Very strong organosuperbases formed by combining imidazole and guanidine bases: synthesis, structure, and basicity.

نویسندگان

  • Katarina Vazdar
  • Roman Kunetskiy
  • Jaan Saame
  • Karl Kaupmees
  • Ivo Leito
  • Ullrich Jahn
چکیده

New structural motives for organosuperbases, that are easy to prepare and highly basic are urgently required in many areas of chemistry. The synthesis of N,N'-bis(imidazolyl)guanidine bases (BIG bases) is reported. Their pKα  values are determined as 26.1-29.3 in THF. They are thus probably the strongest known phosphorous-free organic bases both in solution and in the gas phase. Calculations help to determine the structural and electronic factors giving rise to the high basicity.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

General Aspects of Organosuperbases

In the field of organic chemistry, a base is generally defined as a reagent capable of abstracting proton to yield a carbanion species. At a basic textbook level, organobases are normally limited to amines, which are categorized as very weak bases according to the above definition. The introduction of an imine function (1⁄4NH) to the a-carbon of amines affords more basic amine species, amidines...

متن کامل

A new class of organosuperbases, N-alkyl- and N-aryl-1,3-dialkyl-4,5-dimethylimidazol-2-ylidene amines: synthesis, structure, pK(BH+) measurements, and properties.

A series of stable organosuperbases, N-alkyl- and N-aryl-1,3-dialkyl-4,5-dimethylimidazol-2-ylidene amines, were efficiently synthesized from N,N'-dialkylthioureas and 3-hydroxy-2-butanone and their basicities were measured in acetonitrile. The derivatives with tert-alkyl groups on the imino nitrogen were found to be more basic than the tBuP(1) (pyrr) phosphazene base in acetonitrile. The origi...

متن کامل

One pot three-component synthesis of imidazole derivatives using NH3/NH4Cl

Imidazole is a planar, five membered heteroaromatic molecule with pyrrole type and pyridine type annular nitrogens. Several approaches are available of imidazoles from alpha halo ketones, aminonitrile, aldehyde ect. Reactivity of imidazole and benzimidazole is referred from sets of  resonance structure in which the dipolar contributors have finite importance. Imidazoles among the principal grou...

متن کامل

Total synthesis of (+)-cylindradine A.

Cylindradines A and B, members of the polycyclic pyrrole-imidazole alkaloids (PIAs), are the only congeners bearing a 3-carbamoylpyrrole unit among the PIAs. In this communication, we described a total synthesis of (+)-cylindradine A based on intramolecular Friedel-Crafts type cyclization of pyrrole-aldehyde and oxidative cyclization of tricyclic pyrrolopyrrolidine-guanidine with hypervalent io...

متن کامل

Novel Schiff Bases of Pyrrole: Synthesis, Experimental and Theoretical Characterizations, Fluorescent Properties and Molecular Docking

Some new Schiff-base compounds based on pyrrole were synthesized by the reaction of 2-amino-1-methyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile (1)with aromatic aldehydes (2a-2e) in ethanol/acetic acid at room temperature. The structures of the Schiff bases were characterized by full spectral data. The fluorescence emission intensity of the Schiff bases has bee...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Angewandte Chemie

دوره 53 5  شماره 

صفحات  -

تاریخ انتشار 2014