MadSci Network: Chemistry |
You are correct! Hydroflouric acid is a weak acid partly because of hydrogen bonding. It can not only hydrogen bond to itself, but also to water if it is in aqueous solution. Since the protons will be involved in hydrogen bonding, they are not free to move about in solution and affect pH (a measure of acid strength) - the protons will be attached through weak hydrogen bonds to flourine and the lone pairs of electrons on oxygen in a water molecule. We know that hydrogen bonding occurs within compounds that have a hydrogen atom bonded to either nitrogen, oxygen, or flourine. In fact, if we look at other halogen acids that cannot hydrogen bond (specifically HCl and HBr), we notice that both of these have boiling points in the negative range (HCl = -85.06 C, and HBr = -66.7 C), but HF has a boiling point of 19.5 C! We can use hydrogen bonding to explain the unusually high boiling point in addition to the relatively weak acidity. But as you said in your question, we can also look at the strength of the HF bond to show why it is not such a strong acid. HF has a bond dissociation energy of 569 kilojoules per mole (kJ/mol), meaning that it would take 569 kJ to break the H-F bond in one mole of HF molecules. That's alot of energy! But lets look at the other halogen acids. HCl only needs 431 kJ/mol, HBr requires 368 kJ/mol, and HI requires only 297 kJ/mol. Since HF requires more energy to break the H-F bond, it will not dissociate as easily as the others, and we know that stronger acids dissociate more easily, so HF cannot be as strong as the other halogen acids. When you ask why flourine doesn't just take an electron from hydrogen and ionize, things get a bit more complicated. First, there is really no bond that can be characterized as 100% ionic where one atom will completly take electrons from another. There will always be some electron sharing between elements involved in a chemical bond and hence some covalent character. The amount of sharing depends on a few things including the molecule's dipole moment and the average bond length. For HF, the ionic character is about 41% compared to 18% in HCl and 12% in HBr. We also have to remember that everything tries to reach a point of equilibrium, and while the equilibrium may tend towards the products (such as H+ and Cl- in the dissociation of HCl), there will almost always be some reactants present. Strong acids that produce lots of H+ in solution (like HCl, HBr, and some organic acids) burn the skin because H+ is such a reactive species. It will react with the carbon-carbon double bonds in your cell membranes and thus causes a burn. I'm not a biology expert, but i'm reasonably sure that after the cell membrane is damaged like that, the cell will probably burst. Carbon-carbon double bonds are just one example, but there are other bonds present in cells that will easily react with H+. The anions resulting from dissociation are usually so stable and unreactive (Cl- for example is very stable) that they will not damage the skin.
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