339:
Most salts form crystals with characteristic distances between the ions; in contrast to many other noncovalent interactions, salt bridges are not directional and show in the solid state usually contact determined only by the van der Waals radii of the ions. Inorganic as well as organic ions display in water at moderate ionic strength I similar salt bridge as association ÎG values around 5 to 6 kJ/mol for a 1:1 combination of anion and cation, almost independent of the nature (size, polarizability, etc.) of the ions. The ÎG values are additive and approximately a linear function of the charges, the interaction of e.g. a doubly charged phosphate anion with a single charged ammonium cation accounts for about 2x5 = 10 kJ/mol. The ÎG values depend on the ionic strength I of the solution, as described by the Debye-HĂŒckel equation, at zero ionic strength one observes ÎG = 8 kJ/mol.
975:
electron clouds in non-polar molecules. Thus, London interactions are caused by random fluctuations of electron density in an electron cloud. An atom with a large number of electrons will have a greater associated London force than an atom with fewer electrons. The dispersion (London) force is the most important component because all materials are polarizable, whereas Keesom and Debye forces require permanent dipoles. The London interaction is universal and is present in atom-atom interactions as well. For various reasons, London interactions (dispersion) have been considered relevant for interactions between macroscopic bodies in condensed systems.
284:
2494:
544:
power of the distance, unlike the interaction energy of two spatially fixed dipoles, which depends on the inverse third power of the distance. The Keesom interaction can only occur among molecules that possess permanent dipole moments, i.e., two polar molecules. Also Keesom interactions are very weak van der Waals interactions and do not occur in aqueous solutions that contain electrolytes. The angle averaged interaction is given by the following equation:
785:
molecule's electrons. A molecule with permanent dipole can induce a dipole in a similar neighboring molecule and cause mutual attraction. Debye forces cannot occur between atoms. The forces between induced and permanent dipoles are not as temperature dependent as Keesom interactions because the induced dipole is free to shift and rotate around the polar molecule. The Debye induction effects and Keesom orientation effects are termed polar interactions.
2488:
280:. The number of Hydrogen bonds formed between molecules is equal to the number of active pairs. The molecule which donates its hydrogen is termed the donor molecule, while the molecule containing lone pair participating in H bonding is termed the acceptor molecule. The number of active pairs is equal to the common number between number of hydrogens the donor has and the number of lone pairs the acceptor has.
2500:
463:
210:, but several such weak interactions with the required spatial configuration of the active center of the enzyme lead to significant restructuring changes the energy state of molecules or substrate, which ultimately leads to the breaking of some and the formation of other covalent chemical bonds. Strictly speaking, all
1151:
When a gas is compressed to increase its density, the influence of the attractive force increases. If the gas is made sufficiently dense, the attractions can become large enough to overcome the tendency of thermal motion to cause the molecules to disperse. Then the gas can condense to form a solid or
784:
The second contribution is the induction (also termed polarization) or Debye force, arising from interactions between rotating permanent dipoles and from the polarizability of atoms and molecules (induced dipoles). These induced dipoles occur when one molecule with a permanent dipole repels another
974:
The third and dominant contribution is the dispersion or London force (fluctuating dipoleâinduced dipole), which arises due to the non-zero instantaneous dipole moments of all atoms and molecules. Such polarization can be induced either by a polar molecule or by the repulsion of negatively charged
803:
One example of an induction interaction between permanent dipole and induced dipole is the interaction between HCl and Ar. In this system, Ar experiences a dipole as its electrons are attracted (to the H side of HCl) or repelled (from the Cl side) by HCl. The angle averaged interaction is given by
543:
averaged over different rotational orientations of the dipoles. It is assumed that the molecules are constantly rotating and never get locked into place. This is a good assumption, but at some point molecules do get locked into place. The energy of a Keesom interaction depends on the inverse sixth
347:
Dipoleâdipole interactions (or Keesom interactions) are electrostatic interactions between molecules which have permanent dipoles. This interaction is stronger than the London forces but is weaker than ion-ion interaction because only partial charges are involved. These interactions tend to align
491:
Ionâdipole and ionâinduced dipole forces are similar to dipoleâdipole and dipoleâinduced dipole interactions but involve ions, instead of only polar and non-polar molecules. Ionâdipole and ionâinduced dipole forces are stronger than dipoleâdipole interactions because the charge of any ion is much
338:
The attraction between cationic and anionic sites is a noncovalent, or intermolecular interaction which is usually referred to as ion pairing or salt bridge. It is essentially due to electrostatic forces, although in aqueous medium the association is driven by entropy and often even endothermic.
