Hydrogen bond - Knowledge (XXG)

183: 1264: 31: 246: 3828: 199: 386:, sometimes also NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can be taken as indication of the hydrogen bond strength. One scheme gives the following somewhat arbitrary classification: those that are 15 to 40 kcal/mol, 5 to 15 kcal/mol, and >0 to 5 kcal/mol are considered strong, moderate, and weak, respectively. 238: 1272: 3822: 1044: 267:

that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Ac with electronegativity approaching that of hydrogen (rather than being much more electronegative). Although weak (≈1 kcal/mol), "non-traditional" hydrogen bonding interactions are ubiquitous and influence structures of many kinds of materials.

3834: 795:. Owing to the difficulty of breaking these bonds, water has a very high boiling point, melting point, and viscosity compared to otherwise similar liquids not conjoined by hydrogen bonds. Water is unique because its oxygen atom has two lone pairs and two hydrogen atoms, meaning that the total number of bonds of a water molecule is up to four. 744: 736: 599:

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. The sudden weakening of hydrogen bonds during the solid-solid phase transition seems to be coupled with the onset of orientational

225:

In a hydrogen bond, the electronegative atom not covalently attached to the hydrogen is named the proton acceptor, whereas the one covalently bound to the hydrogen is named the proton donor. This nomenclature is recommended by the IUPAC. The hydrogen of the donor is protic and therefore can act as a

772:

and is often used as a model system. When more molecules are present, as is the case with liquid water, more bonds are possible because the oxygen of one water molecule has two lone pairs of electrons, each of which can form a hydrogen bond with a hydrogen on another water molecule. This can repeat

266:

In weaker hydrogen bonds, hydrogen atoms tend to bond to elements such as sulfur (S) or chlorine (Cl); even carbon (C) can serve as a donor, particularly when the carbon or one of its neighbors is electronegative (e.g., in chloroform, aldehydes and terminal acetylenes). Gradually, it was recognized

1213:

Several studies have shown that hydrogen bonds play an important role for the stability between subunits in multimeric proteins. For example, a study of sorbitol dehydrogenase displayed an important hydrogen bonding network which stabilizes the tetrameric quaternary structure within the mammalian

594:

stretching frequency and a decrease in the bond length. H-bonds can also 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 form H-bonds with side-chain hydroxyl groups. The dynamics of hydrogen bond

802:

liquid water simulations at 25 °C, it was estimated that each water molecule participates in an average of 3.59 hydrogen bonds. At 100 °C, this number decreases to 3.24 due to the increased molecular motion and decreased density, while at 0 °C, the average number of hydrogen bonds

1023:

bonds that comprise most polymers, hydrogen bonds are far weaker, perhaps 5%. Thus, hydrogen bonds can be broken 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

815:

A single hydrogen atom can participate in two hydrogen bonds. This type of bonding is called "bifurcated" (split in two or "two-forked"). It can exist, for instance, in complex organic molecules. It has been suggested that a bifurcated hydrogen atom is an essential step in water reorientation.

433:

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:

381:

The strength of intermolecular hydrogen bonds is most often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution. The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without

806:

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 almost always unfavorable

2529:

Luo, Jiangshui; Jensen, Annemette H.; Brooks, Neil R.; Sniekers, Jeroen; Knipper, Martin; Aili, David; Li, Qingfeng; Vanroy, Bram; Wübbenhorst, Michael; Yan, Feng; Van Meervelt, Luc; Shao, Zhigang; Fang, Jianhua; Luo, Zheng-Hong; De Vos, Dirk E.; Binnemans, Koen; Fransaer, Jan (2015).

3413:

Ozeryanskii, Valery A.; Pozharskii, Alexander F.; Bieńko, Agnieszka J.; Sawka-Dobrowolska, Wanda; Sobczyk, Lucjan (2005-03-01). "+ Hydrogen Bonding in Protonated 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene. X-ray Diffraction, Infrared, and Theoretical ab Initio and DFT Studies".

2022:

Arunan, Elangannan; Desiraju, Gautam R.; Klein, Roger A.; Sadlej, Joanna; Scheiner, Steve; Alkorta, Ibon; Clary, David C.; Crabtree, Robert H.; Dannenberg, Joseph J.; Hobza, Pavel; Kjaergaard, Henrik G.; Legon, Anthony C.; Mennucci, Benedetta; Nesbitt, David J. (2011).

149:

The hydrogen bond is also responsible for many of the physical and chemical properties of compounds of N, O, and F that seem unusual compared with other similar structures. In particular, intermolecular hydrogen bonding is responsible for the high boiling point of

122:(occurring among parts of the same molecule). The energy of a hydrogen bond depends on the geometry, the environment, and the nature of the specific donor and acceptor atoms and can vary between 1 and 40 kcal/mol. This makes them somewhat stronger than a 1354:. This type of bond is much stronger than a "normal" hydrogen bond. The effective bond order is 0.5, so its strength is comparable to a covalent bond. It is seen in ice at high pressure, and also in the solid phase of many anhydrous acids such as 3399:

Khashayar Rajabimoghadam Yousef Darwish Umyeena Bashir Dylan Pitman Sidney Eichelberger Maxime A. Siegler Marcel Swart Isaac Garcia-Bosch Aerobic Oxidation of Alcohols by Copper Complexes Bearing Redox-Active Ligands with Tunable H-Bonding

1179:. The energy preference of the bifurcated H-bond hydroxyl or thiol system is -3.4 kcal/mol or -2.6 kcal/mol, respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-chains, such as 42: 1063:

In these macromolecules, bonding between parts of the same macromolecule cause it to fold into a specific shape, which helps determine the molecule's physiological or biochemical role. For example, the double helical structure of

819:

Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (it is called overcoordinated oxygen, OCO) than are donor-type hydrogen bonds, beginning on the same oxygen's hydrogens.

1255:, being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at high temperatures can permanently break the hydrogen bonds and a garment may permanently lose its shape. 2907: 1206:(CD) experiments have shown osmolyte to act through an enthalpic effect. The molecular mechanism for their role in protein stabilization is still not well established, though several mechanisms have been proposed. Computer 1202:, shift the protein folding equilibrium toward the folded state, in a concentration dependent manner. While the prevalent explanation for osmolyte action relies on excluded volume effects that are entropic in nature, 595:

structures in water can be probed by this OH stretching vibration. In the hydrogen bonding network in protic organic ionic plastic crystals (POIPCs), which are a type of phase change material exhibiting solid-solid

1318:, where hydrogen bonds stabilize the linear chains laterally. The chain axes are aligned along the fibre axis, making the fibres extremely stiff and strong. Hydrogen-bond networks make both polymers sensitive to 714:

credits T. S. Moore and T. F. Winmill with the first mention of the hydrogen bond, in 1912. Moore and Winmill used the hydrogen bond to account for the fact that trimethylammonium hydroxide is a weaker base than

773:

such that every water molecule is H-bonded with up to four other molecules, as shown in the figure (two through its two lone pairs, and two through its two hydrogen atoms). Hydrogen bonding strongly affects the

781:, 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 most other substances. 807:

relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes. Hydrogen bonds between water molecules have an average lifetime of 10 seconds, or 10 picoseconds.

3471:; Siegbahn, Per E. M.; Eisenstein, Odile; Rheingold, Arnold L.; Koetzle, Thomas F. (1996). "A New Intermolecular Interaction: Unconventional Hydrogen Bonds with Element-Hydride Bonds as Proton Acceptor". 1350:

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

727:, saying, "Mr. Huggins of this laboratory in some work as yet unpublished, has used the idea of a hydrogen kernel held between two atoms as a theory in regard to certain organic compounds." 259:

Hydrogen bonds arise from a combination of electrostatics (multipole-multipole and multipole-induced multipole interactions), covalency (charge transfer by orbital overlap), and dispersion (

1523:

Hapala, Prokop; Kichin, Georgy; Wagner, Christian; Tautz, F. Stefan; Temirov, Ruslan; Jelínek, Pavel (2014-08-19). "Mechanism of high-resolution STM/AFM imaging with functionalized tips".

2331:

Legon, A. C.; Millen, D. J. (1987). "Angular geometries and other properties of hydrogen-bonded dimers: a simple electrostatic interpretation of the success of the electron-pair model".

3072:"Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto \2,3-f] quinoxalinedione-7,12 obtenue" 907: 1714:

Arunan, Elangannan; Desiraju, Gautam R.; Klein, Roger A.; Sadlej, Joanna; Scheiner, Steve; Alkorta, Ibon; Clary, David C.; Crabtree, Robert H.; Dannenberg, Joseph J. (2011-07-08).

52:

molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77 K. ("Hydrogen bonds" in the top image are exaggerated by artifacts of the imaging technique.)

2524: 2522: 575: 401:(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 803:

increases to 3.69. Another study found a much smaller number of hydrogen bonds: 2.357 at 25 °C. Defining and counting the hydrogen bonds is not straightforward however.

