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Can Two of These Molecules Hydrogen Bond With Each Other?

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Partial intermolecular bonding interaction

Model of hydrogen bonds (1) between molecules of water

AFM image of napthalenetetracarboxylic diimide molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77  K.[one] ("Hydrogen bonds" in the pinnacle paradigm are exaggerated by artifacts of the imaging technique.[ii] [3])

A hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative atom or group, and another electronegative atom bearing a alone pair of electrons—the hydrogen bail acceptor (Air conditioning). Such an interacting system is mostly denoted Dn–H···Ac, where the solid line denotes a polar covalent bond, and the dotted or dashed line indicates the hydrogen bail.[iv] The almost frequent donor and acceptor atoms are the second-row elements nitrogen (N), oxygen (O), and fluorine (F).

Hydrogen bonds tin exist intermolecular (occurring between separate molecules) or intramolecular (occurring among parts of the same molecule).[5] [6] [7] [8] The free energy of a hydrogen bond depends on the geometry, the surroundings, and the nature of the specific donor and acceptor atoms, and tin can vary between i and twoscore kcal/mol.[ix] This makes them somewhat stronger than a van der Waals interaction, and weaker than fully covalent or ionic bonds. This blazon of bond tin can occur in inorganic molecules such as water and in organic molecules like Deoxyribonucleic acid and proteins. Hydrogen bonds are responsible for holding such materials every bit newspaper and felted wool together, and for causing dissever sheets of paper to stick together after becoming moisture and subsequently drying.

The hydrogen bond is responsible for many of the dissonant physical and chemical properties of compounds of N, O, and F. In particular, intermolecular hydrogen bonding is responsible for the high boiling bespeak of water (100 °C) compared to the other group-16 hydrides that have much weaker hydrogen bonds.[10] Intramolecular hydrogen bonding is partly responsible for the secondary and tertiary structures of proteins and nucleic acids. Information technology also plays an important office in the structure of polymers, both synthetic and natural.

Bonding [edit]

Definitions and general characteristics [edit]

A hydrogen atom attached to a relatively electronegative cantlet is the hydrogen bond donor.[12] C-H bonds but participate in hydrogen bonding when the carbon atom is bound to electronegative substituents, as is the case in chloroform, CHClthree.[xiii] In a hydrogen bond, the electronegative cantlet not covalently attached to the hydrogen is named the proton acceptor, whereas the one covalently bound to the hydrogen is named the proton donor. While this nomenclature is recommended by the IUPAC,[4] it can be misleading, since in other donor-acceptor bonds, the donor/acceptor assignment is based on the source of the electron pair (such nomenclature is too used for hydrogen bonds by some authors[9]). In the hydrogen bond donor, the H centre is protic. The donor is a Lewis base. Hydrogen bonds are represented as H···Y system, where the dots represent the hydrogen bail. Liquids that brandish hydrogen bonding (such as h2o) are called associated liquids.

Examples of hydrogen bail donating (donors) and hydrogen bond accepting groups (acceptors)

Cyclic dimer of acetic acid; dashed greenish lines represent hydrogen bonds

The hydrogen bond is often described equally an electrostatic dipole-dipole interaction. However, it too has some features of covalent bonding: information technology is directional and potent, produces interatomic distances shorter than the sum of the van der Waals radii, and usually involves a limited number of interaction partners, which can exist interpreted as a type of valence. These covalent features are more than substantial when acceptors bind hydrogens from more than electronegative donors.

As part of a more detailed list of criteria, the IUPAC publication acknowledges that the attractive interaction can arise from some combination of electrostatics (multipole-multipole and multipole-induced multipole interactions), covalency (charge transfer by orbital overlap), and dispersion (London forces), and states that the relative importance of each will vary depending on the arrangement. Even so, a footnote to the benchmark recommends the exclusion of interactions in which dispersion is the principal contributor, specifically giving Ar---CHiv and CH4---CH4 every bit examples of such interactions to exist excluded from the definition.[4] However, most introductory textbooks yet restrict the definition of hydrogen bail to the "classical" type of hydrogen bond characterized in the opening paragraph.

Weaker hydrogen bonds[xiv] are known for hydrogen atoms bound to elements such as sulfur (South) or chlorine (Cl); even carbon (C) can serve equally a donor, particularly when the carbon or one of its neighbors is electronegative (due east.g., in chloroform, aldehydes and terminal acetylenes).[15] [16] Gradually, it was recognized that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Air-conditioning with electronegativity approaching that of hydrogen (rather than being much more electronegative). Though these "non-traditional" hydrogen bonding interactions are oftentimes quite weak (~1 kcal/mol), they are also ubiquitous and are increasingly recognized as important control elements in receptor-ligand interactions in medicinal chemistry or intra-/intermolecular interactions in materials sciences.