1166:
Intermolecular forces observed between atoms and molecules can be described phenomenologically as occurring between permanent and instantaneous dipoles, as outlined above. Alternatively, one may seek a fundamental, unifying theory that is able to explain the various types of interactions such as
1187:
methods, such a quantum mechanical explanation of intermolecular interactions provides an array of approximate methods that can be used to analyze intermolecular interactions. One of the most helpful methods to visualize this kind of intermolecular interactions, that we can find in quantum
291:
Though both not depicted in the diagram, water molecules have four active bonds. The oxygen atomâs two lone pairs interact with a hydrogen each, forming two additional hydrogen bonds, and the second hydrogen atom also interacts with a neighbouring oxygen. Intermolecular hydrogen bonding is
1079:
This comparison is approximate. The actual relative strengths will vary depending on the molecules involved. For instance, the presence of water creates competing interactions that greatly weaken the strength of both ionic and hydrogen bonds. We may consider that for static systems,
374:
495:
An ionâdipole force consists of an ion and a polar molecule interacting. They align so that the positive and negative groups are next to one another, allowing maximum attraction. An important example of this interaction is hydration of ions in water which give rise to
518:
The van der Waals forces arise from interaction between uncharged atoms or molecules, leading not only to such phenomena as the cohesion of condensed phases and physical absorption of gases, but also to a universal force of attraction between macroscopic bodies.
678:
500:. The polar water molecules surround themselves around ions in water and the energy released during the process is known as hydration enthalpy. The interaction has its immense importance in justifying the stability of various ions (like Cu) in water.
1195:
Concerning electron density topology, recent methods based on electron density gradient methods have emerged recently, notably with the development of IBSI (Intrinsic Bond
Strength Index), relying on the IGM (Independent Gradient Model) methodology.
920:
1132:
at the same temperature and pressure. The attractive force draws molecules closer together and gives a real gas a tendency to occupy a smaller volume than an ideal gas. Which interaction is more important depends on temperature and pressure (see
527:
The first contribution to van der Waals forces is due to electrostatic interactions between rotating permanent dipoles, quadrupoles (all molecules with symmetry lower than cubic), and multipoles. It is termed the
356:(HCl): the positive end of a polar molecule will attract the negative end of the other molecule and influence its position. Polar molecules have a net attraction between them. Examples of polar molecules include
503:
An ionâinduced dipole force consists of an ion and a non-polar molecule interacting. Like a dipoleâinduced dipole force, the charge of the ion causes distortion of the electron cloud on the non-polar molecule.
955:
This kind of interaction can be expected between any polar molecule and non-polar/symmetrical molecule. The induction-interaction force is far weaker than dipoleâdipole interaction, but stronger than the
458:{\displaystyle {\overset {\color {Red}\delta +}{{\ce {H}}}}-{\overset {\color {Red}\delta -}{{\ce {Cl}}}}\cdots {\overset {\color {Red}\delta +}{{\ce {H}}}}-{\overset {\color {Red}\delta -}{{\ce {Cl}}}}}
1148:
is the measure of thermal energy, so increasing temperature reduces the influence of the attractive force. In contrast, the influence of the repulsive force is essentially unaffected by temperature.
1152:
liquid, i.e., a condensed phase. Lower temperature favors the formation of a condensed phase. In a condensed phase, there is very nearly a balance between the attractive and repulsive forces.