1826: 3921: 1578:"Binding and Release between Polymeric Carrier and Protein Drug: pH-Mediated Interplay of Coulomb Forces, Hydrogen Bonding, van der Waals Interactions, and Entropy" 1370:. Due to severe steric constraint, the protonated form of Proton Sponge (1,8-bis(dimethylamino)naphthalene) and its derivatives also have symmetric hydrogen bonds ( 1919:

Beijer, Felix H.; Kooijman, Huub; Spek, Anthony L.; Sijbesma, Rint P.; Meijer, E. W. (1998). "Self-Complementarity Achieved through Quadruple Hydrogen Bonding".

1402:

remains unclear. Generally, the hydrogen bond is characterized by a proton acceptor that is a lone pair of electrons in nonmetallic atoms (most notably in the

1438:

the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between

702:

demonstrated information transfer between hydrogen-bonded nuclei, a feat that would only be possible if the hydrogen bond contained some covalent character.

3614: 1322:

levels in the atmosphere because water molecules can diffuse into the surface and disrupt the network. Some polymers are more sensitive than others. Thus

288:

in which X is more electronegative than H, and an atom or a group of atoms in the same or another molecule, in which there is evidence of bond formation.

2693:

Ghanty, Tapan K.; Staroverov, Viktor N.; Koren, Patrick R.; Davidson, Ernest R. (2000-02-01). "Is the Hydrogen Bond in Water Dimer and Ice Covalent?".

2067:"Gas-phase bihalide and pseudobihalide ions. An ion cyclotron resonance determination of hydrogen bond energies in XHY- species (X, Y = F, Cl, Br, CN)" 2288:

Lin, Xuhui; Zhang, Huaiyu; Jiang, Xiaoyu; Wu, Wei; Mo, Yirong (2017). "The Origin of the Non-Additivity in Resonance-Assisted Hydrogen Bond Systems".

1011:

Hydrogen bonding plays an important role in determining the three-dimensional structures and the properties adopted by many proteins. Compared to the

1466:

Sweetman, A. M.; Jarvis, S. P.; Sang, Hongqian; Lekkas, I.; Rahe, P.; Wang, Yu; Wang, Jianbo; Champness, N.R.; Kantorovich, L.; Moriarty, P. (2014).

4039: 3966: 3647: 2532:"1,2,4-Triazolium perfluorobutanesulfonate as an archetypal pure protic organic ionic plastic crystal electrolyte for all-solid-state fuel cells" 3054: 2833: 2607: 2362: 3249:

Gilman-Politi, Regina; Harries, Daniel (2011). "Unraveling the Molecular Mechanism of Enthalpy Driven Peptide Folding by Polyol Osmolytes".

1933: 1194:

The role of hydrogen bonds in protein folding has also been linked to osmolyte-induced protein stabilization. Protective osmolytes, such as

2471:

Cowan ML; Bruner BD; Huse N; et al. (2005). "Ultrafast memory loss and energy redistribution in the hydrogen bond network of liquid H

2151: 3286:"A hydrogen-bonding network in mammalian sorbitol dehydrogenase stabilizes the tetrameric state and is essential for the catalytic power" 45: 2623:

Grunenberg, Jörg (2004). "Direct Assessment of Interresidue Forces in Watson−Crick Base Pairs Using Theoretical Compliance Constants".

1625:

Hämäläinen, Sampsa K.; van der Heijden, Nadine; van der Lit, Joost; den Hartog, Stephan; Liljeroth, Peter; Swart, Ingmar (2014-10-31).

1426:

of these complexes is similar to hydrogen bonds, in that the bond length is very adaptable to the metal complex/hydrogen donor system.

1033: 405:

model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between

49: 4075: 3602: 1946:

Desiraju, G. R. and Steiner, T. The Weak Hydrogen Bond: In Structural Chemistry and Biology, International Union of Crystallography;

2728:

Cordier, F; Rogowski, M; Grzesiek, S; Bax, A (1999). "Observation of through-hydrogen-bond (2h)J(HC') in a perdeuterated protein".

2536: 2261:

Gu, Yanliang; Kar, Tapas; Scheiner, Steve (1999). "Fundamental Properties of the CH···O Interaction: Is It a True Hydrogen Bond?".

3901: 270:

The definition of hydrogen bonding has gradually broadened over time to include these weaker attractive interactions. In 2011, an

3886: 1626: 3710: 1351: 639: 3737: 1870: 1418:. In the dihydrogen bond, however, a metal hydride serves as a proton acceptor, thus forming a hydrogen-hydrogen interaction. 182: 4080: 3698: 3688: 1975: 1955: 1815: 1791: 1771: 1283:

The properties of many polymers are affected by hydrogen bonds within and/or between the chains. Prominent examples include

748: 2820:

The nature of the chemical bond and the structure of molecules and crystals; an introduction to modern structural chemistry

764:

molecules. In a discrete water molecule, there are two hydrogen atoms and one oxygen atom. The simplest case is a pair of

3693: 3617:(Audio slideshow from the National High Magnetic Field Laboratory explaining cohesion, surface tension and hydrogen bonds) 2971:

Zielkiewicz, Jan (2005). "Structural properties of water: Comparison of the SPC, SPCE, TIP4P, and TIP5P models of water".

716: 3640: 1390:

bonding interaction involving hydrogen atoms. These structures have been known for some time, and well characterized by

1134:

is formed. When two strands are joined by hydrogen bonds involving alternating residues on each participating strand, a

274:

Task Group recommended a modern evidence-based definition of hydrogen bonding, which was published in the IUPAC journal

2935:

Jorgensen, W. L.; Madura, J. D. (1985). "Temperature and size dependence for Monte Carlo simulations of TIP4P water".

2571:

Weinhold, Frank; Klein, Roger A. (2014). "What is a hydrogen bond? Resonance covalency in the supramolecular domain".

2148:

as detailed in the reference and should be compared to 7.9 kJ/mol for bulk water, obtained using the same calculation.

1210:

simulations suggest that osmolytes stabilize proteins by modifying the hydrogen bonds in the protein hydration layer.

1089: 586:

stretching frequency to lower energy (i.e. the vibration frequency decreases). This shift reflects a weakening of the

230:

system, where the dots represent the hydrogen bond. Liquids that display hydrogen bonding (such as water) are called

3156:

Markovitch, Omer; Agmon, Noam (2008). "The Distribution of Acceptor and Donor Hydrogen-Bonds in Bulk Liquid Water".

382:

hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is

1435: 1139: 699: 276: 3961: 3956: 698:

suggested that the hydrogen bonds had a partial covalent nature. This interpretation remained controversial until

4070: 4065: 3946: 3936: 3911: 3881: 643: 146:

together, and for causing separate sheets of paper to stick together after becoming wet and subsequently drying.

3070:

Baron, Michel; Giorgi-Renault, Sylviane; Renault, Jean; Mailliet, Patrick; Carré, Daniel; Etienne, Jean (1984).

627:) revealed large differences between individual H bonds of the same type. For example, the central interresidue 96:, and the dotted or dashed line indicates the hydrogen bond. The most frequent donor and acceptor atoms are the 3727: 2101: 1311:

effectively link adjacent chains, which gives the material mechanical strength. Hydrogen bonds also affect the

798:

The number of hydrogen bonds formed by a molecule of liquid water fluctuates with time and temperature. From

720: 719:. The description of hydrogen bonding in its better-known setting, water, came some years later, in 1920, from 284:

The hydrogen bond is an attractive interaction between a hydrogen atom from a molecule or a molecular fragment

3214:

Politi, Regina; Harries, Daniel (2010). "Enthalpically driven peptide stabilization by protective osmolytes".

657:

of ordinary ice claim that the hydrogen bond is partly covalent. However, this interpretation was challenged.

2531: 940:

The fact that ice is less dense than liquid water is due to a crystal structure stabilized by hydrogen bonds.

3988: 3891: 3863: 3633: 3620: 2066: 1347: 842: 723:

and Rodebush. In that paper, Latimer and Rodebush cited the work of a fellow scientist at their laboratory,

541: 260: 191: 2176: 1242: 1153: 4032: 3993: 1921: 1858: 1391: 724: 553: 155: 4027: 2658:

Isaacs, E.D.; et al. (1999). "Covalency of the Hydrogen Bond in Ice: A Direct X-Ray Measurement".

1149: 1263: 3951: 3842: 3705: 3664: 3423: 3354: 3165: 3114: 2981: 2945: 2790: 2739: 2667: 2484: 2425: 2297: 2168: 1648: 1542: 1479: 1387: 672: 661: 624: 202: 119: 3015:

Jencks, William; Jencks, William P. (1986). "Hydrogen Bonding between Solutes in Aqueous Solution".

2226:

Biedermann F, Schneider HJ (May 2016). "Experimental Binding Energies in Supramolecular Complexes".

297:

Hydrogen bonds can vary in strength from weak (1–2 kJ/mol) to strong (161.5 kJ/mol in the

158:

that have much weaker hydrogen bonds. Intramolecular hydrogen bonding is partly responsible for the

30: 3853: 3717: 3683: 2181: 1419: 159: 123: 35: 4017: 245: 3772: 3468: 3323: 3181: 3138: 2763: 2553: 2508: 2357:

Friebolin, H., "Basic One- and Two- Dimensional NMR Spectroscopy, 4th ed.," VCH: Weinheim, 2008.

