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Though it does go against your intuition, you've actually mentioned the answer in your question. Stibane has a higher boiling point than ammonia/azane on account of van der Waals interactions (owing to the larger size of the antimony atom). Our teacher had actually posed this question to us during my first year of high-school. All of us were incredulous ...

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If I understood you correctly, you are talking about the peptide bond nitrogens ($\ce{R-C(=O)-\color{red}{N}H-R}$). This is, reduced to its significant chemical functional group an amide, more precisely a carboxylic amide. The amide nitrogen technically has a lone pair and thus technically could function as a hydrogen bond acceptor when viewed alone. However,...

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It appears that perhaps water may have symmetric hydrogen bonds between oxygen atoms, but it would take at least 60 GPa of pressure to make water to bond like that. Article named very descriptively "Compression of Ice to 210 gigapascals: Infrared Evidence for a Symmetric Hydrogen-Bonded Phase" proves it: Protonated and deuterated ices ($\ce{H2O}$ and $\... 18 This question crossed my mind during a lab today because we were making$\ce{Ni(dmg)2}$, which is shown below. Well first, this is charged in some sense, but it is net-neutral. Also, the configuration shown above is only one way to draw it, and it seems as if everything should be symmetrical and thus that hydrogen should be equally shared between the two ... 16 I don't think there is any such traditional definition requiring$\ce{N}$,$\ce{O}$or$\ce{F}$. For example, in table 7 and the discussion thereof in Hydrogen Bonding Annual Review of Physical Chemistry Vol. 22: 347-385 the hydrogen bonding in the following species are discussed:$\ce{ClHCl^-}\ce{BrHBr^-}\ce{IHI^-}\ce{BrHCl^-}$as well as ... 15 According to the IUPAC gold book a van der Waals force is: The attractive or repulsive forces between molecular entities (or between groups within the same molecular entity) other than those due to bond formation or to the electrostatic interaction of ions or of ionic groups with one another or with neutral molecules. The term includes: dipole–dipole, ... 15 I think there are a variety of qualitative ways of looking at this: Perhaps the most obvious is that$\ce{H2O}$can form a greater number of hydrogen bonds due to having an equal numbers of hydrogen bond acceptors and donors. Each of the hydrogen atoms can be hydrogen bond acceptors; each of the lone pairs on the oxygen can be donors. In$\ce{HF}$however ... 14 Well, it turns out that this is a very active area of research. I will only summarize what I understand to be true about the covalent nature of the hydrogen bond, so I'm sure the explanation could be more detailed and potentially more accurate in some places (I hope someone gives a more detailed answer), but here's what I've got. As you said, it has been ... 13 At Wikipedia you find this structure (drawn by Benjah-bmm27 on Wikimedia Commons): So, the answer (c) is correct. Yomen Atassi correctly stated that in such a hydrogen bond the two electronegative partners and the hydrogen prefer a linear arrangement, as this maximizes the orbital overlap for the hydrogen bond. That the configuration (c) is preferred over (... 13 It is safe to say that there will always be intermolecular forces at play. At the time where you will consider these you should already have a good idea about the molecules involved in your system. Based on the composition and molecular structures you can make certain assumptions. In a molecule it is straight forward to estimate (bond) polarities based on ... 12 @Dissenter, you really need to stop asking questions like this. Once again you point out that the emperor has no clothes! :) It turns out that the mechanism of simple proton transfer is an active area of investigation. There is not a single yes or no answer that would adequately address your questions. But if this truth were told in the introductory ... 12 It can indeed hydrogen bond, this can (to a certain extent) be observed by NMR. Due to the internal hydrogen bonding, the phenolic proton is surprisingly consistent, and shows no dependence on concentration. Image reproduced from Basic one- and two-dimensional NMR spectroscopy, Wiley, 2010. 11 Molecules with inter-molecular hydrogen bonds tend to associate with one another, while molecules with intra-molecular hydrogen bonds tend to associate with themselves. Ortho- and para-nitrophenol are often used as examples of molecules with intra- and inter-molecular hydrogen bonds respectively (see picture). Because of their molecular structures the ... 11 The strength of a hydrogen bond somewhat depends on the$\ce{X-H\bond{...}X}$angle that the hydrogen-bonding hydrogen forms with the two electronegative elements$\ce{X}$. In our case, carboxylic acids or alcohols,$\ce{X} = \ce{O}$so the angle is$\ce{O-H\bond{...}O}$. The ideal angle for this fragment is$180^\circ$. As you have drawn for carboxylic ... 11 You are right, in a sense. A more accurate statement would be that as the temperature decreases, the average lifetime of a hydrogen bond increases. Thus, on average the liquid/solid/molecule will be more stable. This is because, as you point out, hydrogen bonds are weak enough to be broken by collisions due to thermal motions (translation and rotation). ... 