Cucurbituril-mediated supramolecular acid catalysis.
نویسندگان
چکیده
The rates of acid hydrolysis of N-benzoyl-cadaverine (1), mono-N-(tert-butoxy)carbonyl cadaverine (2), and benzaldoxime (3) with binding motifs for cucurbit[6]uril (1,2) and cucurbit[7]uril (1,3) were investigated in the absence and presence of these hosts. Significant rate enhancements (up to a factor of ca. 300 for the hydrolysis of 3) were observed. Competitive inhibition due to encapsulation of added cadaverine and the successful use of sub-stoichiometric amounts of macrocycle confirmed the function of cucurbiturils in promoting acid hydrolysis.
منابع مشابه
Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.
The supramolecular chemistry of cucurbituril, a synthetic receptor, is fascinating because of the remarkable guest binding behavior of the host. Studies in the field, however, have met with limitations, since the only species known was the hexameric macrocyclic compound, cucurbit[6]uril. Recently we synthesized its homologues, cucurbit[n]uril (n = 5, 7, 8), and derivatives. These new members of...
متن کاملSupramolecular Assemblies of Cucurbiturils with Photoactive, π‐conjugated Chromophores
Supramolecular assemblies of cucurbituril (CBn) homologues with p-conjugated chromophores will be overviewed. Special emphasis will be given to the effect of CBn on the optical properties of conjugated oligomers and polymers. How supramolecular complexes of p-conjugated chromophores including porphyrin derivatives, conjugated oligomers and polymers with CBn could be utilized in the theranostic ...
متن کاملGalactosylated cucurbituril-inclusion polyplex for hepatocyte-targeted gene delivery.
The work demonstrates a judicious approach to achieve hepatocyte cell-targeted highly efficient gene delivery by utilizing a supramolecular complex of galactosylated cucurbituril and dextran-spermine conjugates.
متن کاملSupramolecular Assemblies Constructed by Cucurbituril- Catalyzed Click Reaction
Efficient synthesis of novel materials with defined functions and properties, as well as the construction of nanometer-scale devices and machines, are highly desirable for many applications in nanotechnology, energy, and health care. To this end, supramolecular assemblies that can be constructed through non-covalent interactions, molecular recognition, and host–guest chemistry are very appealin...
متن کاملStimuli-responsive supramolecular micellar assemblies of cetylpyridinium chloride with cucurbit[5/7]urils.
This article demonstrates, for the first time, construction of novel cucurbituril (CB)-adorned supramolecular micellar assemblies of a cationic surfactant, cetylpyridinium chloride (CPC), through noncovalent host-guest interactions. The distinct cation receptor features and cavity dimensions of the CB5 and CB7 homologues assert that the macrocyclic hosts remain complexed with the CPC monomers a...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 11 12 شماره
صفحات -
تاریخ انتشار 2009