The definition of hydrogen bonding has gradually broadened over time to include these weaker attractive interactions. In 2011, an IUPAC Task Grouping recommended a modern show-based definition of hydrogen bonding, which was published in the IUPAC journal Pure and Applied Chemistry. This definition specifies:

The hydrogen bond is an bonny interaction between a hydrogen atom from a molecule or a molecular fragment X–H in which Ten is more electronegative than H, and an cantlet or a group of atoms in the same or a different molecule, in which there is evidence of bond germination.[17]

Bond strength [edit]

Hydrogen bonds tin vary in force from weak (ane–2 kJ mol−1) to strong (161.5 kJ mol−1 in the ion HF −
two ).[xviii] [19] Typical enthalpies in vapor include:[20]

  • F−H···:F (161.5 kJ/mol or 38.six kcal/mol), illustrated uniquely by HFtwo −, bifluoride
  • O−H···:N (29 kJ/mol or 6.9 kcal/mol), illustrated water-ammonia
  • O−H···:O (21 kJ/mol or 5.0 kcal/mol), illustrated h2o-water, alcohol-alcohol
  • N−H···:N (13 kJ/mol or three.1 kcal/mol), illustrated by ammonia-ammonia
  • N−H···:O (8 kJ/mol or 1.9 kcal/mol), illustrated water-amide
  • OH +
    3     ···:OH
    two     (xviii kJ/mol[21] or iv.3 kcal/mol)

The strength of intermolecular hydrogen bonds is almost often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution.[22] The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is crystallography, sometimes besides NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can exist taken as indication of the hydrogen bond strength.

I scheme gives the following somewhat arbitrary classification: those that are xv to twoscore kcal/mol, 5 to xv kcal/mol, and >0 to 5 kcal/mol are considered strong, moderate, and weak, respectively.

Resonance assisted hydrogen bond [edit]

The resonance assisted hydrogen bail (commonly abbreviated as RAHB) is a strong type of hydrogen bond. It is characterized by the π-delocalization that involves the hydrogen and cannot be properly described by the electrostatic model alone. This description of the hydrogen bond has been proposed to describe unusually curt distances generally observed between O=C-OH∙∙∙ or ∙∙∙O=C-C=C-OH.[ commendation needed ]

Structural details [edit]

The Ten−H altitude 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 platonic bond bending depends on the nature of the hydrogen bail donor. The post-obit hydrogen bail angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:[23]

Acceptor···donor VSEPR geometry Angle (°)
HCN···HF linear 180
H2CO···HF trigonal planar 120
H2O···HF pyramidal 46
HtwoDue south···HF pyramidal 89
SO2···HF trigonal 142

Spectroscopy [edit]

Strong hydrogen bonds are revealed by downfield shifts in the iH NMR spectrum. For example, the acidic proton in the enol tautomer of acetylacetone appears at δH 15.five, which is about 10 ppm downfield of a conventional alcohol.[24]

In the IR spectrum, hydrogen bonding shifts the 10-H stretching frequency to lower energy (i.e. the vibration frequency decreases). This shift reflects a weakening of the X-H bail. Certain hydrogen bonds - improper hydrogen bonds - show a bluish shift of the X-H stretching frequency and a subtract in the bail length.[25] H-bonds tin too be measured by IR vibrational mode shifts of the acceptor. The amide I mode of backbone carbonyls in α-helices shifts to lower frequencies when they grade H-bonds with side-chain hydroxyl groups.[26]

Theoretical considerations [edit]

Hydrogen bonding is of persistent theoretical involvement.[27] Co-ordinate to a modern description O:H-O integrates both the intermolecular O:H lone pair ":" nonbond and the intramolecular H-O polar-covalent bond associated with O-O repulsive coupling.[28]

Breakthrough chemical calculations of the relevant interresidue potential constants (compliance constants) revealed[ how? ] large differences between individual H bonds of the aforementioned type. For example, the central interresidue North−H···N hydrogen bond betwixt guanine and cytosine is much stronger in comparison to the N−H···N bond between the adenine-thymine pair.[29]

Theoretically, the bond strength of the hydrogen bonds tin can be assessed using NCI index, non-covalent interactions index, which allows a visualization of these non-covalent interactions, as its name indicates, using the electron density of the system.

