Why is the fluorine atom a poor hydrogen bond acceptor?

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Discussion Overview

The discussion revolves around the nature of fluorine as a hydrogen bond acceptor (HBA) and the factors influencing its ability to participate in hydrogen bonding. Participants explore the implications of fluorine's electronegativity, its lone pairs of electrons, and the strength of hydrogen bonds in various contexts, including both elemental fluorine and fluorine-containing compounds.

Discussion Character

  • Debate/contested
  • Conceptual clarification
  • Technical explanation

Main Points Raised

  • Some participants propose that fluorine's high electronegativity causes it to hold onto its lone pairs too tightly, making it a poor hydrogen bond acceptor.
  • Others argue that the presence of strong hydrogen bonds in the ion FHF- contradicts the claim that fluorine cannot accept hydrogen bonds effectively.
  • A participant questions the clarity of the statement regarding fluorine's electronegativity and its implications for hydrogen bonding, suggesting that it may not apply to fluorine compounds like HF specifically.
  • Another participant emphasizes that fluorine has three lone pairs, which could participate in hydrogen bonding, raising questions about the original claim regarding elemental fluorine.

Areas of Agreement / Disagreement

Participants express differing views on fluorine's role as a hydrogen bond acceptor, with no consensus reached on the validity of the initial claims regarding its electronegativity and bonding capabilities.

Contextual Notes

The discussion includes assumptions about the nature of hydrogen bonding and the specific context of fluorine versus fluorine-containing compounds, which remain unresolved.

sgstudent
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My notes states that fluorine is too highly electronegative and hence clings on too tightly to its lone pair of electrons and so it cannot accept hydrogen bonds as well. However, it also stated that a hydrogen bond will be stronger if the electron density on the electron rich atom the stronger the hydrogen bond. These 2 statements seem to contradict though.

I read online from this link http://www.quora.com/Why-can-chlorine-atoms-not-form-hydrogen-bonds-even-though-they-have-very-similar-electronegativity-to-nitrogen-which-can that a hydrogen bond has an electrostatic component, but what differentiates it from a dipole-dipole interaction is that it also has a covalent component. And since the F clings onto its electrons too tightly it would not want to form a covalent bond which is why its a poor HBA and forms weak hydrogen bonds.

So is the second statement wrong?
 
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sgstudent said:
My notes states that fluorine is too highly electronegative and hence clings on too tightly to its lone pair of electrons and so it cannot accept hydrogen bonds as well.
I wouldn't sign that. The hydrogen bond in the ion FHF##^-## is one of the strongest known.
 
It's not clear what this statement means: "fluorine is too highly electronegative and hence clings on too tightly to its lone pair of electrons and so it cannot accept hydrogen bonds as well."

Fluorine, atomic number 9, has 7 electrons in its valence shell, hence it is lacking 1 electron to have a full complement, which is why it is grouped with the halogens in the Periodic Table.
 
SteamKing said:
Fluorine, atomic number 9, has 7 electrons in its valence shell, hence it is lacking 1 electron to have a full complement, which is why it is grouped with the halogens in the Periodic Table.
And how does this contradict the fact that fluorine, also has lone pairs that participate in hydrogen bonding?
I think it is also amply clear from the context that sgstudent is not talking about a fluorine atom but some fluorine compounds like HF.
 
DrDu said:
And how does this contradict the fact that fluorine, also has lone pairs that participate in hydrogen bonding?
I think it is also amply clear from the context that sgstudent is not talking about a fluorine atom but some fluorine compounds like HF.
That's funny, because his notes didn't say anything about fluorine compounds, just fluorine.
 
Even a fluorine atom has 3 lone pairs ...
 

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