2145: 2047: 1745: 1680: 1638: 1558: 1532: 1423: 1207: 1203: 691: 654: 163: 4003: 3792: 3752: 3742: 3598: 3573: 3524: 3489: 3447: 3439: 3382: 3315: 3266: 3231: 3130: 3105: 3050: 3017: 2997: 2829: 2825: 2755: 2710: 2640: 2603: 2500: 2453: 2391: 2358: 2313: 2243: 2194: 2004: 1971: 1951: 1874: 1811: 1787: 1767: 1737: 1672: 1607: 1505: 1355: 992: 829: 774: 135: 97: 88:

of electrons—the hydrogen bond acceptor (Ac). Such an interacting system is generally denoted

81: 3103:

Laage, Damien; Hynes, James T. (2006). "A Molecular Jump Mechanism for Water Reorientation".

2202: 4044: 3827: 3784: 3757: 3563: 3555: 3516: 3481: 3431: 3372: 3362: 3305: 3297: 3258: 3223: 3173: 3122: 3083: 3025: 2989: 2953: 2889: 2858: 2798: 2747: 2702: 2675: 2632: 2580: 2545: 2492: 2443: 2433: 2383: 2340: 2305: 2270: 2235: 2186: 2159: 2110: 2078: 2037: 2029: 1996: 1929: 1901: 1866: 1840: 1727: 1664: 1656: 1597: 1589: 1550: 1495: 1487: 1246: 1238: 596: 3507:

Lipinski CA (December 2004). "Lead- and drug-like compounds: the rule-of-five revolution".

198: 3896: 3767: 3473: 1415: 1383: 1143: 1077: 988: 977: 608:

Hydrogen bonding is of persistent theoretical interest. According to a modern description

383: 241:

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

4022: 3427: 3358: 3310: 3285: 3169: 3118: 2985: 2949: 2794: 2743: 2671: 2488: 2429: 2301: 2172: 1652: 1627:"Intermolecular Contrast in Atomic Force Microscopy Images without Intermolecular Bonds" 1546: 1483: 832:—which has three lone pairs on the F atom but only one H atom—can form only two bonds; ( 791:

is due to the high number of hydrogen bonds each molecule can form, relative to its low

638:

Theoretically, the bond strength of the hydrogen bonds can be assessed using NCI index,

3931: 3732: 3568: 3543: 2973: 2448: 2413: 1500: 1467: 1403: 792: 187: 115: 69: 3377: 3342: 1688: 930:, and viscosity of many compounds can be explained by the concept of hydrogen bonding. 4059: 3980: 3940: 3802: 3675: 3656: 2818: 1892:

Sabin, John R. (1971). "Hydrogen bonds involving sulfur. I. Hydrogen sulfide dimer".

1399: 1394:; however, an understanding of their relationship to the conventional hydrogen bond, 1226: 1024:

stronger than van der Waals forces) is relevant in the properties of many materials.

996: 923: 919: 788: 711: 695: 679: 665: 545: 402: 206: 127: 93: 77: 3327: 3185: 2557: 2051: 1836: 1749: 1562: 612:

integrates both the intermolecular O:H lone pair ":" nonbond and the intramolecular

138:

like DNA and proteins. Hydrogen bonds are responsible for holding materials such as

3926: 3142: 2730: 2512: 1684: 1660: 1037: 675: 668: 171: 2781:

Needham, Paul (2013). "Hydrogen bonding: Homing in on a tricky chemical concept".

2767: 590:

bond. Certain hydrogen bonds - improper hydrogen bonds - show a blue shift of the

3284:

Hellgren, M.; Kaiser, C.; de Haij, S.; Norberg, A.; Höög, J. O. (December 2007).

3044: 1602: 1241:. Furthermore, the dehydration stabilizes the hydrogen bond by destabilizing the 631:

hydrogen bond between guanine and cytosine is much stronger in comparison to the

226:

Lewis acid and the acceptor is the Lewis base. Hydrogen bonds are represented as

4012: 3762: 3520: 2849:

Moore, T. S.; Winmill, T. F. (1912). "The state of amines in aqueous solution".

2802: 2239: 1831: 1359: 1112: 1073: 799: 769: 687: 623:

Quantum chemical calculations of the relevant interresidue potential constants (

17: 3821: 2679: 1593: 1554: 1271: 347:(21 kJ/mol or 5.0 kcal/mol), illustrated water-water, alcohol-alcohol 237: 3559: 3544:"A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs" 3301: 3177: 2957: 2937: 1395: 1363: 1217:

A protein backbone hydrogen bond incompletely shielded from water attack is a

1135: 1127: 1097: 927: 683: 671:

between two or more intermolecular bonds. This is slightly different from the

650: 298: 131: 3443: 2714: 2309: 2042: 2024: 1934:

10.1002/(SICI)1521-3773(19980202)37:1/2<75::AID-ANIE75>3.0.CO;2-R

1835:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) " 1741: 1732: 1715: 1577: 1279:), showing the hydrogen bonds (dashed) within and between cellulose molecules 1100:

residues participating in a hydrogen bond occurs regularly between positions

739:

Crystal structure of hexagonal ice. Gray dashed lines indicate hydrogen bonds

3747: 3722: 3367: 3126: 2878:"Polarity and ionization from the standpoint of the Lewis theory of valence" 2438: 1844: 1407: 1284: 1195: 1184: 1069: 1056: 995:, which occur even in the gas phase, resulting in gross deviations from the 934: 579: 15.5, which is about 10 ppm downfield of a conventional alcohol. 426: 85: 57: 3577: 3528: 3493: 3451: 3386: 3319: 3270: 3235: 3134: 3001: 2759: 2751: 2644: 2504: 2457: 2395: 2317: 2247: 2198: 2008: 1878: 1676: 1611: 1509: 1374:), although in the case of protonated Proton Sponge, the assembly is bent. 1076:

interactions), which link one complementary strand to the other and enable

1032: 694:

has a net negative sum. The initial theory of hydrogen bonding proposed by

1043: 134:. This type of bond can occur in inorganic molecules such as water and in 2862: 2344: 2114: 1443: 1439: 1335: 1319: 1300: 1234: 1218: 1199: 1188: 1052: 981: 314: 213: 108: 100: 73: 3542:

o′Hagan, Steve; Swainston, Neil; Handl, Julia; Kell, Douglas B. (2015).

3029: 2893: 2496: 2082: 1905: 836:

has the opposite problem: three hydrogen atoms but only one lone pair).

41: 3401: 3227: 2584: 2549: 2000: 1668: 1491: 1411: 1331: 1048: 833: 167: 84:"donor" atom or group (Dn), and another electronegative atom bearing a 27:

Intermolecular attraction between a hydrogen-donor pair and an acceptor

3485: 3435: 3262: 2993: 2706: 2636: 2387: 2274: 2190: 1576:

De Luca, S.; Chen, F.; Seal, P.; Stenzel, M. H.; Smith, S. C. (2017).

3341:

Fernández, A.; Rogale K.; Scott Ridgway; Scheraga H. A. (June 2004).

1871:

10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U

1447: 1327: 1312: 1288: 1222: 1180: 784: 353:(13 kJ/mol or 3.1 kcal/mol), illustrated by ammonia-ammonia 104: 3088: 3071: 2877: 743: 3833: 1450:–hydrogen centers. Many drugs do not, however, obey these "rules". 768:

molecules with one hydrogen bond between them, which is called the

735: 646:, as its name indicates, using the electron density of the system. 324:(161.5 kJ/mol or 38.6 kcal/mol), illustrated uniquely by 3595:

An Introduction to Hydrogen Bonding (Topics in Physical Chemistry)

1643: 1537: 1323: 1315: 1304: 1296: 1270: 1230: 1093: 1042: 1031: 765: 761: 742: 734: 271: 194:

dimer complex. The hydrogen bonds are represented by dotted lines.

151: 139: 40: 29: 3625: 3343:"Inhibitor design by wrapping packing defects in HIV-1 proteins" 1987:

Nishio, M (2011). "The CH/ hydrogen bond in chemistry. "Title".

1856:

Steiner, Thomas (2002). "The Hydrogen Bond in the Solid State".

1292: 1252: 389:

Hydrogen bonds involving C-H bonds are both very rare and weak.

341:(29 kJ/mol or 6.9 kcal/mol), illustrated water-ammonia 210: 143: 3629: 2824:(3rd ed.). Ithaca (NY): Cornell University Press. p. 1716:"Definition of the hydrogen bond (IUPAC Recommendations 2011)" 1065: 778: 540:

Strong hydrogen bonds are revealed by downfield shifts in the

1221:. Dehydrons promote the removal of water through proteins or 359:(8 kJ/mol or 1.9 kcal/mol), illustrated water-amide 2152:"Structure and energetics of the hydronium hydration shells" 1002:

Pentamer formation of water and alcohols in apolar solvents.

1434:

The Hydrogen bond is relevant to drug design. According to

1382:

The hydrogen bond can be compared with the closely related

2407: 2405: 2374:

Hobza P, Havlas Z (2000). "Blue-Shifting Hydrogen Bonds".

