Can sulfur participate in a hydrogen bond?

In summary, there are conflicting answers about the presence of hydrogen bonding between thiols and alcohols. Some sources suggest that there is evidence of hydrogen bonding between these molecules, while others argue that it is weak or non-existent. This is due to the similarity in molecular structure between thiols and alcohols, and the fact that hydrogen bonding is not limited to just oxygen, fluorine, and nitrogen atoms. Rather, it exists on a continuum of bond polarity, with the strength of the bond decreasing as the electronegativity difference between the atoms decreases.
  • #1
gauss44
49
0
I googled it and got both answers, "yes" and "no."

What I mean is: O-H-S, F-H-S, N-H-S, etc.

Ex.'s of "yes": http://www.ncbi.nlm.nih.gov/pubmed/19089987 http://pubs.rsc.org/en/content/artic.../ce/c0ce00760a[/URL]

Ex. of "no": http://www.nature.com/nature/journal.../149218a0.html
 
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  • #2
Thiols and alcohols have similar molecular structure.
So there are (weak) hydrogen-bonding between individual thiol groups (R-SH)...
 
  • #3
Often hydrogen bonds are regarded as restricted to just O, F and N. But this is misleading as it's actually a polarity continuum from 0 bond dipole moment (only possible when the two atoms of the bond are identical) to purely ionic bonds (an idealization, but something like CsF is very close). It's also misleading because the electronegativity difference between F and N is greater than that between N and Cl or even N and S.
 

1. Can sulfur participate in a hydrogen bond?

Yes, sulfur can participate in a hydrogen bond under certain conditions. However, it is not a strong hydrogen bond donor or acceptor compared to other elements like oxygen or nitrogen.

2. How does sulfur participate in a hydrogen bond?

Sulfur can participate in a hydrogen bond through its lone pairs of electrons. It can act as a hydrogen bond acceptor, forming a weak bond with a hydrogen atom that is already bonded to an electronegative atom.

3. Can sulfur form multiple hydrogen bonds?

No, sulfur typically forms only one hydrogen bond at a time due to its larger atomic size and weaker electronegativity compared to other elements commonly involved in hydrogen bonding.

4. Can sulfur participate in intramolecular hydrogen bonding?

Yes, sulfur can participate in intramolecular hydrogen bonding in molecules that contain both a hydrogen bond donor and acceptor group on the sulfur atom. This type of bonding can affect the molecular structure and properties of the compound.

5. What are some examples of molecules with sulfur participating in a hydrogen bond?

Some examples of molecules with sulfur participating in a hydrogen bond include dimethyl sulfoxide (DMSO), thio-acidic acids, and some sulfur-containing amino acids such as cysteine and methionine.

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