Questions tagged [hydrogen-bond]

Bond between covalently bound hydrogen atom and atom possessing a lone pair of electrons.

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2answers
26k views

Why is HCl not considered to have hydrogen bonding?

A molecule that has hydrogen bonding usually follows these two premises. 1.) There is a hydrogen atom involved 2.) Hydrogen must be bonded to a highly electronegative element which are ...
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Why does the gauche conformation of ethane-1,2-diol show hydrogen bonding?

Why does the gauche conformation of ethane-1,2-diol show hydrogen bonding even though there is no 6-membered ring system? If we don't consider one of the $\ce{H}$ (which is what is usually done), then ...
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1answer
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Theoretical model for the hydrogen bond

I am curious how, from the perspective of quantum chemistry, the hydrogen bond is modeled. In particular I am interested in using such a model to estimate the amount of energy released per $\ce{H2O}$ ...
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Length of C-H bonds in hybridized bonding orbitals

What is the effect of hybridization and double-bond formation on the rest of the atoms/molecules attached to the central atom? For example, in a benzene molecule, the Carbon-Carbon bonds are ...
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1answer
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Why is a ketone not capable of hydrogen bonding among themselves?

The ketone has one oxygen atom in it and there are two lone pairs hanging out, both of which make it seemingly capable of hydrogen bonding. But in reality it is not. Did some research and found this ...
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Which intermolecular interaction is dependent on the inverse cube of distance?

The intermolecular interaction that is dependent on the inverse cube of distance between molecules is: hydrogen bond ion-ion interaction ion-dipole interaction London force Inverse ...
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1answer
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Does intramolecular hydrogen bonding occur in dicarboxylic acids?

Consider ethanedioic acid: Could it form intramolecular hydrogen bonds (between the C=O and HO)?
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When does hydrogen bonding happen?

What kinds of molecules will experience hydrogen bonding (inter and intra)? Why does it occur for some H atoms but not others?
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Volatile nature due to hydrogen bonding

Why does intramolecular hydrogen bonding make an organic (or possibly inorganic as well(?)) compound volatile. What I think is that it might be due to decrease in the solubility of the compound as ...
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1answer
934 views

Hydrogen bond comparison

How do you compare the strength of H bonds when it's the same atom on both sides of the H? Like $\ce{N-H\bond{...}N}$ vs $\ce{F-H\bond{...}F}$? Is one still stronger than the other, or are they both ...
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Is a hydrogen bond considered to be a van der Waals force?

Is a hydrogen bond considered to be a Van der Waals force?
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How to tell if a molecule will participate in hydrogen bonding with water?

I was recently doing some organic chemistry work and came across a set of problems. "Which of the following compounds will participate in hydrogen bonding with water? For each compound, indicate ...
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1answer
192 views

If hydrogen bonding in water was weaker, what happens to H+ ion concentration?

Water ionization becomes much less evident if the hydrogen bonds are just a few percent stronger but pure water contains considerably more $\ce{H+}$ ions if they are few percent weaker. I found this ...
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Does hydrogen bonding strength correspond to Brønsted basicity in a given medium?

It does seem that there is a correlation. Both are measures of proton affinity. Heck, isn't hydrogen bonding present in the transition states of most acid base reactions (excluding those involving ...
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1answer
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Does the ammonium ion hydrogen bond with water?

What about oxonium ions, such as hydronium ion? Do these hydrogen bond with water? If we see hydrogen bonding as a purely electrostatic phenomenon, then why not? Ammonium ion still has nitrogen ...
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1answer
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Halogen bond definition

I was looking for an accurate definition of halogen bonding. I was able to find quite a few good ones, but none of them would explain if a X---H intermolecular interaction would count as a form of ...
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Is hydrogen bonding generally defined to include only three period two elements?

Traditionally, hydrogen bonding has been defined to only include interactions between a positively polarized hydrogen and three period-two elements: nitrogen, oxygen, and fluorine. Why was this ...
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1answer
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Why is hydrogen bonding more significant than any other interaction between dipoles?