1164:

as the H-bond acceptor and two H-bond donors from residue

1138:

is formed. Hydrogen bonds also play a part in forming the

760:

An ubiquitous example of a hydrogen bond is found between

544:. For example, the acidic proton in the enol tautomer of 2131:(Eds.: E. Grushka, N. Grinberg), CRC Press, Boca Raton, 1468:"Mapping the force field of a hydrogen-bonded assembly" 1115:

is formed. When the spacing is less, between positions

1092:, hydrogen bonds form between the backbone oxygens and 811:

Bifurcated and over-coordinated hydrogen bonds in water

1410:

groups). In some cases, these proton acceptors may be

710:

The concept of hydrogen bonding once was challenging.

2600:

The Attribute of Water: Single Notion, Multiple Myths

845: 660:

Most generally, the hydrogen bond can be viewed as a

556: 4002: 3979: 3910: 3872: 3852: 3841: 3801: 3783: 3674: 3663: 2783:

Studies in History and Philosophy of Science Part A

2817: 913:Further manifestations of solvent hydrogen bonding 901: 569: 2099:Emsley, J. (1980). "Very Strong Hydrogen Bonds". 1970:; Wiley-VCH, New York, 1998. • Wiley-VCH; 1998) 686:. However, hydrogen bonding is generally still a 34:Model of hydrogen bonds (1) between molecules of 3597:. Oxford University Press, US (March 13, 1997). 2930: 2928: 2876:Latimer, Wendell M.; Rodebush, Worth H. (1920). 582:In the IR spectrum, hydrogen bonding shifts the 3347:Proceedings of the National Academy of Sciences 2418:Proceedings of the National Academy of Sciences 1068:is due largely to hydrogen bonding between its 282: 2412:Feldblum, Esther S.; Arkin, Isaiah T. (2014). 1191:within the hydrophobic membrane environments. 3641: 1372:[N···H···N] 1368:[F···H···F] 8: 973:, and HCl, where hydrogen-bonding is absent. 2127:V. David, N. Grinberg, S. C. Moldoveanu in 1142:through interaction of R-groups. (See also 958:, and HF compared to the heavier analogues 751:, which features two linear hydrogen-bonds. 3849: 3671: 3648: 3634: 3626: 3251:Journal of Chemical Theory and Computation 3049:. Cambridge University Press. p. 37. 2908:"11.9: Water - An Extraordinary Substance" 1786:; Oxford university press New York, 1997. 118:(occurring between separate molecules) or 3567: 3376: 3366: 3309: 3087: 2573:Chemistry Education Research and Practice 2447: 2437: 2180: 2094: 2092: 2041: 1804:Hydrogen bonding in biological structures 1731: 1642: 1601: 1536: 1499: 1362:at high pressure. It is also seen in the 1225:. The exogenous dehydration enhances the 890: 870: 850: 846: 844: 561: 555: 4040:Polyhedral skeletal electron pair theory 2882:Journal of the American Chemical Society 2695:Journal of the American Chemical Society 2625:Journal of the American Chemical Society 2263:Journal of the American Chemical Society 1262: 968: 961: 953: 946: 642:, which allows a visualization of these 519: 502: 485: 468: 436: 373: 244: 236: 197: 181: 3463: 3461: 1458: 1214:sorbitol dehydrogenase protein family. 902:{\displaystyle {\ce {H-F***H-F***H-F}}} 635:bond between the adenine-thymine pair. 221:Definitions and general characteristics 92:, where the solid line denotes a polar 2150:Markovitch, Omer; Agmon, Noam (2007). 2065:Larson, J. W.; McMahon, T. B. (1984). 943:Dramatically higher boiling points of 3201:Hydrogen Bonding in Polymer Materials 1275:A strand of cellulose (conformation I 377:(18 kJ/mol or 4.3 kcal/mol) 7: 3402:https://doi.org/10.1021/jacs.8b08748 3290:Cellular and Molecular Life Sciences 3046:Biophysics: A Physiological Approach 2129:Advances in Chromatography Volume 54 1966:Nishio, M.; Hirota, M.; Umezawa, Y. 1709: 1707: 1705: 1152:systems are common in alpha-helical 616:polar-covalent bond associated with 600:or rotational disorder of the ions. 249:Cyclic dimer of acetic acid; dashed 154:(100 °C) compared to the other 3416:The Journal of Physical Chemistry A 2290:The Journal of Physical Chemistry A 1784:An introduction to hydrogen bonding 1175:and a side-chain hydroxyl or thiol 1096:hydrogens. When the spacing of the 3509:Drug Discovery Today: Technologies 2537:Energy & Environmental Science 1832:Compendium of Chemical Terminology 570:{\displaystyle \delta _{\text{H}}} 50:naphthalenetetracarboxylic diimide 25: 2414:"Strength of a bifurcated H bond" 2025:"Definition of the hydrogen bond" 731:Hydrogen bonds in small molecules 3832: 3826: 3820: 3621:isotopic effect on bond dynamics 1287:and its derived fibers, such as 425:distance is typically ≈110 399:resonance assisted hydrogen bond 393:Resonance assisted hydrogen bond 1352:three-center four-electron bond 1090:secondary structure of proteins 1036:The structure of part of a DNA 640:non-covalent interactions index 1661:10.1103/PhysRevLett.113.186102 749:nickel bis(dimethylglyoximate) 255:lines represent hydrogen bonds 72:force of attraction between a 1: 1237:groups by de-shielding their 1140:tertiary structure of protein 717:tetramethylammonium hydroxide 280:. This definition specifies: 2598:Sun, C. Q.; Sun, Yi (2016). 1802:Jeffrey, G. A.; Saenger, W. 937:of mixtures of HF and water. 411:···O=C−C=C−OH 3521:10.1016/j.ddtec.2004.11.007 2803:10.1016/j.shpsa.2012.04.001 2240:10.1021/acs.chemrev.5b00583 1156:between the backbone amide 4097: 3738:Metal–ligand multiple bond 2680:10.1103/PhysRevLett.82.600 1766:Franklin Classics, 2018), 1720:Pure and Applied Chemistry 1594:10.1021/acs.biomac.7b00657 1555:10.1103/PhysRevB.90.085421 1007:Hydrogen bonds in polymers 604:Theoretical considerations 277:Pure and Applied Chemistry 3818: 3560:10.1007/s11306-014-0733-z 3302:10.1007/s00018-007-7318-1 3178:10.1080/00268970701877921 2958:10.1080/00268978500103111 1299:, hydrogen bonds between 1245:consisting of dehydrated 1047:Hydrogen bonding between 991:and hexamer formation in 644:non-covalent interactions 124:van der Waals interaction 4076:Supramolecular chemistry 2333:Chemical Society Reviews 2310:10.1021/acs.jpca.7b09425 2102:Chemical Society Reviews 2043:10.1351/PAC-REC-10-01-02 1733:10.1351/PAC-REC-10-01-02 1326:are more sensitive than 1229:interaction between the 407:O=C−OH··· 126:, and weaker than fully 90:Dn−H···Ac 3368:10.1073/pnas.0404641101 3127:10.1126/science.1122154 2660:Physical Review Letters 2439:10.1073/pnas.1319827111 1845:10.1351/goldbook.H02899 1631:Physical Review Letters 1436:Lipinski's rule of five 1348:symmetric hydrogen bond 1342:Symmetric hydrogen bond 976:Viscosity of anhydrous 649:Interpretations of the 454:HCN···HF 357:N−H···:O 351:N−H···:N 345:O−H···:O 339:O−H···:N 322:F−H···:F 3199:Shiao-Wei Kuo (2018). 