Host-guest complexation of di-cyclohexanocucurbit[6]uril and hexa-cyclohexanocucurbit[6]uril with alkyldiammonium ions: a comparative study.

@article{Fang2016HostguestCO,
  title={Host-guest complexation of di-cyclohexanocucurbit[6]uril and hexa-cyclohexanocucurbit[6]uril with alkyldiammonium ions: a comparative study.},
  author={Guo-Sheng Fang and Wenqi Sun and Wenxuan Zhao and Rui-Lian Lin and Zhu Tao and Jing-Xin Liu},
  journal={Organic \& biomolecular chemistry},
  year={2016},
  volume={14 2},
  pages={
          674-679
        }
}
The host-guest complexation of symmetrical di-cyclohexanocucurbit[6]uril (Cy2Q[6]) and hexa-cyclohexanocucurbit[6]uril (Cy6Q[6]) with a series of alkyldiammonium ions (H(3+)N(CH(2))nNH(3+), n = 2-8) has been studied both in solution and in the gas phase. (1)H NMR data indicate that all alkyldiammonium ions have inclusion interactions with both hosts except for the ethanediammonium ion. In addition, if the alkyl chain of the alkyldiammonium ion is longer than n = 5 methylene groups, compressed… 
View on PubMed
rsc.org
12 Citations

12 Citations

Citation Type

Citation Type

Endo/exo binding of alkyl and aryl diammonium ions by cyclopentanocucurbit[6]uril
The binding interactions of CyP6Q[6] with a series of alkyl diammonium (+H3N(CH2)nNH3+, n = 2, 4, 6, 8, 10, 12) and aryl diammonium (p-phenylenediammonium and p-xylenediammonium) ions both in aqueous…
Binding interactions of bisbenzimidazolyl derivatives with cyclohexanocucurbit[6]uril
Abstract The binding properties of cyclohexanocucurbit[6]uril (Cy6Q[6]) host toward three 1,w-bisbenzimidazolyl derivatives (guests 1 – 3 , with alkyl chain of different lengths as linker) have been…
Study on the host–guest complex of dicyclohexanocucurbit[6]uril and 2-phenylbenzimidazole, and its recognition effect toward Fe3+
This paper has selected dicyclohexanocucurbit[6]uril (CyH2Q[6]) as the host and 2-phenylbenzimidazole (G) as the guest to investigate the host–guest interaction mode between CyH2Q[6] and G. Under…
Aniline-containing guests recognized by α,α’,δ,δ’-tetramethyl-cucurbit[6]uril host
TLDR
Experimental results indicate that both TMeQ[6] and Q[7] hosts can encapsulate aniline-containing guests to form stable inclusion complexes, but the oval cavity of TMe Q is more complementary in size and shape to the aromatic ring of the guests than the spherical cavity of Q.
Chiral and achiral crystals, charge-assisted hydrogen-bond patterns and self-organization of selected solid diaminium thiosulfates.
TLDR
An extended network of strong, charge-assisted hydrogen bonding of the +N-H...O- type is most likely the main factor defining crystal packing and the variable conformation of the cations, which seems to induce the formation of chiral solid-state structure from achiral components in the case of (4).
Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril
The interaction between cucuribit[10]uril (Q[10]) and a series of 4-pyrrolidinopyridinium salts bearing aliphatic substituents at the pyridinium nitrogen, namely 4-(C4H8N)C5H5NRBr, where R = Et (g1),…
Joint experimental and theoretical studies of the surprising stability of the aryl pentazole upon noncovalent binding to β-cyclodextrin.
TLDR
Binding of the β-cyclodextrin (β-CD) host to the unstable aryl pentazole guest has been confirmed experimentally and theoretically and the host-guest binding renders the enhancement of the nitrogen-ring aromatic character.
Supramolecular chemistry of substituted cucurbit[n]urils
Since the first example of substituted cucurbit[n]urils (Q[n]), decamethylcucurbit[5]uril (Me10Q[5]), was reported in 1992, numerous substituted Q[n]s have been synthesized and studied. In this…
Deciphering Noncovalent Interactions Accompanying 7,7,8,8-Tetracyanoquinodimethane Encapsulation within Biphene[n]arenes: Nucleus-Independent Chemical Shifts Approach.
TLDR
Binding of novel biphene[n]arene hosts to antiaromatic 7,7,8,8-tetracyanoquinodimethane (TCNQ) are investigated by DFT by employing nucleus-independent chemical shifts based profiles.
Encapsulation and removal of aniline by di-cyclohexanocucurbit[6]uril
The binding behaviors of Cy2Q[6] and Cy6Q[6] with aniline, p-methylaniline, and p-phenyldiamine were investigated by various techniques, which suggests that Cy2Q[6] is a promising candidate for…
...
1
2
...

