Instruct: Given a question, retrieve documents that answer the question.
Query: How strong is a hydrogen bond?
A hydrogen bond (H-bond), is a specific type of interaction that involves dipole-dipole attraction between a partially positive hydrogen atom and a highly electronegative, partially negative oxygen, nitrogen, sulfur, or fluorine atom (not covalently bound to said hydrogen atom). It is not a covalent bond, but instead is classified as a strong non-covalent interaction. It is responsible for why water is a liquid at room temperature and not a gas (given water's low molecular weight). Most commonly, the strength of hydrogen bonds lies between 0 - 4 kcal/mol, but can sometimes be as strong as 40 kcal/mol In solvents such as chloroform or carbontetrachloride one observes e.g. for the interaction between amides additive values of about 5 kJ/mol. According to L. Pauling the strength of a hydrogen bond is essentially determined by the electrostatic charges. Measurements of thousands complexes in chloroform or carbontetrachloride have led to additive free energy increments for all kind of donor-acceptor combinations.
A symmetric hydrogen bond is a special type of hydrogen bond in which the proton is spaced exactly halfway between two identical atoms. The strength of the bond to each of those atoms is equal. It is an example of a 3-center 4-electron bond. This type of bond is much stronger than "normal" hydrogen bonds, in fact, its strength is comparable to a covalent bond. It is seen in ice at high pressure (Ice X), and also in the solid phase of many anhydrous acids such as hydrofluoric acid and formic acid at high pressure. It is also seen in the bifluoride ion [F−H−F]. Much has been done to explain the symmetric hydrogen bond quantum-mechanically, as it seems to violate the duet rule for the first shell: The proton is effectively surrounded by four electrons. Because of this problem, some consider it to be an ionic bond.
A hydrogen bond is a specific dipole where a hydrogen atom has a partial positive charge (δ+) to due a neighboring electronegative atom or functional group. Hydrogen bonds are amongst the strong intermolecular interactions know other than ion-dipole interactions. For intermolecular hydrogen bonds the δ+ hydrogen interacts with a δ- on an adjacent molecule. Examples of molecular solids that hydrogen bond are water, amino acids, and acetic acid. For acetic acid, the hydrogen (δ+) on the alcohol moiety of the carboxylic acid hydrogen bonds with other the carbonyl moiety (δ-) of the carboxylic on the adjacent molecule. This hydrogen bond leads a string of acetic acid molecules hydrogen bonding to minimize free energy. These strings of acetic acid molecules then stack together to build solids.
Although these properties are interrelated, they are not interdependent. A metal hydride can be a thermodynamically a weak acid and a weak H donor; it could also be strong in one category but not the other or strong in both. The H strength of a hydride also known as its hydride donor ability or hydricity corresponds to the hydride's Lewis base strength. Not all hydrides are powerful Lewis bases. The base strength of hydrides vary as much as the pKa of protons. This hydricity can be measured by heterolytic cleaving hydrogen between a metal complex and base with a known pK then measuring the resulting equilibrium. This presupposes that the hydride doesn't heterolytically or homolytically react with itself to reform hydrogen. A complex would homolytically react with itself if the homolytic M-H bond is worth less than half of the homolytic H-H bond. Even if the homolytic bond strength above that threshold the complex is still susceptible to radical reaction pathways.
High hydrogen adsorption enthalpy is also important. Theoretical studies have shown that 22-25 kJ/mol interactions are ideal for hydrogen storage at room temperature, as they are strong enough to adsorb H, but weak enough to allow for quick desorption. The interaction between hydrogen and uncharged organic linkers is not this strong, and so a considerable amount of work has gone in synthesis of MOFs with exposed metal sites, to which hydrogen adsorbs with an enthalpy of 5-10 kJ/mol. Synthetically, this may be achieved by using ligands whose geometries prevent the metal from being fully coordinated, by removing volatile metal-bound solvent molecules over the course of synthesis, and by post-synthetic impregnation with additional metal cations. (CH)V(CO)(H) and Mo(CO)(H) are great examples of increased binding energy due to open metal coordination sites; however, their high metal-hydrogen bond dissociation energies result in a tremendous release of heat upon loading with hydrogen, which is not favorable for fuel cells. MOFs, therefore, should avoid orbital interactions that lead to such strong metal-hydrogen bonds and employ simple charge-induced dipole interactions, as demonstrated in Mn[(MnCl)(BTT)].