From interpretations of the anisotropies in the Compton profile of ordinary ice that the hydrogen bond is partly covalent.[30] However, this interpretation was challenged.[31]

Most more often than not, the hydrogen bail tin can exist viewed as a metric-dependent electrostatic scalar field between two or more intermolecular bonds. This is slightly dissimilar from the intramolecular bound states of, for example, covalent or ionic bonds; however, hydrogen bonding is mostly notwithstanding a bound country phenomenon, since the interaction energy has a internet negative sum. The initial theory of hydrogen bonding proposed by Linus Pauling suggested that the hydrogen bonds had a partial covalent nature. This interpretation remained controversial until NMR techniques demonstrated data transfer between hydrogen-bonded nuclei, a feat that would only be possible if the hydrogen bail contained some covalent grapheme.[32]

History [edit]

The concept of hydrogen bonding once was challenging.[33] Linus Pauling credits T. S. Moore and T. F. Winmill with the starting time mention of the hydrogen bail, in 1912.[34] [35] Moore and Winmill used the hydrogen bail to business relationship for the fact that trimethylammonium hydroxide is a weaker base than tetramethylammonium hydroxide. The clarification of hydrogen bonding in its improve-known setting, water, came some years later, in 1920, from Latimer and Rodebush.[36] In that paper, Latimer and Rodebush cite work by a fellow scientist at their laboratory, Maurice Loyal Huggins, saying, "Mr. Huggins of this laboratory in some work as yet unpublished, has used the idea of a hydrogen kernel held between two atoms equally a theory in regard to certain organic compounds."

Hydrogen bonds in small molecules [edit]

Crystal structure of hexagonal ice. Greyness dashed lines point hydrogen bonds

Water [edit]

A ubiquitous example of a hydrogen bond is found between water molecules. In a detached h2o molecule, there are ii hydrogen atoms and i oxygen atom. The simplest case is a pair of water molecules with 1 hydrogen bond between them, which is chosen the h2o dimer and is frequently used as a model organisation. When more molecules are present, every bit is the instance with liquid h2o, more than bonds are possible considering the oxygen of one h2o molecule has two alone pairs of electrons, each of which can form a hydrogen bond with a hydrogen on another water molecule. This can echo such that every h2o molecule is H-bonded with up to four other molecules, as shown in the effigy (two through its two lone pairs, and two through its two hydrogen atoms). Hydrogen bonding strongly affects the crystal structure of ice, helping to create an open hexagonal lattice. The density of ice is less than the density of water at the same temperature; thus, the solid phase of water floats on the liquid, unlike almost other substances.

Liquid water's high boiling point is due to the high number of hydrogen bonds each molecule tin form, relative to its low molecular mass. Owing to the difficulty of breaking these bonds, water has a very high boiling betoken, melting bespeak, and viscosity compared to otherwise similar liquids not conjoined by hydrogen bonds. H2o is unique because its oxygen atom has two solitary pairs and two hydrogen atoms, meaning that the full number of bonds of a water molecule is up to iv.

The number of hydrogen bonds formed past a molecule of liquid water fluctuates with time and temperature.[37] From TIP4P liquid h2o simulations at 25 °C, it was estimated that each h2o molecule participates in an average of 3.59 hydrogen bonds. At 100 °C, this number decreases to iii.24 due to the increased molecular motility and decreased density, while at 0 °C, the average number of hydrogen bonds increases to 3.69.[37] Another written report plant a much smaller number of hydrogen bonds: two.357 at 25 °C.[38] The differences may be due to the use of a different method for defining and counting the hydrogen bonds.

Where the bond strengths are more equivalent, one might instead find the atoms of ii interacting water molecules partitioned into 2 polyatomic ions of opposite charge, specifically hydroxide (OH−) and hydronium (HthreeO+). (Hydronium ions are also known as "hydroxonium" ions.)

H−O− H3O+

Indeed, in pure h2o nether weather condition of standard temperature and pressure level, this latter formulation is applicative merely rarely; on average near one in every 5.5 × 108 molecules gives up a proton to another h2o molecule, in accordance with the value of the dissociation abiding for water under such conditions. It is a crucial part of the uniqueness of water.

