CUCURBIT(7)URIL

Base Information

• Chemical Name: CUCURBIT(7)URIL
• CAS No.: 259886-50-5
• Molecular Formula: C42H42N28O14
• Molecular Weight: 1162.97
• European Community (EC) Number: 811-749-5
• DSSTox Substance ID: DTXSID301316938
• Nikkaji Number: J1.256.301I,J1.590.904H
• Wikidata: Q27122604
• Metabolomics Workbench ID: 57745
• ChEMBL ID: CHEMBL3770339
• Mol file: 259886-50-5.mol

Synonyms:Cucurbit[7]uril;Curcubit[7]uril;

Chemical Property of CUCURBIT(7)URIL

Chemical Property:

• PKA: 0.09±0.20(Predicted)
• PSA: 329.70000
• Density: 2.69 g/cm³
• LogP: -8.34680
• XLogP3: -8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 0
• Exact Mass: 1162.34352813
• Heavy Atom Count: 84
• Complexity: 2540

Purity/Quality:

97% ^*data from raw suppliers

Cucurbit[7]uril (CB[7]) hydrate, 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1N2C3C4N(C2=O)CN5C6C7N(C5=O)CN8C9C2N(C8=O)CN5C8C%10N(C5=O)CN5C%11C%12N(C5=O)CN5C%13C%14N(C5=O)CN5C%15C(N1C5=O)N1CN3C(=O)N4CN6C(=O)N7CN9C(=O)N2CN8C(=O)N%10CN%11C(=O)N%12CN%13C(=O)N%14CN%15C1=O
• General Description: Cucurbit[7]uril (CB[7]) is a macrocyclic host molecule with a hydrophobic cavity that selectively binds cationic and aromatic guests, forming stable inclusion complexes in aqueous solution. Its structure features carbonyl-lined portals that interact with charged guest moieties while encapsulating hydrophobic cores within the cavity. CB[7] exhibits high binding affinity for guests with appropriately spaced cationic groups, making it useful for applications in molecular recognition, sensors, and supramolecular chemistry.

Technology Process of CUCURBIT(7)URIL

There total 32 articles about CUCURBIT(7)URIL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C42H42N28O14*C7H8N4O2 → theophylline (58-55-9,75448-53-2) + cucurbituril (259886-50-5)

Guidance literature:

In water; Solvent; Equilibrium constant;

DOI:10.1039/d1tc02004h

Reference yield:

cucurbit[7]uril methylviologen dichloride 1:1 inclusion complex → paraquat dichloride (1910-42-5) + cucurbituril (259886-50-5)

Guidance literature:

With Tris buffer; sodium chloride; In water; at 25 ℃; pH=7.2; Further Variations:; Reagents; Equilibrium constant;

DOI:10.1021/jo035030+

Reference yield:

C42H42N28O14*C16H36P(1+)*Cl(1-) → tetra-n-butylphosphonium chloride (2304-30-5) + cucurbituril (259886-50-5)

Guidance literature:

In methanol; water; Equilibrium constant;

DOI:10.1007/s10847-020-01006-w

upstream raw materials:

formaldehyd

glycouril

glycoluril dimer

glycoluril tetramer

Downstream raw materials:

C₁₆H₁₄N₄*C₄₂H₄₂N₂₈O₁₄

Refernces

Cucurbit[7]uril host-guest complexes with cationic bis(4,5-dihydro-1H- imidazol-2-yl) guests in aqueous solution

10.1139/V06-099

Cucurbit[7]uril (CB[7]) is a macrocyclic host molecule with a hydrophobic cavity that has a strong affinity for aromatic and adamantyl guests, particularly when these guests contain cationic substituents. CB[7] is part of the cucurbituril family, formed in acid-catalyzed condensation reactions of glycoluril with paraformaldehyde. It has similarly sized hydrophobic cavities as the more well-studied a-, ?-, and ?-cyclodextrins but differs in the nature and size of the portals to the cavities, which are lined with ureido carbonyl groups. The research investigates the host–guest interactions between cucurbit[7]uril (CB[7]) and a series of novel cationic bis(4,5-dihydro-1H-imidazol-2-yl) guests in aqueous solution. The purpose is to explore the stability and characteristics of the inclusion complexes formed, which have potential applications in various chemical processes. The researchers employed UV–vis and NMR spectroscopy, and electrospray mass spectrometry to study these interactions. The results showed that most guests formed very stable inclusion complexes with CB[7], except for 1,3-bis(4,5-dihydro-1H-imidazol-2-yl)adamantane, which binds externally. The stability constants and complexation-induced shifts (CIS) were correlated with the nature of the guest core and the distance between the charges on the terminal rings. The study concludes that the hydrophobic core of the guest resides within the CB[7] cavity, while the charged units remain outside, adjacent to the carbonyl-lined portals. This research provides valuable insights into the binding behaviors and stability of these host–guest complexes, which could be useful for developing new applications in photochemical reactions, molecular shuttles, and sensors.