Hyperconjugation: Is it a Co-ordinate Bond?

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Discussion Overview

The discussion revolves around the concept of hyperconjugation and whether it can be classified as a coordinate bond. Participants explore the nature of hyperconjugation in relation to carbonium ions of varying stability and the similarities and differences between hyperconjugation and coordinate bonding.

Discussion Character

  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant questions if hyperconjugation can be defined as a coordinate bond, particularly in the context of carbonium ions.
  • Another participant suggests that while hyperconjugation and coordinate bonding share similarities, they differ in the nature of electron donation, with hyperconjugation involving partial donation of pi bond electron density.
  • A different viewpoint is presented, arguing that hyperconjugation does not qualify as a bond at all, and emphasizes the distinction between coordinate bonds formed from a full electron pair donation and other types of interactions.
  • There is mention of the ambiguity in classifying bonds in molecules like CCl4, which could arise from different bonding scenarios, including radical or ionic formations.

Areas of Agreement / Disagreement

Participants do not appear to reach a consensus on whether hyperconjugation qualifies as a coordinate bond, with multiple competing views expressed regarding the definitions and characteristics of these interactions.

Contextual Notes

The discussion highlights the semantic nuances in defining chemical bonds and interactions, particularly the lack of clarity in distinguishing between hyperconjugation and coordinate bonding based on electron donation mechanisms.

Karan Punjabi
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Guys, a certain chemical phenomenon known as hyperconjugation in which carbonium ion which is tertiary or secondary or primary in nature then the pi bond formed for stabilizing effect can be defined as a co ordinate bond or not?
 
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I'm not sure I'd refer to hyperconjugation as a coordinate bond, but it probably all boils down to semantics. You're onto something, though: the ideas of hyperconjugation and coordinate bonding are similar. In both cases you have systems where electrons from a filled orbital are donated into an empty orbital. Normally, what I see referred to as coordinate bonds (like between NH3 and BH3) involve the donation of a full electron pair, whereas in hyperconjugation, only a fraction of the pi bond electron density gets donated into the adjacent sigma antibond. It's more a difference of degree than a difference of kind.
 
Karan Punjabi said:
Guys, a certain chemical phenomenon known as hyperconjugation in which carbonium ion which is tertiary or secondary or primary in nature then the pi bond formed for stabilizing effect can be defined as a co ordinate bond or not?
I agree with TeethWhitener. I don't think a hyperconjugative interaction qualifies as a bond in the first place. But you likely learned in gen chem that a coordinate (or dative) covalent bond is a bond that was formed from a 2 e- interaction between a lewis acid and a lewis base. However, if you just look at a molecule by itself, e.g. CCl4, you can't say whether the bonds are dative or not. This molecule could be made from radicals or ions. Cl- + Cl3C+ --> CCl4 but Cl. + CCl3. -->
 

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