Solvents can be categorized as polar and protic. I understand that to be protic there had to be a significantly polar bond involving a hydrogen atom. However, how is the a hydrogen bond different in ...
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Why does hydrogen bonding in salicylic acid make it more acidic?

When salicylic acid deprotonates (losing the proton from the carboxyl group) it forms a hydrogen bond with between the oxygen in the carboxylate anion and the hydrogen in the alcohol group. However, ...
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How can the hydrogen bonds in solid HF be best represented?

The hydrogen bonds in solid HF can be best represented as: The correct answer is supposed to be (c), but I don't understand why this is so. Does the strength of hydrogen bonding depend on the $\...
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Does hydrogen bonding only occur between water molecules?

Does hydrogen bonding only occur between water molecules? Is the dipole-dipole intermolecular interaction know as hydrogen bonding because it is between water molecules, or is called that because of ...
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1answer
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Which atoms in a given amino acid are able to form hydrogen bonds with water?

Can anyone help me with this question I have tried everything. I know hydrogen bonding is with $\ce{F}$, $\ce{O}$, or $\ce{N}$, but every time I select those is says it's wrong.
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Examples of intramolecular hydrogen bonding closing bond angles

Okay, we've established that intramolecular hydrogen bonding can exist in molecules, and doesn't always serve the purpose of closing the bond angle at least relative to other stereoisomers of the same ...
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SN1 Polar Protic Solvent Stabilization of Substrate

I know that the standard textbook answer is that a polar protic solvent is able to better stabilize/solvate carbocations through hydrogen bonding. I understand that a solvent such as water or ...
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How does intramolecular hydrogen bonding cause the molecules to be separated from each other?

I learnt about intramolecular hydrogen bonding today, which occurs between molecules such as ortho-nitrophenol. What I was told is that in case of intramolecular bonding, the molecules separate from ...
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Polymer Crystallinity

See the following question: I think the answer is A because of the hydrogen bond in the side group, thus the degree of secondary bonding between parallel chain segments is higher. Is my thinking ...
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249 views

How would you know if … is H-bond or permanent dipole or induced dipole?

For example like HCl, why isn't it a hydrogen bond?
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Effect of temperature on Hydrogen Bonding?

We had this question in a test and I am not sure of the answer Q. Temperature changes don't effect the extent of inter and intra molecular hydrogen bonding. State true or false. I think that ...
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1answer
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In which state does the bifluoride anion exist?

Statement 1. The $\ce{HF2-}$ ions exist in solid state and also in liquid state but not in aqueous state. Statement 2. The magnitude of hydrogen bonding between $\ce{HF}$ is weaker than that ...
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Do alkanes evaporate faster than alcohols?

If so, is it because alchohols have hydrogen bonds? Which type of compound evaporates faster, and why?
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Does hydrogen peroxide exhibit intramolecular hydrogen bonding interactions?

We know that intermolecular hydrogen bonding is seen in hydrogen peroxide $(\ce{H2O2})$. But is intramolecular H-bonding, i.e. hydrogen bond between an oxygen atom and a hydrogen atom attached to the ...
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What exactly is hydrogen bonding (and does it really need fluorine, oxygen, or nitrogen)?

I'm not satisfied with the rationale for the intermolecular attraction known as hydrogen bonding. In my book, it states that Hydrogen bonding is a special type of intermolecular attraction between ...
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Halflife of hydrogen bonds

Related: Covalent Bond/Hydrogen Bond What is the half-life of hydrogen bonds in a glass of water at room temperature, say 18 degrees Celsius? I guess values may be different for distilled water and ...
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Are metals hydrogen bond acceptors or donors?

In a carbonyl or $\ce{-OH}$ group, it's clear the oxygen acts as a hydrogen bond acceptor. Do metals act as hydrogen bond acceptors or donors and if so, how can I tell as what it's acting?
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Strength of intramolecular vs intermolecular hydrogen bonds

Why are intramolecular hydrogen bonds weaker than intermolecular hydrogen bonds?
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The effect of structure on the boiling points of organic molecules

Why do molecules like methoxyethane, ethoxyethane and so on have lower boiling points than isomeric alcohols? I think it has something to do with the structure, but I don't exactly know what it is.