11 It turns out that the opposite of what happens in polar solvents takes place when a non-polar solvent is used. At the same temperature, o-nitrophenol is more soluble in benzene than it's m and p isomers. Sidgwick et al.1 did a study of this and obtained the following results. (Note that the solvent they used was toluene and not benzene, but they are similar ... 11 The paper[1] referenced by Nilay Ghosh says that, it is well known that hydrogen bonds commonly exist in ammonia clusters and play an important role and gives a picture of some of the clusters that were assumed to exist. So there seems to be evidence of significant covalent hydrogen bonding in possible ammonia clusters, at least from the calculations. ... 10 Let me answer the second question first, because the answer is so much easier: Of course the hydrogen bond strength depends among others upon the carbon oxygen is attached to. Consider phenol and methanol or methanol and formic acid. The guess as to which hydrogen bond is stronger is — I have to admit it — my speculation. But I think that methanol should be ... 10 In Schaefer's paper,[1] which you linked, the authors describe nitromalonamide as being the compound with the lowest calculated barrier to intramolecular proton transfer, or tautomerisation. Earlier this month (Feb 2019), Perrins and Wu used NMR isotope shifts to show that nitromalonamide possesses a symmetric hydrogen bond.[2] This is "the first case, to ... 10 The boiling point of non-ionic compounds are highly depend on their H-bonding abilities. For example, boiling point of water (molar mass:$\pu{18.02 g/mol}$) is$\pu{100 ^\circ C}$at$\pu{1 atm}$while that of ethanol (molar mass:$\pu{46.07 g/mol}$) is$\pu{78.4 ^\circ C}$at$\pu{1 atm}$, even though ethanol is heavier and have more other intermolecular ... 9 Disclaimer: I am not a computational chemist, I am completely new to this stuff. Just a humble student of @pentavalentcarbon However, my thought is that if you have interacting OH groups, the hydrogen bonding would make the eclipsed conformations more stable. Is this be the case? Why or why not? For example, a small molecule containing two carbons, each ... 9 Your terminology is a little off: water isn't an element. There isn't really a simple single explanation of why some solids are less dense than their associated liquids. The general explanation (which doesn't really explain much) is that the solid has a structure and, sometimes, that structure takes us more space than the average structure that occurs in ... 9 The$\mathrm pK_\mathrm a$of the$\ce{CH2}$group in a dicarbonyl compound is roughly$10$, whereas the$\mathrm pK_\mathrm a$of a carboxylic acid is roughly$5$. For example, dimethyl malonate has a$\mathrm pK_\mathrm a$of$13$whereas acetic acid has a$\mathrm pK_\mathrm a$of$4.7$. So, the C–H bond acidity is not likely to be under consideration in ... 9 True, Indigo can form hydrogen bonds, but with what? Is it water? Nope. It makes hydrogen bonds with itself. This makes the molecule incapable of bonding with water. Not only that, but the molecule itself is quite symmetric, with oppositely oriented polar bonds, that cancel out each others' dipole moments. Notice the molecule's similarity to an ace of ... 9 Mathew Mahindaratne has provided analysis based on experimental values of the boiling points of the two compounds. I would like to offer a different view using bonding analysis. Before I begin tackling the question, we shall first clarify the concept of the hydrogen bond. While the popular view of the hydrogen bond is as a particularly strong type of "... 8 Yes. Temperature disrupts bond of all kinds. Heat up a protein hot enough and you can even disrupt its primary structure - the linear sequence of amino acids, and amino acids are held together through covalent bonds. This is why prion contaminated organisms and instruments must be heated to extremely, extremely high temperatures. The question is whether or ... 8 NO, Water is not only the example for hydrogen bonding. It's most common example for basics. Hydrogen bonds occur in DNA, proteins, polymers, etc. But for introductory level it is easy to explain with water. DNA: Hydrogen bonding between guanine and cytosine, one of two types of base pairs in DNA. Polymer: Para-aramid structure Images: Wikipedia 8 I know that the standard textbook answer is that a polar protic solvent is able to better stabilize/solvate carbocations through hydrogen bonding. In an$\ce{S_{N}1}\$ reaction, a polar protic solvent can stabilize the leaving group through both hydrogen bonding and solvent dielectric effects. While these same solvent dielectric effects can also ...

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Short answer: the ketone oxygen can participate in hydrogen bonding The compound you mention, methoxymethane, is an ether not a ketone. Ethers don't hydrogen bond very well because the oxygen isn't very polarized. On the other hand, the carbonyl in a ketone is polarized. We can draw resonance structures that show this polarization. (image source) ...

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I don't have the textbook you've gotten this from, but unless there's a statement to the contrary, I suspect these are intended as examples of hydrogen bonding, rather than an exhaustive list of the only hydrogen bonding pattern which can exist. If you start to look at real structures, you will see both "directions" of hydrogen bonding (hydroxyl donor/...

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