium complexes of the crown ethers in the course of nucleophilic substitution reactions.

Problems with a conformation assignment of aryl-substituted resorc[4]arenes

2011 ◽  
Vol 76 (10) ◽  
pp. 1199-1222 ◽  
Author(s):  
Jakub Kaminský ◽  
Hana Dvořáková ◽  
Jan Štursa ◽  
Jitka Moravcová
Keyword(s):  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Quantum Chemical Calculations ◽  
Dynamic Process ◽  
Quantum Chemical ◽  
Energy Barrier ◽  
Π Interactions ◽  
Temperature Range ◽  
Acid Catalyzed

Acid-catalyzed condensation of resorcinol with 3,5-diisopropoxybenzaldehyde and 3,5-dihydroxybenzaldehyde afforded aryl substituted resorc[4]arenes 1a and 1b, respectively. All 16 hydroxyls in 1b were acetylated providing resorc[4]arene 1c. The conformational behaviour of 1a, 1b and 1c was studied by NMR spectroscopy and quantum chemical calculations. It was found that the stabilization of their conformations is an effect of competing π-π and OH-π interactions, hydrogen bonding and steric features, respectively. As a result, C2 symmetrical boat conformations 1a, 1b and 1c with aryls in axial positions were identified in all cases. In case of 1c also the formation of C2 symmetrical conformation with aryls in equatorial positions (boat-eq) was identified. Moreover, compounds 1a and 1b being able to create hydrogen bonds, adopt also symmetrical C4 crown conformations. For 1c(boat-ax), the boat-boat conversion with energy barrier of 80 kJ/mol was observed, while the 1c(boat-eq) was found to be rigid in the whole accessible temperature range. Both conformers of 1c exhibit also second dynamic process – rotation of bridge aryl rings (ΔG‡ = 66 kJ/mol).

Preparation, Crystal Structure and Spectroscopic Characterization of [Ga(OH)(SO4)(terpy)(H2O)] · H2O (terpy=2,2’:6’,2-Terpyridine): The First Characterized Gallium(III) Sulfato Complex

2004 ◽  
Vol 59 (3) ◽  
pp. 291-297 ◽  
Author(s):  
Andreas Sofetis ◽  
Giannis S. Papaefstathiou ◽  
Aris Terzis ◽  
Catherine P. Raptopoulou ◽  
Theodoros F. Zafiropoulos
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Good Yield ◽  
Spectroscopic Data ◽  
Spectroscopic Characterization ◽  
X Ray ◽  
X Ray Crystallography ◽  
H Nmr

The reaction of Ga2(SO4)3·18H2O and excess 2,2′:6′,2″-terpyridine (terpy) in MeOH / H2O leads to [Ga(OH)(SO4)(terpy)(H2O)]·H2O (1·H2O] in good yield. The structure of the complex has been determined by single-crystal X-ray crystallography. The GaIII atom in 1·H2O is 6-coordinate and ligation is provided by one terdentate terpy molecule, one monodentate sulfate, one terminal hydroxide and one terminal H2O molecule; the coodination polyhedron about the metal is described as a distorted octahedron. There is an extensive hydrogen-bonding network in the crystal structure which generates corrugated layers parallel to bc. The new complex was characterized by IR and 1H NMR spectroscopy. The spectroscopic data are discussed in terms of the nature of bonding

scholarly journals Cationic all-halogen bonding rotaxanes for halide anion recognition

2017 ◽  
Vol 203 ◽  
pp. 245-255 ◽  
Author(s):  
Xiaoxiong Li ◽  
Jason Y. C. Lim ◽  
Paul D. Beer
Keyword(s):  
Halogen Bond ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Anion Binding ◽  
Halide Anion ◽  
H Nmr ◽  
Organic Solvent Media ◽  
Synthetic Strategy ◽  
Anion Selectivity ◽  
Active Metal

A family of cationic halogen bonding [2]rotaxanes have been synthesised via an active-metal template synthetic strategy. 1H NMR spectroscopic anion titration investigations reveal these interlocked host systems recognize halides selectively over oxoanions in aqueous–organic solvent media. Furthermore, systematically modulating the rigidity and size of the rotaxanes’ anion binding cavities via metal complexation, as well as by varying the number of halogen bond-donor groups in the axle component, was found to dramatically influence halide anion selectivity.

Synthesis, characterization, photophysics, and anion binding properties of gold(i) acetylide complexes with amide groups

2014 ◽  
Vol 38 (12) ◽  
pp. 6168-6175 ◽  
Author(s):  
Hua-Yun Shi ◽  
Jie Qi ◽  
Zhen-Ze Zhao ◽  
Wen-Juan Feng ◽  
Yu-Hao Li ◽  
...  
Keyword(s):  
Color Change ◽  
Amide Group ◽  
Anion Binding ◽  
Binding Properties

A mononuclear gold(i) acetylide complex with an amide group, 3a, shows a dramatic color change upon addition of F− in DMSO.

scholarly journals Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: 1H-MNR spectroscopic study

2003 ◽  
Vol 68 (1) ◽  
pp. 1-7 ◽  
Author(s):  
R. Markovic ◽  
A. Shirazi ◽  
Zdravko Dzambaski ◽  
Marija Baranac ◽  
Dragica Minic-Popovic
Keyword(s):  
Hydrogen Bonding ◽  
Nmr Spectroscopy ◽  
Hydrogen Bonds ◽  
Spectroscopic Study ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Solvent Polarity ◽  
Concentration Effect ◽  
Intermolecular Hydrogen Bonding ◽  
Dynamic 1H Nmr

Application of dynamic 1H-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied.

Sign in / Sign up

Export Citation Format

Share Document