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The best Lewis structure for an oxocarbenium ion contains an oxygen–carbon double bond, with the oxygen atom attached to an additional group and consequently taking on a formal positive charge. In the language of canonical structures (or "resonance"), the polarization of the π bond is described by a secondary carbocationic resonance form ...
Another class of oxonium ions encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R−C= + −R′ which forms a resonance structure with the fully-fledged carbocation R− + −O−R′ and is therefore especially stable:
A carbenium ion is a positive ion with the structure RR′R″C +, that is, a chemical species with carbon atom having three covalent bonds, and it bears a +1 formal charge. Carbenium ions are a major subset of carbocations , which is a general term for diamagnetic carbon-based cations.
Second, while oxidation occurred from the desired convex face of the silyl enol ether, the authors saw a significant number of overoxidation products that they attributed to the stability of the oxocarbenium ion intermediate under sodium bicarbonate buffered conditions.
They have the structure – O[(C=O)–O] n – and the molecular formula [C n O 2n+1] 2–. Whereas the carbonate dianion itself is well known, as found in many salts , many organic compounds containing esters of it have been made, and the parent carbonic acid is also well-known, higher homologs are substantially less stable.
The general catalytic mechanism involves activating the leaving group, stabilization of the oxocarbenium ion, and positioning of a water molecule. [10] Structural studies on human uracil DNA glycosylase (PDB 4KSN) suggests a base-flipping mechanism that requires a few key residues.
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The 2-Norbornyl cation is one of the best characterized carbonium ion. It is the prototype for non-classical ions. As indicated first by low-temperature NMR spectroscopy and confirmed by X-ray crystallography, [1] it has a symmetric structure with an RCH 2 + group bonded to an alkene group, stabilized by a bicyclic structure.
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