Because water may form hydrogen bonds with solute proton donors and acceptors, it may competitively inhibit the formation of solute intermolecular or intramolecular hydrogen bonds. Consequently, hydrogen bonds between or within solute molecules dissolved in water are near always unfavorable relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes.[39] Hydrogen bonds between water molecules have an average lifetime of 10−11 seconds, or 10 picoseconds.[xl]

Bifurcated and over-coordinated hydrogen bonds in h2o [edit]

A single hydrogen atom tin can participate in two hydrogen bonds, rather than one. This blazon of bonding is called "bifurcated" (separate in two or "two-forked"). Information technology tin exist, for example, in complex natural or synthetic organic molecules.[41] It has been suggested that a bifurcated hydrogen atom is an essential stride in water reorientation.[42]
Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (information technology is chosen overcoordinated oxygen, OCO) than are donor-blazon hydrogen bonds, first on the same oxygen'southward hydrogens.[43]

Other liquids [edit]

For example, hydrogen fluoride—which has iii lone pairs on the F atom but only 1 H atom—can form only ii bonds; (ammonia has the reverse problem: three hydrogen atoms merely merely 1 lone pair).

H−F···H−F···H−F

Further manifestations of solvent hydrogen bonding [edit]

  • Increment in the melting indicate, boiling point, solubility, and viscosity of many compounds can exist explained by the concept of hydrogen bonding.
  • Negative azeotropy of mixtures of HF and water
  • The fact that water ice is less dense than liquid h2o is due to a crystal structure stabilized by hydrogen bonds.
  • Dramatically higher boiling points of NH3, H2O, and HF compared to the heavier analogues PH3, H2Due south, and HCl, where hydrogen-bonding is absent.
  • Viscosity of anhydrous phosphoric acrid and of glycerol
  • Dimer formation in carboxylic acids and hexamer formation in hydrogen fluoride, which occur even in the gas stage, resulting in gross deviations from the ideal gas constabulary.
  • Pentamer formation of water and alcohols in apolar solvents.

Hydrogen bonds in polymers [edit]

Hydrogen bonding plays an of import role in determining the iii-dimensional structures and the properties adopted by many synthetic and natural proteins. Compared to the C-C, C-O, and C-N bonds that comprise most polymers, hydrogen bonds are far weaker, perhaps 5%. Thus, hydrogen bonds can exist cleaved by chemical or mechanical means while retaining the basic structure of the polymer backbone. This hierarchy of bond strengths (covalent bonds being stronger than hydrogen-bonds being stronger than van der Waals forces) is key to understanding the properties of many materials.[44]

DNA [edit]

In these macromolecules, bonding between parts of the aforementioned macromolecule crusade it to fold into a specific shape, which helps decide the molecule's physiological or biochemical role. For example, the double helical construction of DNA is due largely to hydrogen bonding betwixt its base pairs (as well as pi stacking interactions), which link 1 complementary strand to the other and enable replication.

Proteins [edit]

In the secondary structure of proteins, hydrogen bonds course betwixt the courage oxygens and amide hydrogens. When the spacing of the amino acrid residues participating in a hydrogen bond occurs regularly between positions i and i + iv, an alpha helix is formed. When the spacing is less, between positions i and i + 3, then a 3x helix is formed. When two strands are joined by hydrogen bonds involving alternate residues on each participating strand, a beta sheet is formed. Hydrogen bonds also play a part in forming the tertiary structure of poly peptide through interaction of R-groups. (See also protein folding).

Bifurcated H-bond systems are mutual in alpha-helical transmembrane proteins between the courage amide C=O of residue i every bit the H-bond acceptor and two H-bond donors from residue i+iv: the backbone amide N-H and a side-chain hydroxyl or thiol H+. The free energy preference of the bifurcated H-bond hydroxyl or thiol system is -three.4 kcal/mol or -2.six kcal/mol, respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-bondage, such equally serine, threonine, and cysteine within the hydrophobic membrane environments.[26]

The role of hydrogen bonds in poly peptide folding has also been linked to osmolyte-induced poly peptide stabilization. Protective osmolytes, such as trehalose and sorbitol, shift the protein folding equilibrium toward the folded state, in a concentration dependent manner. While the prevalent explanation for osmolyte activity relies on excluded volume effects that are entropic in nature, round dichroism (CD) experiments have shown osmolyte to deed through an enthalpic consequence.[45] The molecular mechanism for their role in protein stabilization is notwithstanding not well established, though several mechanisms have been proposed. Computer molecular dynamics simulations advise that osmolytes stabilize proteins by modifying the hydrogen bonds in the protein hydration layer.[46]

Several studies have shown that hydrogen bonds play an of import role for the stability between subunits in multimeric proteins. For case, a report of sorbitol dehydrogenase displayed an important hydrogen bonding network which stabilizes the tetrameric fourth construction within the mammalian sorbitol dehydrogenase protein family.[47]

A protein backbone hydrogen bail incompletely shielded from water attack is a dehydron. Dehydrons promote the removal of water through proteins or ligand bounden. The exogenous aridity enhances the electrostatic interaction betwixt the amide and carbonyl groups by de-shielding their partial charges. Furthermore, the aridity stabilizes the hydrogen bond by destabilizing the nonbonded state consisting of dehydrated isolated charges.[48]

Wool, being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at loftier temperatures tin can permanently pause the hydrogen bonds and a garment may permanently lose its shape.