550:
1140:
In a gas, the distances between molecules are generally large, so intermolecular forces have only a small effect. The attractive force is not overcome by the repulsive force, but by the
268:. The hydrogen bond is often described as a strong electrostatic dipoleâdipole interaction. However, it also has some features of covalent bonding: it is directional, stronger than a
810:
792:), which is the attractive interaction between a permanent multipole on one molecule with an induced (by the former di/multi-pole) 31 on another. This interaction is called the
739:
712:
770:
950:
979:
developed the theory of van der Waals between macroscopic bodies in 1937 and showed that the additivity of these interactions renders them considerably more long-range.
51:, involving sharing electron pairs between atoms, is much stronger than the forces present between neighboring molecules. Both sets of forces are essential parts of
472:
on the molecule as a whole. This occurs if there is symmetry within the molecule that causes the dipoles to cancel each other out. This occurs in molecules such as
186:) in which the formation of chemical, that is, ionic, covalent or metallic bonds does not occur. In other words, these interactions are significantly weaker than
1256:
2253:
Ponce-Vargas M, Lefebvre C, Boisson JC, HĂ©non E (January 2020). "Atomic
Decomposition Scheme of Noncovalent Interactions Applied to Host-Guest Assemblies".
1523:
1353:"Biochemistry and Molecular Biology - Paperback - Despo Papachristodoulou, Alison Snape, William H. Elliott, Daphne C. Elliott - Oxford University Press"
1375:
2163:"Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient versus electron density"
2587:
1612:"The second virial coefficient for rigid spherical molecules whose mutual attraction is equivalent to that of a quadruplet placed at its center"
2213:"The Independent Gradient Model: A New Approach for Probing Strong and Weak Interactions in Molecules from Wave Function Calculations"
2705:
2632:
2313:
1211:
333:
133:
2741:
1124:). In a gas, the repulsive force chiefly has the effect of keeping two molecules from occupying the same volume. This gives a
1841:
1806:
1756:
1506:
1446:
1422:
1336:
2104:
480:. The dipoleâdipole interaction between two individual atoms is usually zero, since atoms rarely carry a permanent dipole.
536:. These forces originate from the attraction between permanent dipoles (dipolar molecules) and are temperature dependent.
2627:
1246:
1088:
will always be stronger than intermolecular forces in any given substance. But it is not so for big moving systems like
1352:
673:{\displaystyle {\frac {-d_{1}^{2}d_{2}^{2}}{24\pi ^{2}\varepsilon _{0}^{2}\varepsilon _{r}^{2}k_{\text{B}}Tr^{6}}}=V,}
70:
published in Paris in 1743. Other scientists who have contributed to the investigation of microscopic forces include:
2552:
2376:
1331:. International Series of Monographs in Natural Philosophy. Vol. 18 (1st ed.). Oxford: Pergamon Press.
1189:
2567:
483:
The Keesom interaction is a van der Waals force. It is discussed further in the section "Van der Waals forces".
2731:
2403:
2364:
2354:
1867:"Conformational proofreading: the impact of conformational changes on the specificity of molecular recognition"
1531:
300:, which have little capability to hydrogen bond. Intramolecular hydrogen bonding is partly responsible for the
2359:
2162:
1192:, which is based on the electron density of the system. London dispersion forces play a big role with this.
1161:
2306:
915:{\displaystyle {\frac {-d_{1}^{2}\alpha _{2}}{16\pi ^{2}\varepsilon _{0}^{2}\varepsilon _{r}^{2}r^{6}}}=V,}
1772:
1561:"Theoretical models for surface forces and adhesion and their measurement using atomic force microscopy"
105:
276:, and usually involves a limited number of interaction partners, which can be interpreted as a kind of
207:
717:
690:
2736:
2622:
2612:
2602:
2577:
2547:
1261:
1216:
1145:
1677:
Roberts JK, Orr WJ (1938). "Induced dipoles and the heat of adsorption of argon on ionic crystals".
