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The nitrogen center of pyridine features a basic lone pair of electrons. This lone pair does not overlap with the aromatic π-system ring, consequently pyridine is basic, having chemical properties similar to those of tertiary amines. Protonation gives pyridinium, C 5 H 5 NH +.The pK a of the conjugate acid (the pyridinium cation) is 5.25.
It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids. [3] As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions.
Basic aromatic compounds get protonated and form aromatic cations (e.g. pyridinium) under acidic conditions. Typical examples of basic aromatic rings are pyridine or quinoline. Several rings contain basic as well as non-basic nitrogen atoms, e.g. imidazole and purine.
Containing a pyridinium ion, pyridinium chloride has a pK a of approximately 5, slightly more acidic than that of typical amines. This is due to the hybridization of the nitrogen: the nitrogen is sp 2 hybridized and more electronegative than those nitrogens in ammonium cations, which are sp 3 hybridized. Hence they are stronger acids than ...
Structure of CrO(O 2) 2 (pyridine).Hydrogen atoms bonded to carbon atoms are omitted. Color code: Cr = gray, C= black, H = white, O= red, N = blue. Chromium(VI) oxide peroxide is formed by the addition of acidified hydrogen peroxide solutions to solutions of metal chromates or dichromates, such as sodium chromate or potassium dichromate.
One family of reagents employs the complex CrO 3 (pyridine) 2. [2] Sarett's reagent: a solution of CrO 3 (pyridine) 2 in pyridine. It was popularized for selective oxidation of primary and secondary alcohols to carbonyl compounds. Collins reagent is a solution of the same CrO 3 (pyridine) 2 but in dichloromethane. The Ratcliffe variant of ...
In fact, the addition of acid (H+) or hydroxide (OH-) acts to attenuate protodeboronation by shifting the speciation away from the reactive zwitterion. It is important to note that not all basic heteroaromatic boronic acids are reactive through a zwitterionic intermediate. Scheme for the speciation of 2-pyridine boronic acid in aqueous solution
The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet for this chemical from a reliable source such as eChemPortal, and follow its directions.