3043:Dillon, P. F. (2012). 2752:10.1006/jmre.1999.1899 1989:Phys. Chem. Chem. Phys 1280: 1268: 1154:transmembrane proteins 1060: 1055:, one of two types of 1040: 903: 752: 740: 690:phenomenon, since the 633:N−H···N 629:N−H···N 571: 471:CO···HF 290: 256: 242: 217: 195: 190:hydrogen bonding in a 114:Hydrogen bonds can be 53: 38: 4081:Intermolecular forces 1968:The CH–π Interactions 1922:Angew. Chem. Int. Ed. 1859:Angew. Chem. Int. Ed. 1603:1959.4/unsworks_55160 1472:Nature Communications 1274: 1267:Para-aramid structure 1266: 1171:: the backbone amide 1046: 1035: 904: 746: 738: 725:Maurice Loyal Huggins 572: 505:S···HF 488:O···HF 372:···:OH 248: 240: 201: 185: 44: 33: 3728:Coordinate (dipolar) 2912:Chemistry LibreTexts 2863:10.1039/CT9120101635 2816:Pauling, L. (1960). 2345:10.1039/CS9871600467 2144:Data obtained using 2115:10.1039/cs9800900091 1806:; Springer: Berlin, 1430:Application to drugs 1334:more sensitive than 843: 625:compliance constants 620:repulsive coupling. 554: 522:···HF 431:H···Y 228:H···Y 209:helps stabilize the 205:hydrogen bonding in 3902:C–H···O interaction 3684:Electron deficiency 3593:George A. Jeffrey. 3469:Crabtree, Robert H. 3428:2005JPCA..109.1637O 3359:2004PNAS..10111640F 3170:2008MolPh.106..485M 3119:2006Sci...311..832L 3030:10.1021/ja00274a058 2986:2005JChPh.123j4501Z 2950:1985MolPh..56.1381J 2894:10.1021/ja01452a015 2795:2013SHPSA..44...51N 2744:1999JMagR.140..510C 2672:1999PhRvL..82..600I 2497:10.1038/nature03383 2489:2005Natur.434..199C 2430:2014PNAS..111.4085F 2302:2017JPCA..121.8535L 2173:2007JPCA..111.2253M 2083:10.1021/ic00182a010 2071:Inorganic Chemistry 1995:(31): 13873–13900. 1906:10.1021/ja00744a012 1653:2014PhRvL.113r6102H 1547:2014PhRvB..90h5421H 1484:2014NatCo...5.3931S 1422:has shown that the 1420:Neutron diffraction 1386:, which is also an 987:Dimer formation in 3887:Resonance-assisted 3228:10.1039/C0CC01763A 2585:10.1039/c4rp00030g 2550:10.1039/C4EE02280G 2146:molecular dynamics 2001:10.1039/c1cp20404a 1492:10.1038/ncomms4931 1424:molecular geometry 1281: 1269: 1208:molecular dynamics 1204:circular dichroism 1061: 1041: 899: 753: 741: 692:interaction energy 567: 417:Structural details 317:in vapor include: 257: 243: 232:associated liquids 218: 196: 76:(H) atom which is 68:) is primarily an 54: 39: 4053: 4052: 4004:Electron counting 3975: 3974: 3864:London dispersion 3816: 3815: 3793:Metal aromaticity 3486:10.1021/ar950150s 3436:10.1021/jp040618l 3263:10.1021/ct200455n 3257:(11): 3816–3828. 3222:(35): 6449–6451. 3158:Molecular Physics 3056:978-1-139-50462-1 3018:J. Am. Chem. Soc. 2994:10.1063/1.2018637 2835:978-0-8014-0333-0 2707:10.1021/ja9937019 2637:10.1021/ja046282a 2609:978-981-10-0178-9 2483:(7030): 199–202. 2424:(11): 4085–4090. 2388:10.1021/cr990050q 2382:(11): 4253–4264. 2363:978-3-527-31233-7 2296:(44): 8535–8541. 2275:10.1021/ja991795g 2269:(40): 9411–9422. 2191:10.1021/jp068960g 2167:(12): 2253–2256. 2077:(14): 2029–2033. 1900:(15): 3613–3620. 1764:The Hydrogen Bond 1588:(11): 3665–3677. 1582:Biomacromolecules 1525:Physical Review B 1356:hydrofluoric acid 1150:Bifurcated H-bond 993:hydrogen fluoride 897: 889: 877: 869: 857: 849: 830:hydrogen fluoride 775:crystal structure 678:of, for example, 597:phase transitions 564: 533: 532: 156:group-16 hydrides 136:organic molecules 98:period 2 elements 78:covalently bonded 16:(Redirected from 4088: 4071:Hydrogen physics 4066:Chemical bonding 4045:Jemmis mno rules 3897:Dihydrogen bonds 3850: 3836: 3830: 3824: 3758:Hyperconjugation 3672: 3650: 3643: 3636: 3627: 3582: 3581: 3571: 3539: 3533: 3532: 3504: 3498: 3497: 3465: 3456: 3455: 3422:(8): 1637–1642. 3410: 3404: 3397: 3391: 3390: 3380: 3370: 3338: 3332: 3331: 3313: 3281: 3275: 3274: 3246: 3240: 3239: 3211: 3205: 3204: 3196: 3190: 3189: 3153: 3147: 3146: 3100: 3094: 3093: 3091: 3067: 3061: 3060: 3040: 3034: 3033: 3012: 3006: 3005: 2968: 2962: 2961: 2932: 2923: 2922: 2920: 2919: 2904: 2898: 2897: 2888:(7): 1419–1433. 2873: 2867: 2866: 2846: 2840: 2839: 2823: 2813: 2807: 2806: 2778: 2772: 2771: 2725: 2719: 2718: 2701:(6): 1210–1214. 2690: 2684: 2683: 2655: 2649: 2648: 2620: 2614: 2613: 2595: 2589: 2588: 2568: 2562: 2561: 2526: 2517: 2516: 2468: 2462: 2461: 2451: 2441: 2409: 2400: 2399: 2371: 2365: 2355: 2349: 2348: 2328: 2322: 2321: 2285: 2279: 2278: 2258: 2252: 2251: 2228:Chemical Reviews 2223: 2217: 2216: 2214: 2213: 2207: 2201:. Archived from 2184: 2160:J. Phys. Chem. A 2156: 2142: 2136: 2125: 2119: 2118: 2096: 2087: 2086: 2062: 2056: 2055: 2045: 2036:(8): 1637–1641. 2030:Pure Appl. Chem. 2019: 2013: 2012: 1984: 1978: 1964: 1958: 1944: 1938: 1937: 1916: 1910: 1909: 1894:J. Am. Chem. Soc 1889: 1883: 1882: 1853: 1847: 1824: 1818: 1800: 1794: 1782:Jeffrey, G. A.; 1780: 1774: 1760: 1754: 1753: 1735: 1726:(8): 1637–1641. 1711: 1700: 1699: 1697: 1696: 1687:. Archived from 1646: 1622: 1616: 1615: 1605: 1573: 1567: 1566: 1540: 1520: 1514: 1513: 1503: 1463: 1373: 1369: 1247:isolated charges 1178: 1174: 1170: 1159: 1125: 1110: 1022: 1018: 1014: 989:carboxylic acids 972: 964: 957: 949: 918:Increase in the 908: 906: 905: 900: 898: 895: 894: 887: 875: 874: 867: 855: 854: 847: 634: 630: 619: 615: 611: 593: 589: 585: 578: 576: 574: 573: 568: 566: 565: 562: 523: 506: 489: 472: 455: 442: 441:Acceptor···donor 437: 432: 424: 412: 408: 376: 371: 370: 367: 358: 352: 346: 340: 335: 334: 333: 330: 323: 312: 311: 310: 307: 287: 254: 229: 91: 21: 18:Hydrogen bonding 4096: 4095: 4091: 4090: 4089: 4087: 4086: 4085: 4056: 4055: 4054: 4049: 3998: 3971: 3914: 3906: 3868: 3855: 3845: 3837: 3831: 3825: 3812: 3797: 3779: 3667: 3659: 3654: 3615:The Bubble Wall 3611: 3590: 3588:Further reading 3585: 3541: 3540: 3536: 3506: 3505: 3501: 3474:Acc. Chem. Res. 3467: 3466: 3459: 3412: 3411: 3407: 3398: 3394: 3353:(32): 11640–5. 3340: 3339: 3335: 3296:(23): 3129–38. 3283: 3282: 3278: 3248: 3247: 3243: 3213: 3212: 3208: 3198: 3197: 3193: 3155: 3154: 3150: 3113:(5762): 832–5. 3102: 3101: 3097: 3089:10.1139/v84-087 3069: 3068: 3064: 3057: 3042: 3041: 3037: 3014: 3013: 3009: 2970: 2969: 2965: 2934: 2933: 2926: 2917: 2915: 2906: 2905: 2901: 2875: 2874: 2870: 2848: 2847: 2843: 2836: 2815: 2814: 2810: 2780: 2779: 2775: 2727: 2726: 2722: 2692: 2691: 2687: 2657: 2656: 2652: 2631:(50): 16310–1. 