1462:
Biedermann F, Schneider HJ (May 2016). "Experimental
Binding Energies in Supramolecular Complexes".
2393:
748:
492:
greater than the charge of a dipole moment. Ionâdipole bonding is stronger than hydrogen bonding.
2654:
2557:
2529:
2299:
1925:
1287:
1221:
1121:
1120:
Intermolecular forces are repulsive at short distances and attractive at long distances (see the
969:
957:
928:
164:
123:
52:
139:
Information on intermolecular forces is obtained by macroscopic measurements of properties like
1134:
469:
128:
2062:
1639:
Blustin PH (1978). "A Floating
Gaussian Orbital calculation on argon hydrochloride (Ar·HCl)".
2698:
2659:
2212:
1966:
1093:
533:
297:
215:
2693:
2211:
Lefebvre C, Khartabil H, Boisson JC, Contreras-GarcĂa J, Piquemal JP, HĂ©non E (March 2018).
2004:
Arunan E, Desiraju GR, Klein RA, Sadlej J, Scheiner S, Alkorta I, et al. (2011-07-08).
2617:
2371:
2330:
2177:
2119:
1937:
1878:
1713:
1299:
1231:
1100:) bonds form an active intermediate state where the intermolecular bonds cause some of the
789:
309:
273:
191:
160:
75:
71:
44:
963:
8:
2519:
2383:
2349:
2103:
Klein J, Khartabil H, Boisson JC, Contreras-GarcĂa J, Piquemal JP, HĂ©non E (March 2020).
1833:
1704:
Sapse AM, Rayez-Meaume MT, Rayez JC, Massa LJ (1979). "Ion-induced dipole Hân clusters".
1251:
1180:
1172:
513:
301:
277:
269:
111:
79:
56:
2683:
2181:
2123:
1941:
1882:
1717:
1611:
1303:
170:
In the broadest sense, it can be understood as such interactions between any particles (
2438:
2278:
2161:
Lefebvre C, Rubez G, Khartabil H, Boisson JC, Contreras-GarcĂa J, HĂ©non E (July 2017).
2143:
2035:
1901:
1866:
1729:
1656:
1587:
1560:
1226:
540:
473:
305:
148:
218:
and the enzyme, therefore the importance of these interactions is especially great in
2669:
2458:
2418:
2408:
2282:
2270:
2235:
2193:
2147:
2135:
2055:
2027:
1986:
1906:
1847:
1837:
1802:
1752:
1592:
1502:
1479:
1442:
1418:
1332:
1184:
1176:
797:
357:
353:
253:
223:
2039:
1660:
1385:
2710:
2450:
2423:
2262:
2227:
2185:
2127:
2085:
2017:
1978:
1945:
1896:
1886:
1733:
1721:
1686:
1648:
1582:
1572:
1471:
1410:
1389:
1380:
1307:
1168:
1105:
1104:
to be broken, while the others are formed, in this way proceeding the thousands of
497:
349:
248:
is an extreme form of dipole-dipole bonding, referring to the attraction between a
211:
83:
32:
2688:
2562:
2433:
1891:
1829:
1236:
1175:
and dipoleâdipole interactions. Typically, this is done by applying the ideas of
63:
1950:
1475:
1414:
1312:
2597:
2398:
1141:
976:
477:
283:
152:
2725:
2646:
2606:
2539:
2493:
2468:
2341:
2322:
2266:
2131:
2031:
2022:
2005:
1990:
1851:
1384:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1206:
1101:
1097:
1085:
1081:
1035:
239:
194:
of the interacting particles. (This is only partially true. For example, all
187:
183:
156:
144:
97:
87:
48:
1405:
Lindh U (2013), "Biological functions of the elements", in
Selinus O (ed.),
1393:
16:
Force of attraction or repulsion between molecules and neighboring particles
2592:
2274:
2239:
2231:
2197:
2139:
1982:
1910:
1596:
1483:
317:
219:
115:
93:
Attractive intermolecular forces are categorized into the following types:
1823:
1577:
272:
interaction, produces interatomic distances shorter than the sum of their
31:) is the force that mediates interaction between molecules, including the
2678:
2428:
1690:
119:
2210:
2089:
202:
begin with a weak intermolecular interaction between a substrate and an
35:
which act between atoms and other types of neighbouring particles, e.g.