At room temperature, hydrogen bromide is a colourless gas, like all the hydrogen halides apart from hydrogen fluoride, since hydrogen cannot form strong hydrogen bonds to the large and only mildly electronegative bromine atom; however, weak hydrogen bonding is present in solid crystalline hydrogen bromide at low temperatures, similar to the hydrogen fluoride structure, before disorder begins to prevail as the temperature is raised. Aqueous hydrogen bromide is known as hydrobromic acid, which is a strong acid (p"K" = −9) because the hydrogen bonds to bromine are too weak to inhibit dissociation. The HBr/HO system also involves many hydrates HBr·"n"HO for "n" = 1, 2, 3, 4, and 6, which are essentially salts of bromine anions and hydronium cations. Hydrobromic acid forms an azeotrope with boiling point 124.3 °C at 47.63 g HBr per 100 g solution; thus hydrobromic acid cannot be concentrated beyond this point by distillation.
Hydrogen chalcogenides (also chalcogen hydrides or hydrogen chalcides) are binary compounds of hydrogen with chalcogen atoms (elements of group 16: oxygen, sulfur, selenium, tellurium, and polonium). Water, the first chemical compound in this series, contains one oxygen atom and two hydrogen atoms, and is the most common compound on the Earth's surface.
Chemical compounds have a unique and defined chemical structure held together in a defined spatial arrangement by chemical bonds. Chemical compounds can be molecular compounds held together by covalent bonds, salts held together by ionic bonds, intermetallic compounds held together by metallic bonds, or the subset of chemical complexes that are held together by coordinate covalent bonds. Pure chemical elements are generally not considered chemical compounds, failing the two or more atom requirement, though they often consist of molecules composed of multiple atoms (such as in the diatomic molecule H, or the polyatomic molecule S, etc.). Many chemical compounds have a unique numerical identifier assigned by the Chemical Abstracts Service (CAS): its CAS number.
Any substance consisting of two or more different types of atoms (chemical elements) in a fixed stoichiometric proportion can be termed a "chemical compound"; the concept is most readily understood when considering pure chemical substances. It follows from their being composed of fixed proportions of two or more types of atoms that chemical compounds can be converted, via chemical reaction, into compounds or substances each having fewer atoms. The ratio of each element in the compound is expressed in a ratio in its chemical formula. A chemical formula is a way of expressing information about the proportions of atoms that constitute a particular chemical compound, using the standard abbreviations for the chemical elements, and subscripts to indicate the number of atoms involved. For example, water is composed of two hydrogen atoms bonded to one oxygen atom: the chemical formula is HO. In the case of non-stoichiometric compounds, the proportions may be reproducible with regard to their preparation, and give fixed proportions of their component elements, but proportions that are not integral [e.g., for palladium hydride, PdH (0.02 < x < 0.58)].
Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. A hydroxide attached to a strongly electropositive center may itself ionize, liberating a hydrogen cation (H), making the parent compound an acid.
Fluoroantimonic acid is an inorganic compound with the chemical formula (also written , 2HF·SbF, or simply HF-SbF). It is an extremely strong acid, easily qualifying as a superacid. The Hammett acidity function, "H", has been measured for different ratios of HF:SbF. While the "H" of pure HF is −15, addition of just 1 mol % of SbF lowers it to around −20. However, further addition of SbF results in rapidly diminishing returns, with the "H" reaching −21 at 10 mol %. The use of an extremely weak base as indicator shows that the lowest attainable "H", even with > 50 mol % SbF, is somewhere between −21 and −23.
Hydrogen is found in the first group and first period in the periodic table, i.e. it is the first element on the periodic table, making it the lightest element. Since hydrogen gas is so light, it rises in the atmosphere and is therefore rarely found in its pure form, H. In a flame of pure hydrogen gas, burning in air, the hydrogen (H) reacts with oxygen (O) to form water (HO) and releases energy.
Because all amino acids contain amine and carboxylic acid functional groups, they share amphiprotic properties. Below pH 2.2, the predominant form will have a neutral carboxylic acid group and a positive α-ammonium ion (net charge +1), and above pH 9.4, a negative carboxylate and neutral α-amino group (net charge −1). But at pH between 2.2 and 9.4, an amino acid usually contains both a negative carboxylate and a positive α-ammonium group, as shown in structure (2) on the right, so has net zero charge. This molecular state is known as a zwitterion, from the German "" meaning "hermaphrodite" or "hybrid". The fully neutral form (structure (1) on the left) is a very minor species in aqueous solution throughout the pH range (less than 1 part in 10). Amino acids exist as zwitterions also in the solid phase, and crystallize with salt-like properties unlike typical organic acids or amines.
A chemical formula is a way of expressing information about the proportions of atoms that constitute a particular chemical compound, using the standard abbreviations for the chemical elements, and subscripts to indicate the number of atoms involved. For example, water is composed of two hydrogen atoms bonded to one oxygen atom: the chemical formula is HO. Many chemical compounds have a unique numerical identifier assigned by the Chemical Abstracts Service (CAS): its CAS number.