2622: 2621: 2617: 2610: 2597: 2596: 2592: 2570: 2569: 2565: 2528: 2527: 2520: 2474: 2470: 2469: 2465: 2411: 2410: 2403: 2373: 2372: 2368: 2356: 2352: 2330: 2329: 2325: 2287: 2286: 2282: 2260: 2259: 2255: 2234:(9): 5216–300. 2225: 2224: 2220: 2211: 2209: 2205: 2154: 2149: 2143: 2139: 2126: 2122: 2098: 2097: 2090: 2064: 2063: 2059: 2021: 2020: 2016: 1986: 1985: 1981: 1965: 1961: 1945: 1941: 1918: 1917: 1913: 1891: 1890: 1886: 1855: 1854: 1850: 1825: 1821: 1801: 1797: 1781: 1777: 1761: 1757: 1713: 1712: 1703: 1694: 1692: 1624: 1623: 1619: 1575: 1574: 1570: 1522: 1521: 1517: 1465: 1464: 1460: 1456: 1432: 1416:metal complexes 1392:crystallography 1384:dihydrogen bond 1380: 1378:Dihydrogen bond 1371: 1367: 1344: 1278: 1261: 1243:nonbonded state 1239:partial charges 1176: 1172: 1165: 1157: 1144:protein folding 1131: 1120: 1105: 1086: 1030: 1020: 1016: 1012: 1009: 978:phosphoric acid 970: 966: 963: 959: 955: 951: 948: 944: 915: 841: 840: 826: 813: 758: 733: 708: 655:Compton profile 632: 628: 617: 613: 609: 606: 591: 587: 583: 557: 552: 551: 549: 538: 521: 517: 504: 500: 487: 483: 475:trigonal planar 470: 466: 453: 440: 430: 422: 419: 410: 406: 395: 384:crystallography 375: 368: 365: 364: 362: 356: 350: 344: 338: 331: 328: 327: 325: 321: 308: 305: 304: 302: 295: 285: 250: 227: 223: 180: 89: 82:electronegative 28: 23: 22: 15: 12: 11: 5: 4094: 4092: 4084: 4083: 4078: 4073: 4068: 4058: 4057: 4051: 4050: 4048: 4047: 4042: 4037: 4036: 4035: 4030: 4025: 4020: 4009: 4007: 4000: 3999: 3997: 3996: 3991: 3985: 3983: 3977: 3976: 3973: 3972: 3970: 3969: 3964: 3959: 3954: 3949: 3944: 3934: 3929: 3924: 3918: 3916: 3908: 3907: 3905: 3904: 3899: 3894: 3889: 3884: 3878: 3876: 3870: 3869: 3867: 3866: 3860: 3858: 3847: 3843:Intermolecular 3839: 3838: 3819: 3817: 3814: 3813: 3811: 3810: 3807: 3805: 3799: 3798: 3796: 3795: 3789: 3787: 3781: 3780: 3778: 3777: 3776: 3775: 3770: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3720: 3715: 3714: 3713: 3703: 3702: 3701: 3696: 3691: 3680: 3678: 3669: 3665:Intramolecular 3661: 3660: 3657:Chemical bonds 3655: 3653: 3652: 3645: 3638: 3630: 3624: 3623: 3618: 3610: 3609:External links 3607: 3606: 3605: 3589: 3586: 3584: 3583: 3554:(2): 323–339. 3534: 3515:(4): 337–341. 3499: 3480:(7): 348–354. 3457: 3405: 3392: 3333: 3276: 3241: 3206: 3191: 3148: 3095: 3082:(3): 526–530. 3062: 3055: 3035: 3007: 2980:(10): 104501. 2974:J. Chem. Phys. 2963: 2924: 2899: 2868: 2841: 2834: 2808: 2773: 2720: 2685: 2666:(3): 600–603. 2650: 2615: 2608: 2590: 2579:(3): 276–285. 2563: 2518: 2472: 2463: 2401: 2366: 2350: 2323: 2280: 2253: 2218: 2182:10.1.1.76.9448 2137: 2120: 2088: 2057: 2014: 1979: 1959: 1939: 1928:(1–2): 75–78. 1911: 1884: 1848: 1819: 1795: 1775: 1755: 1701: 1637:(18): 186102. 1617: 1568: 1515: 1457: 1455: 1452: 1431: 1428: 1388:intermolecular 1379: 1376: 1343: 1340: 1276: 1260: 1259:Other polymers 1257: 1223:ligand binding 1129: 1085: 1082: 1029: 1026: 1008: 1005: 1004: 1003: 1000: 985: 974: 941: 938: 931: 914: 911: 910: 909: 893: 886: 883: 880: 873: 866: 863: 860: 853: 825: 822: 812: 809: 793:molecular mass 757: 754: 732: 729: 707: 704: 700:NMR techniques 673:intramolecular 605: 602: 560: 542:H NMR spectrum 537: 534: 531: 530: 527: 524: 514: 513: 510: 507: 497: 496: 493: 490: 480: 479: 476: 473: 463: 462: 459: 456: 450: 449: 446: 445:VSEPR geometry 443: 429:, whereas the 418: 415: 394: 391: 379: 378: 360: 354: 348: 342: 336: 294: 291: 222: 219: 203:Intramolecular 192:self-assembled 188:intermolecular 186:An example of 179: 176: 166:structures of 120:intramolecular 116:intermolecular 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 4093: 4082: 4079: 4077: 4074: 4072: 4069: 4067: 4064: 4063: 4061: 4046: 4043: 4041: 4038: 4034: 4031: 4029: 4026: 4024: 4021: 4019: 4018:Hückel's rule 4016: 4015: 4014: 4011: 4010: 4008: 4005: 4001: 3995: 3992: 3990: 3987: 3986: 3984: 3982: 3981:Bond cleavage 3978: 3968: 3965: 3963: 3960: 3958: 3955: 3953: 3950: 3948: 3947:Intercalation 3945: 3942: 3938: 3937:Metallophilic 3935: 3933: 3930: 3928: 3925: 3923: 3920: 3919: 3917: 3913: 3909: 3903: 3900: 3898: 3895: 3893: 3890: 3888: 3885: 3883: 3880: 3879: 3877: 3875: 3871: 3865: 3862: 3861: 3859: 3857: 3854:Van der Waals 3851: 3848: 3844: 3840: 3835: 3829: 3823: 3809: 3808: 3806: 3804: 3800: 3794: 3791: 3790: 3788: 3786: 3782: 3774: 3771: 3769: 3766: 3765: 3764: 3761: 3759: 3756: 3754: 3751: 3749: 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3719: 3716: 3712: 3709: 3708: 3707: 3704: 3700: 3697: 3695: 3692: 3690: 3687: 3686: 3685: 3682: 3681: 3679: 3677: 3673: 3670: 3666: 3662: 3658: 3651: 3646: 3644: 3639: 3637: 3632: 3631: 3628: 3622: 3619: 3616: 3613: 3612: 3608: 3604: 3603:0-19-509549-9 3600: 3596: 3592: 3591: 3587: 3579: 3575: 3570: 3565: 3561: 3557: 3553: 3549: 3545: 3538: 3535: 3530: 3526: 3522: 3518: 3514: 3510: 3503: 3500: 3495: 3491: 3487: 3483: 3479: 3476: 3475: 3470: 3464: 3462: 3458: 3453: 3449: 3445: 3441: 3437: 3433: 3429: 3425: 3421: 3417: 3409: 3406: 3403: 3396: 3393: 3388: 3384: 3379: 3374: 3369: 3364: 3360: 3356: 3352: 3348: 3344: 3337: 3334: 3329: 3325: 3321: 3317: 3312: 3307: 3303: 3299: 3295: 3291: 3287: 3280: 3277: 3272: 3268: 3264: 3260: 3256: 3252: 3245: 3242: 3237: 3233: 3229: 3225: 3221: 3217: 3210: 3207: 3202: 3195: 3192: 3187: 3183: 3179: 3175: 3171: 3167: 3163: 3159: 3152: 3149: 3144: 3140: 3136: 3132: 3128: 3124: 3120: 3116: 3112: 3108: 3107: 3099: 3096: 3090: 3085: 3081: 3077: 3073: 3066: 3063: 3058: 3052: 3048: 3047: 3039: 3036: 3031: 3027: 3023: 3020: 3019: 3011: 3008: 3003: 2999: 2995: 2991: 2987: 2983: 2979: 2976: 2975: 2967: 2964: 2959: 2955: 2951: 2947: 2943: 2940: 2939: 2931: 2929: 2925: 2913: 2909: 2903: 2900: 2895: 2891: 2887: 2883: 2879: 2872: 2869: 2864: 2860: 2856: 2852: 2845: 2842: 2837: 2831: 2827: 2822: 2821: 2812: 2809: 2804: 2800: 2796: 2792: 2788: 2784: 2777: 2774: 2769: 2765: 2761: 2757: 2753: 2749: 2745: 2741: 2737: 2733: 2732: 2724: 2721: 2716: 2712: 2708: 2704: 2700: 2696: 2689: 2686: 2681: 2677: 2673: 2669: 2665: 2661: 2654: 2651: 2646: 2642: 2638: 2634: 2630: 2626: 2619: 2616: 2611: 2605: 2601: 2594: 2591: 2586: 2582: 2578: 2574: 2567: 2564: 2559: 2555: 2551: 2547: 2543: 2539: 2538: 2533: 2525: 2523: 2519: 2514: 2510: 2506: 2502: 2498: 2494: 2490: 2486: 2482: 2478: 2467: 2464: 2459: 2455: 2450: 2445: 2440: 2435: 2431: 2427: 2423: 2419: 2415: 2408: 2406: 2402: 2397: 2393: 2389: 2385: 2381: 2377: 2370: 2367: 2364: 2360: 2354: 2351: 2346: 2342: 2338: 2334: 2327: 2324: 2319: 2315: 2311: 2307: 2303: 2299: 2295: 2291: 2284: 2281: 2276: 2272: 2268: 2264: 2257: 2254: 2249: 2245: 2241: 2237: 2233: 2229: 2222: 2219: 2208:on 2014-08-13 2204: 2200: 2196: 2192: 2188: 2183: 2178: 2174: 2170: 2166: 2162: 2161: 2153: 2147: 2141: 2138: 2134: 2130: 2124: 2121: 2116: 2112: 2109:(1): 91–124. 