Mechanism of tautomerisation in AgCN and AgNC?

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Discussion Overview

The discussion revolves around the mechanism of tautomerization in silver cyanide (AgCN) and silver isocyanide (AgNC), and whether similar processes occur in potassium cyanide (KCN) and potassium isocyanide (KNC). Participants explore the definitions and distinctions between tautomerization and isomerization.

Discussion Character

  • Debate/contested

Main Points Raised

  • One participant requests a detailed mechanism for the tautomerization in AgCN and AgNC, questioning if the same applies to KCN and KNC.
  • Another participant challenges the notion of tautomerization, suggesting that the process in question may be more accurately described as isomerization.
  • A different participant asserts that dynamic equilibrium between constitutional isomers qualifies as tautomerization, seeking clarification on the mechanism involved.
  • One participant acknowledges a misunderstanding about tautomerization, noting that it is broader than just hydrogen exchange and relates to isomerization in KCN and HCN, while expressing uncertainty about more complex representations.
  • There is mention of a potential mechanism involving the excitation of the bending mode, but specifics are not provided.

Areas of Agreement / Disagreement

Participants do not reach a consensus on whether the processes in question should be classified as tautomerization or isomerization, indicating a lack of agreement on terminology and mechanisms.

Contextual Notes

Participants express uncertainty regarding the definitions and mechanisms involved, highlighting the need for clarity on the distinctions between tautomerization and isomerization.

Ansuman
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Can anyone give a detailed mechanism for the tautomerization in AgCN and AgNC and is the same possible in KCN and KNC ??
 
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I don't know what you mean by "detailed mechanism" here, but I can't tell you that this is not a tautomerization, simply an isomerization.
 
Dynamic equilibrium existing between two constitutional isomers is TAUTOMERIZATION( a specific type of isomerization), right, that's what is happening here, but can a mechanism be presented??
 
Apologies, I was wrong. I thought that tautomerization only applied when H was being exchanged, but looking in the IUPAC Gold Book, it is more general than that. That said, I always heard it referred to as isomerization in the case of KCN, and even HCN with which I am more familiar.

Apart from writing KCN##\rightleftharpoons##KNC, I don't know of anything more complicated. I always understood it as being due to the excitation of the bending mode.
 

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