References

SHOWING 1-10 OF 54 REFERENCES
1,3-Propanediammonium and 1,12-dodecanediammonium encapsulated in the cavity of symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril
The formation of host–guest inclusion complexes between symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril (TMeQ[6]) and two alkyldiammonium guests (1,3-propanediammonium and 1,12-dodecanediammonium)…
Contorted Conformations of 1,4‐Butylidenedipyridinium and 1,10‐Decylidenedipyridinium Cationic Guests in a Cucurbit[8]uril Host
1,4-Butylidenedipyridinium (C 4 DP 2+ ) and 1,10-decylidenedipyridinium (C 10 DP 2+ ) cationic guests form highly stable 1:1 inclusion complexes in aqueous solution with a cucurbit[8]uril (Q[8])…
Opposing substitution in cucurbit[6]urils forms ellipsoid cavities: the symmetrical dicyclohexanocucurbit[6]uril is no exception highlighted by inclusion and exclusion complexes
The symmetrical dicyclohexanocucurbit[6]uril has been synthesised by the controlled condensation of the diether of cyclohexanoglycoluril (1) and the dimer of glycoluril (2). The symmetrical…
Extended and contorted conformations of alkanediammonium ions in symmetrical α,α',δ,δ'-tetramethylcucurbit[6]uril cavity.
TLDR
ITC experiments show that the complexation of the alkyldiammonium guests with TMeQ[6] is mainly enthalpy driven, which benefits from ion-dipole interactions.
U-shaped conformation of alkyl chains bound to a synthetic receptor cucurbit[8]uril.
TLDR
The enthalpy-entropy compensation plot for the complexation suggests large conformational changes of the long alkyl chains and extensive dehydration associated with the inclusion complex formation.
Complexation of aliphatic ammonium ions with a water-soluble cucurbit[6]uril derivative in pure water: isothermal calorimetric, NMR, and X-ray crystallographic study.
TLDR
The thermodynamic parameters associated with the complexation are discussed in relation to the binding modes and conformations of the aliphatic chain of the guest molecules inside the host, which were investigated by 1H NMR spectroscopy and X-ray crystallography.
Complexation Thermodynamics of Cucurbit[6]uril with Aliphatic Alcohols, Amines, and Diamines
Using the isothermal calorimetric titration technique, we determined the stability constants (K), reaction enthalpy (ΔH°), and entropy (ΔS°) for complexation of cucurbit[6]uril (CB[6]) with a series…
Host-guest chemistry from solution to the gas phase: an essential role of direct interaction with water for high-affinity binding of cucurbit[n]urils.
TLDR
Gas phase structures obtained from density functional theory calculations, which support the results from the ion mobility measurements, and molecular dynamics simulated structures in water provide a detailed understanding of the solvated complexes.
The cucurbit[n]uril family.
In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae…
Toward reversible control of cucurbit[n]uril complexes.
  • A. Kaifer
  • Chemistry, Biology
    Accounts of chemical research
  • 2014
TLDR
The experimental results show that the thermodynamics and kinetics of the electron transfer reactions of these compounds can be substantially altered by complexation with CBn hosts, and therefore, electronTransfer reactions can be used to exert a measure of control on the overall binding affinity of the CBn complexes.
...
1
2
3
4
5
...