2108: 2104: 2103: 2095: 2093: 2089: 2084: 2080: 2076: 2072: 2068: 2061: 2058: 2053: 2049: 2044: 2039: 2035: 2032: 2031: 2026: 2018: 2015: 2010: 2006: 2002: 1998: 1994: 1990: 1983: 1980: 1977: 1973: 1969: 1963: 1960: 1957: 1953: 1949: 1943: 1940: 1935: 1931: 1927: 1924: 1923: 1915: 1912: 1907: 1903: 1899: 1895: 1888: 1885: 1880: 1876: 1872: 1868: 1864: 1861: 1860: 1852: 1849: 1846: 1842: 1838: 1837:hydrogen bond 1834: 1833: 1828: 1823: 1820: 1817: 1813: 1809: 1805: 1799: 1796: 1793: 1789: 1785: 1779: 1776: 1773: 1769: 1765: 1762:Pimentel, G. 1759: 1756: 1751: 1747: 1743: 1739: 1734: 1729: 1725: 1721: 1717: 1710: 1708: 1706: 1702: 1691:on 2018-01-20 1690: 1686: 1682: 1678: 1674: 1670: 1666: 1662: 1658: 1654: 1650: 1645: 1640: 1636: 1632: 1628: 1621: 1618: 1613: 1609: 1604: 1599: 1595: 1591: 1587: 1583: 1579: 1572: 1569: 1564: 1560: 1556: 1552: 1548: 1544: 1539: 1534: 1531:(8): 085421. 1530: 1526: 1519: 1516: 1511: 1507: 1502: 1497: 1493: 1489: 1485: 1481: 1477: 1473: 1469: 1462: 1459: 1453: 1451: 1449: 1445: 1441: 1437: 1429: 1427: 1425: 1421: 1417: 1413: 1409: 1405: 1401: 1400:covalent bond 1397: 1393: 1389: 1385: 1377: 1375: 1365: 1361: 1357: 1353: 1349: 1341: 1339: 1337: 1333: 1329: 1325: 1321: 1317: 1314: 1310: 1306: 1302: 1298: 1294: 1290: 1286: 1273: 1265: 1258: 1256: 1254: 1250: 1248: 1244: 1240: 1236: 1232: 1228: 1227:electrostatic 1224: 1220: 1215: 1211: 1209: 1205: 1201: 1197: 1192: 1190: 1186: 1182: 1168: 1163: 1155: 1151: 1147: 1145: 1141: 1137: 1133: 1123: 1118: 1114: 1108: 1103: 1099: 1095: 1091: 1083: 1081: 1079: 1075: 1071: 1067: 1058: 1054: 1050: 1045: 1039: 1034: 1027: 1025: 1006: 1001: 998: 997:ideal gas law 994: 990: 986: 983: 979: 975: 942: 939: 936: 932: 929: 925: 924:boiling point 921: 920:melting point 917: 916: 912: 891: 884: 881: 878: 871: 864: 861: 858: 851: 839: 838: 837: 835: 831: 828:For example, 824:Other liquids 823: 821: 817: 810: 808: 804: 801: 796: 794: 790: 789:boiling point 787:water's high 786: 782: 780: 776: 771: 767: 763: 755: 750: 747:Structure of 745: 737: 730: 728: 726: 722: 718: 713: 712:Linus Pauling 705: 703: 701: 697: 696:Linus Pauling 693: 689: 685: 681: 677: 674: 670: 667: 666:electrostatic 663: 658: 656: 652: 647: 645: 641: 636: 626: 621: 603: 601: 598: 580: 558: 547: 546:acetylacetone 543: 535: 528: 525: 516: 515: 511: 508: 499: 498: 494: 491: 482: 481: 477: 474: 465: 464: 460: 457: 452: 451: 447: 444: 439: 438: 435: 428: 416: 414: 404: 403:electrostatic 400: 392: 390: 387: 385: 361: 355: 349: 343: 337: 320: 319: 318: 316: 300: 293:Bond strength 292: 289: 281: 279: 278: 273: 268: 264: 262: 261:London forces 253: 247: 239: 235: 233: 220: 215: 212: 208: 207:acetylacetone 204: 200: 193: 189: 184: 177: 175: 173: 172:nucleic acids 169: 165: 161: 157: 153: 147: 145: 141: 137: 133: 129: 125: 121: 117: 112: 110: 106: 102: 99: 95: 94:covalent bond 87: 83: 79: 75: 71: 70:electrostatic 67: 63: 62:hydrogen bond 59: 51: 47: 43: 37: 32: 19: 4023:Baird's rule 3873: 3743:Charge-shift 3706:Hypervalence 3594: 3551: 3548:Metabolomics 3547: 3537: 3512: 3508: 3502: 3477: 3472: 3419: 3415: 3408: 3395: 3350: 3346: 3336: 3293: 3289: 3279: 3254: 3250: 3244: 3219: 3215: 3209: 3203:. Wiley-VCH. 3200: 3194: 3161: 3157: 3151: 3110: 3104: 3098: 3079: 3076:Can. J. Chem 3075: 3065: 3045: 3038: 3024:(14): 4196. 3021: 3016: 3010: 2977: 2972: 2966: 2941: 2936: 2916:. Retrieved 2914:. 2017-06-29 2911: 2902: 2885: 2881: 2871: 2854: 2851:J. Chem. Soc 2850: 2844: 2819: 2811: 2789:(1): 51–65. 2786: 2782: 2776: 2738:(2): 510–2. 2735: 2731:J Magn Reson 2729: 2723: 2698: 2694: 2688: 2663: 2659: 2653: 2628: 2624: 2618: 2602:. Springer. 2599: 2593: 2576: 2572: 2566: 2541: 2535: 2480: 2476: 2466: 2421: 2417: 2379: 2375: 2369: 2353: 2336: 2332: 2326: 2293: 2289: 2283: 2266: 2262: 2256: 2231: 2227: 2221: 2210:. Retrieved 2203:the original 2164: 2158: 2140: 2135:, chapter 3. 2132: 2128: 2123: 2106: 2100: 2074: 2070: 2060: 2033: 2028: 2017: 1992: 1988: 1982: 1967: 1962: 1947: 1942: 1925: 1920: 1914: 1897: 1893: 1887: 1865:(1): 48–76. 1862: 1857: 1851: 1830: 1822: 1807: 1803: 1798: 1783: 1778: 1763: 1758: 1723: 1719: 1693:. Retrieved 1689:the original 1634: 1630: 1620: 1585: 1581: 1571: 1528: 1524: 1518: 1475: 1471: 1461: 1433: 1381: 1345: 1308: 1282: 1251: 1216: 1212: 1193: 1166: 1161: 1148: 1121: 1116: 1106: 1101: 1087: 1072:(as well as 1062: 1038:double helix 1010: 827: 818: 814: 805: 797: 783: 759: 709: 676:bound states 669:scalar field 659: 651:anisotropies 648: 637: 622: 607: 581: 539: 536:Spectroscopy 420: 398: 396: 388: 380: 296: 283: 275: 269: 265: 258: 251: 231: 224: 148: 113: 65: 61: 55: 4013:Aromaticity 3989:Heterolysis 3967:Salt bridge 3912:Noncovalent 3882:Low-barrier 3763:Aromaticity 3753:Conjugation 3733:Pi backbond 2944:(6): 1381. 2544:(4): 1276. 1669:1874/307996 1360:formic acid 1160:of residue 1113:alpha helix 1078:replication 1074:pi stacking 770:water dimer 688:bound state 684:ionic bonds 664:-dependent 548:appears at 313:). Typical 144:felted wool 132:ionic bonds 4060:Categories 3941:aurophilic 3922:Mechanical 3164:(2): 485. 2938:Mol. Phys. 2918:2024-06-22 2212:2017-10-25 1976:0471252905 1956:0198509707 1816:3540579036 1810:Springer; 1808:1994, 2012 1792:0195095499 1772:0343171600 1695:2017-08-30 1454:References 1396:ionic bond 1364:bifluoride 1136:beta sheet 1098:amino acid 1070:base pairs 1057:base pairs 928:solubility 448:Angle (°) 315:enthalpies 299:bifluoride 80:to a more 4033:spherical 3994:Homolysis 3957:Cation–pi 3932:Chalcogen 3892:Symmetric 3748:Hapticity 3444:1089-5639 2715:0002-7863 2376:Chem. Rev 2177:CiteSeerX 1742:1365-3075 1644:1410.1933 1538:1406.3562 1408:chalcogen 1285:cellulose 1196:trehalose 1185:threonine 1126:, then a 935:azeotropy 933:Negative 892:− 885:⋅ 882:⋅ 879:⋅ 872:− 865:⋅ 862:⋅ 859:⋅ 852:− 559:δ 509:pyramidal 492:pyramidal 160:secondary 107:(O), and 86:lone pair 58:chemistry 48:image of 3962:Anion–pi 3952:Stacking 3874:Hydrogen 3785:Metallic 3676:Covalent 3668:(strong) 3578:25750602 3529:24981612 3494:19904922 3452:16833488 3387:15289598 3328:22090973 3320:17952367 3311:11136444 3271:26598272 3236:20657920 3216:ChemComm 3186:17648714 3135:16439623 3002:16178604 2857:: 1635. 