The alkali metals are among the most electropositive elements on the periodic table and thus tend to bond ionically to the most electronegative elements on the periodic table, the halogens (fluorine, chlorine, bromine, iodine, and astatine), forming salts known as the alkali metal halides. The reaction is very vigorous and can sometimes result in explosions. All twenty stable alkali metal halides are known; the unstable ones are not known, with the exception of sodium astatide, because of the great instability and rarity of astatine and francium. The most well-known of the twenty is certainly sodium chloride, otherwise known as common salt. All of the stable alkali metal halides have the formula MX where M is an alkali metal and X is a halogen. They are all white ionic crystalline solids that have high melting points. All the alkali metal halides are soluble in water except for lithium fluoride (LiF), which is insoluble in water due to its very high lattice enthalpy. The high lattice enthalpy of lithium fluoride is due to the small sizes of the Li and F ions, causing the electrostatic interactions between them to be strong: a similar effect occurs for magnesium fluoride, consistent with the diagonal relationship between lithium and magnesium.
The solubility in water of the other hydroxides in this group increases with increasing atomic number. Magnesium hydroxide Mg(OH) is a strong base (up to the limit of its solubility, which is very low in pure water), as are the hydroxides of the heavier alkaline earths: calcium hydroxide, strontium hydroxide, and barium hydroxide. A solution or suspension of calcium hydroxide is known as limewater and can be used to test for the weak acid carbon dioxide. The reaction Ca(OH) + CO Ca + + OH illustrates the basicity of calcium hydroxide. Soda lime, which is a mixture of the strong bases NaOH and KOH with Ca(OH), is used as a CO absorbent.
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) composed of atoms from more than one element held together by chemical bonds. A chemical element bonded to an identical chemical element is not a chemical compound since only one element, not two different elements, is involved.
A compound can be converted to a different chemical composition by interaction with a second chemical compound via a chemical reaction. In this process, bonds between atoms are broken in both of the interacting compounds, and then bonds are reformed so that new associations are made between atoms. Schematically, this reaction could be described as , where A, B, C, and D are each unique atoms; and AB, AD, CD, and CB are each unique compounds.
Hydrogen, being the lightest existing gas (7% the density of air), seems to be the most appropriate gas for lifting. But hydrogen has several disadvantages:
Hassium is a synthetic chemical element with symbol Hs and atomic number 108. It is named after the German state of Hesse. It is a synthetic element and radioactive; the most stable known isotope, Hs, has a half-life of approximately 10 seconds.
X-rays range in wavelength from 10 to 0.01 nanometers; a typical wavelength used for crystallography is 1 Å (0.1 nm), which is on the scale of covalent chemical bonds and the radius of a single atom. Longer-wavelength photons (such as ultraviolet radiation) would not have sufficient resolution to determine the atomic positions. At the other extreme, shorter-wavelength photons such as gamma rays are difficult to produce in large numbers, difficult to focus, and interact too strongly with matter, producing particle-antiparticle pairs. Therefore, X-rays are the "sweetspot" for wavelength when determining atomic-resolution structures from the scattering of electromagnetic radiation.
Hydrogen bond-assisted supramolecular assembly is the process of assembling small organic molecules to form large supramolecular structures by non-covalent hydrogen bonding interactions. The directionality, reversibility, and strong bonding nature of hydrogen bond make it an attractive and useful approach in supramolecular assembly. Functional groups such as carboxylic acids, ureas, amines, and amides are commonly used to assemble higher order structures upon hydrogen bonding.
The X−H distance is typically ≈110 pm, whereas the H···Y distance is ≈160 to 200 pm. The typical length of a hydrogen bond in water is 197 pm. The ideal bond angle depends on the nature of the hydrogen bond donor. The following hydrogen bond angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:
Strong hydrogen bonds are revealed by downfield shifts in the H NMR spectrum. For example, the acidic proton in the enol tautomer of acetylacetone appears at δ15.5, which is about 10 ppm downfield of a conventional alcohol.
The hydrogen bond is often described as an electrostatic dipole-dipole interaction. However, it also has some features of covalent bonding: it is directional and strong, produces interatomic distances shorter than the sum of the van der Waals radii, and usually involves a limited number of interaction partners, which can be interpreted as a type of valence. These covalent features are more substantial when acceptors bind hydrogens from more electronegative donors.
Many polymers are strengthened by hydrogen bonds within and between the chains. Among the synthetic polymers, a well characterized example is nylon, where hydrogen bonds occur in the repeat unit and play a major role in crystallization of the material. The bonds occur between carbonyl and amine groups in the amide repeat unit. They effectively link adjacent chains, which help reinforce the material. The effect is great in aramid fibre, where hydrogen bonds stabilize the linear chains laterally. The chain axes are aligned along the fibre axis, making the fibres extremely stiff and strong.