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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.
Keeping this structure in mind, it makes sense that the substituent that can maintain positive charge the best would be most likely to migrate. [9] The higher the degree of substitution, the more stable a carbocation generally is. [10] Therefore, the tertiary > secondary > primary trend is observed. Resonance structures of the Criegee intermediate
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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.