2760:10497060 2645:15600318 2558:84176511 2505:15758995 2458:24591597 2396:11749346 2318:29048895 2248:27136957 2199:17388314 2052:97688573 2009:21611676 1879:12491444 1750:97688573 1677:25396382 1612:28880549 1563:53610973 1510:24875276 1478:: 3931. 1444:hydrogen 1440:nitrogen 1412:pi-bonds 1404:nitrogen 1336:nylon-11 1320:humidity 1303:and the 1301:carbonyl 1235:carbonyl 1219:dehydron 1200:sorbitol 1189:cysteine 1084:Proteins 1053:cytosine 982:glycerol 680:covalent 526:trigonal 214:tautomer 168:proteins 164:tertiary 128:covalent 109:fluorine 101:nitrogen 74:hydrogen 3927:Halogen 3773:bicyclo 3718:Agostic 3569:4342520 3424:Bibcode 3355:Bibcode 3166:Bibcode 3143:6707413 3115:Bibcode 3106:Science 2982:Bibcode 2946:Bibcode 2791:Bibcode 2740:Bibcode 2668:Bibcode 2513:4396493 2485:Bibcode 2449:3964065 2426:Bibcode 2339:: 467. 2298:Bibcode 2169:Bibcode 1685:8309018 1649:Bibcode 1543:Bibcode 1501:4050271 1480:Bibcode 1332:nylon 6 1328:aramids 1088:In the 1049:guanine 980:and of 834:ammonia 721:Latimer 706:History 653:in the 577:⁠ 550:⁠ 178:Bonding 4028:Möbius 3856:forces 3846:(weak) 3601: 3576: 3566: 3527: 3492: 3450: 3442: 3385: 3378:511032 3375: 3326: 3318: 3308: 3269: 3234: 3184: 3141: 3133: 3053: 3000: 2832: 2768:121429 2766: 2758: 2713: 2643: 2606: 2556: 2511: 2503: 2477:Nature 2456: 2446: 2394: 2361: 2316: 2246: 2197: 2179: 2050: 2007: 1974: 1954: 1877: 1814: 1790: 1770: 1748: 1740: 1683: 1675: 1610: 1561: 1508: 1498: 1448:oxygen 1406:, and 1398:, and 1330:, and 1324:nylons 1313:aramid 1289:cotton 1187:, and 1181:serine 1059:in DNA 1019:, and 785:Liquid 662:metric 458:linear 105:oxygen 66:H-bond 4006:rules 3915:other 3803:Ionic 3711:3c–4e 3699:8c–2e 3694:4c–2e 3689:3c–2e 3324:S2CID 3182:S2CID 3139:S2CID 2764:S2CID 2554:S2CID 2509:S2CID 2206:(PDF) 2155:(PDF) 2048:S2CID 1827:IUPAC 1746:S2CID 1681:S2CID 1639:arXiv 1559:S2CID 1533:arXiv 1316:fibre 1305:amide 1297:nylon 1295:. In 1231:amide 1132:helix 1111:, an 1094:amide 800:TIP4P 766:water 762:water 756:Water 610:O:H−O 301:ion, 272:IUPAC 252:green 152:water 140:paper 111:(F). 103:(N), 36:water 3768:homo 3723:Bent 3599:ISBN 3574:PMID 3525:PMID 3490:PMID 3448:PMID 3440:ISSN 3383:PMID 3316:PMID 3267:PMID 3232:PMID 3131:PMID 3051:ISBN 2998:PMID 2830:ISBN 2756:PMID 2711:ISSN 2641:PMID 2604:ISBN 2501:PMID 2475:O". 2454:PMID 2392:PMID 2359:ISBN 2314:PMID 2244:PMID 2195:PMID 2133:2018 2005:PMID 1972:ISBN 1952:ISBN 1948:2001 1875:PMID 1812:ISBN 1788:ISBN 1768:ISBN 1738:ISSN 1673:PMID 1608:PMID 1506:PMID 1446:and 1366:ion 1358:and 1293:flax 1291:and 1253:Wool 1233:and 1198:and 1119:and 1104:and 1051:and 529:142 478:120 461:180 421:The 397:The 211:enol 170:and 162:and 142:and 64:(or 60:, a 3564:PMC 3556:doi 3517:doi 3482:doi 3432:doi 3420:109 3373:PMC 3363:doi 3351:101 3306:PMC 3298:doi 3259:doi 3224:doi 3174:doi 3162:106 3123:doi 3111:311 3084:doi 3026:doi 3022:108 2990:doi 2978:123 2954:doi 2890:doi 2859:doi 2855:101 2826:450 2799:doi 2748:doi 2736:140 2703:doi 2699:122 2676:doi 2633:doi 2629:126 2581:doi 2546:doi 2493:doi 2481:434 2444:PMC 2434:doi 2422:111 2384:doi 2380:100 2341:doi 2306:doi 2294:121 2271:doi 2267:121 2236:doi 2232:116 2187:doi 2165:111 2111:doi 2079:doi 2038:doi 1997:doi 1930:doi 1902:doi 1867:doi 1841:doi 1839:". 1728:doi 1665:hdl 1657:doi 1635:113 1598:hdl 1590:doi 1551:doi 1496:PMC 1488:doi 1414:or 1173:N−H 1169:+ 4 1158:C=O 1146:). 1124:+ 3 1109:+ 4 1066:DNA 1028:DNA 1021:C−N 1017:C−O 1013:C−C 779:ice 777:of 682:or 618:O−O 614:H−O 592:X−H 588:X−H 584:X−H 512:89 495:46 423:X−H 409:or 286:X−H 263:). 130:or 56:In 46:AFM 4062:: 3572:. 3562:. 3552:11 3550:. 3546:. 3523:. 3511:. 3488:. 3478:29 3460:^ 3446:. 3438:. 3430:. 3418:. 3381:. 3371:. 3361:. 3349:. 3345:. 3322:. 3314:. 3304:. 3294:64 3292:. 3288:. 3265:. 3253:. 3230:. 3220:46 3218:. 3180:. 3172:. 3160:. 3137:. 3129:. 3121:. 3109:. 3080:62 3078:. 3074:. 2996:. 2988:. 2952:. 2942:56 2927:^ 2910:. 2886:42 2884:. 2880:. 2853:. 2828:. 2797:. 2787:44 2785:. 2762:. 2754:. 2746:. 2734:. 2709:. 2697:. 2674:. 2664:82 2662:. 2639:. 2627:. 2577:15 2575:. 2552:. 2540:. 2534:. 2521:^ 2507:. 2499:. 2491:. 2479:. 2452:. 2442:. 2432:. 2420:. 2416:. 2404:^ 2390:. 2378:. 2337:16 2335:. 2312:. 2304:. 2292:. 2265:. 2242:. 2230:. 2193:. 2185:. 2175:. 2163:. 2157:. 2105:. 2091:^ 2075:23 2073:. 2069:. 2046:. 2034:83 2027:. 2003:. 1993:13 1991:. 1950:, 1926:37 1898:93 1896:. 1873:. 1863:41 1829:, 1744:. 1736:. 1724:83 1722:. 1718:. 1704:^ 1679:. 1671:. 1663:. 1655:. 1647:. 1633:. 1629:. 1606:. 1596:. 1586:18 1584:. 1580:. 1557:. 1549:. 1541:. 1529:90 1527:. 1504:. 1494:. 1486:. 1474:. 1470:. 1346:A 1338:. 1249:. 1183:, 1130:10 1080:. 1015:, 965:, 960:PH 950:, 945:NH 926:, 922:, 518:SO 427:pm 413:. 363:OH 326:HF 303:HF 234:. 174:. 3943:) 3939:( 3649:e 3642:t 3635:v 3580:. 3558:: 3531:. 3519:: 3513:1 3496:. 3484:: 3454:. 3434:: 3426:: 3389:. 3365:: 3357:: 3330:. 3300:: 3273:. 3261:: 3255:7 3238:. 3226:: 3188:. 3176:: 3168:: 3145:. 3125:: 3117:: 3092:. 3086:: 3059:. 3032:. 3028:: 3004:. 2992:: 2984:: 2960:. 2956:: 2948:: 2921:. 2896:. 2892:: 2865:. 2861:: 2838:. 2805:. 2801:: 2793:: 2770:. 2750:: 2742:: 2717:. 2705:: 2682:. 2678:: 2670:: 2647:. 2635:: 2612:. 2587:. 2583:: 2560:. 2548:: 2542:8 2515:. 2495:: 2487:: 2473:2 2460:. 2436:: 2428:: 2398:. 2386:: 2347:. 2343:: 2320:. 2308:: 2300:: 2277:. 2273:: 2250:. 2238:: 2215:. 2189:: 2171:: 2117:. 2113:: 2107:9 2085:. 2081:: 2054:. 2040:: 2011:. 1999:: 1936:. 1932:: 1908:. 1904:: 1881:. 1869:: 1843:: 1752:. 1730:: 1698:. 1667:: 1659:: 1651:: 1641:: 1614:. 1600:: 1592:: 1565:. 1553:: 1545:: 1535:: 1512:. 1490:: 1482:: 1476:5 1442:– 1309:H 1307:N 1277:α 1177:H 1167:i 1162:i 1128:3 1122:i 1117:i 1107:i 1102:i 999:. 984:. 971:S 969:2 967:H 962:3 956:O 954:2 952:H 947:3 896:F 888:H 876:F 868:H 856:F 848:H 563:H 520:2 503:2 501:H 486:2 484:H 469:2 467:H 374:2 369:3 366:+ 332:2 329:− 309:2 306:− 216:. 20:)

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.

Index