Cellulose [edit]

Hydrogen bonds are of import in the structure of cellulose and derived polymers in its many unlike forms in nature, such as cotton fiber and flax.

A strand of cellulose (conformation Iα), showing the hydrogen bonds (dashed) within and between cellulose molecules

Constructed polymers [edit]

Many polymers are strengthened past hydrogen bonds within and betwixt the chains. Amidst the constructed polymers, a well characterized example is nylon, where hydrogen bonds occur in the repeat unit of measurement and play a major role in crystallization of the material. The bonds occur between carbonyl and amine groups in the amide repeat unit. They finer link adjacent chains, which help reinforce the textile. The upshot is corking in aramid fibre, where hydrogen bonds stabilize the linear chains laterally. The chain axes are aligned along the fibre axis, making the fibres extremely strong and potent.

The hydrogen-bond networks brand both natural and synthetic polymers sensitive to humidity levels in the atmosphere because water molecules tin can diffuse into the surface and disrupt the network. Some polymers are more sensitive than others. Thus nylons are more sensitive than aramids, and nylon vi more sensitive than nylon-xi.

Symmetric hydrogen bond [edit]

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 instance of a three-centre four-electron bond. This type of bond is much stronger than a "normal" hydrogen bond. The effective bail order is 0.5, so its strength is comparable to a covalent bond. It is seen in ice at loftier pressure, and too in the solid phase of many anhydrous acids such equally hydrofluoric acrid and formic acid at high pressure. It is likewise seen in the bifluoride ion [F--H--F]−. Due to severe steric constraint, the protonated form of Proton Sponge (1,8-bis(dimethylamino)naphthalene) and its derivatives also have symmetric hydrogen bonds ([Due north--H--N]+),[49] although in the instance of protonated Proton Sponge, the assembly is bent.[50]

Dihydrogen bond [edit]

The hydrogen bond tin exist compared with the closely related dihydrogen bond, which is also an intermolecular bonding interaction involving hydrogen atoms. These structures have been known for some fourth dimension, and well characterized past crystallography;[51] all the same, an understanding of their relationship to the conventional hydrogen bond, ionic bond, and covalent bond remains unclear. By and large, the hydrogen bail is characterized by a proton acceptor that is a lone pair of electrons in nonmetallic atoms (most notably in the nitrogen, and chalcogen groups). In some cases, these proton acceptors may be pi-bonds or metallic complexes. In the dihydrogen bond, all the same, a metal hydride serves as a proton acceptor, thus forming a hydrogen-hydrogen interaction. Neutron diffraction has shown that the molecular geometry of these complexes is similar to hydrogen bonds, in that the bond length is very adaptable to the metal complex/hydrogen donor system.[51]

Dynamics probed by spectroscopic ways [edit]

The dynamics of hydrogen bail structures in h2o can be probed by the IR spectrum of OH stretching vibration.[52] In the hydrogen bonding network in protic organic ionic plastic crystals (POIPCs), which are a type of phase change material exhibiting solid-solid stage transitions prior to melting, variable-temperature infrared spectroscopy can reveal the temperature dependence of hydrogen bonds and the dynamics of both the anions and the cations.[53] The sudden weakening of hydrogen bonds during the solid-solid phase transition seems to be coupled with the onset of orientational or rotational disorder of the ions.[53]

Application to drugs [edit]

Hydrogen bonding is a central to the blueprint of drugs. According to Lipinski's rule of five the majority of orally active drugs tend to have betwixt five and ten hydrogen bonds. These interactions be betwixt nitrogen–hydrogen and oxygen–hydrogen centers.[54] As with many other rules of thumb, many exceptions exist.

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Further reading [edit]

  • George A. Jeffrey. An Introduction to Hydrogen Bonding (Topics in Physical Chemistry). Oxford Academy Press, U.s. (March 13, 1997). ISBN 0-19-509549-9

External links [edit]

  • The Bubble Wall (Audio slideshow from the National High Magnetic Field Laboratory explaining cohesion, surface tension and hydrogen bonds)
  • isotopic effect on bail dynamics

schmidtknou1964.blogspot.com

Source: https://en.wikipedia.org/wiki/Hydrogen_bond

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