2189:
1652:
1559:
Leite FL, Bueno CC, Da RĂłz AL, Ziemath EC, Oliveira ON (October 2012).
1183:
has been especially effective in this regard. When applied to existing
964:
London dispersion force (fluctuating dipoleâinduced dipole interaction)
361:
1751:(5th ed.). Boston: Houghton Mifflin Company. pp. 30â33, 67.
2413:
2388:
2102:
1725:
1266:
1129:
522:
468:
Often molecules contain dipolar groups of atoms, but have no overall
199:
140:
62:
The first reference to the nature of microscopic forces is found in
2487:
1125:
1109:
321:
265:
257:
249:
171:
779:
2291:
1619:
Proceedings of the Royal
Netherlands Academy of Arts and Sciences
1241:
788:
The induced dipole forces appear from the induction (also termed
539:
They consist of attractive interactions between dipoles that are
313:
2252:
1089:
261:
227:
203:
195:
2006:"Definition of the hydrogen bond (IUPAC Recommendations 2011)"
1073:
Estimated from the enthalpies of vaporization of hydrocarbons
47:â the forces which hold a molecule together. For example, the
2160:
293:
1965:
Lenhard, Johannes; Stephan, Simon; Hasse, Hans (June 2024).
352:). An example of a dipoleâdipole interaction can be seen in
1926:"On the history of key empirical intermolecular potentials"
1703:
1409:(Revised ed.), Dordrecht: Springer, pp. 129â177,
1288:"On the history of key empirical intermolecular potentials"
486:
190:
ones and do not lead to a significant restructuring of the
175:
36:
2499:
1790:
1439:
1096:
molecules. Here the numerous intramolecular (most often -
2003:
342:
179:
40:
1740:
147:(PVT) data. The link to microscopic aspects is given by
1558:
1257:
Comparison of software for molecular mechanics modeling
320:. It also plays an important role in the structure of
1501:. United States: Pearson Education Inc. p. 466.
931:
813:
751:
720:
693:
553:
377:
1964:
1672:
1670:
1461:
1162:
Covalent bond § Quantum mechanical description
523:Keesom force (permanent dipole â permanent dipole)
214:begin with intermolecular interactions between the
2054:
1924:Fischer, Johann; Wendland, Martin (October 2023).
1515:
1286:Fischer, Johann; Wendland, Martin (October 2023).
1115:
944:
914:
764:
733:
706:
672:
457:
33:electromagnetic forces of attraction or repulsion
2723:
1697:
1667:
1046:About 5 kcal/mol (21 kJ/mol) in water
780:Debye force (permanent dipolesâinduced dipoles)
1967:"On the History of the Lennard-Jones Potential"
1923:
1799:Enthalpies of Vaporization of Organic Compounds
1634:
1632:
1326:
1285:
741:= dielectric constant of surrounding material,
348:the molecules to increase attraction (reducing
2076:King M (1976). "Theory of the Chemical Bond".
2052:
1765:
1369:
1155:
982:
102:Ionâdipole forces and ionâinduced dipole force
2307:
1436:
1128:a tendency to occupy a larger volume than an
43:. Intermolecular forces are weak relative to
2255:Journal of Chemical Information and Modeling
1796:
1629:
252:atom that is bonded to an element with high
1864:
1749:Organic Chemistry: Structure and Reactivity
1565:International Journal of Molecular Sciences
1441:. Hoboken, NJ: John Wiley & Sons, Inc.
2314:
2300:
1676:
292:responsible for the high boiling point of
2021:
1949:
1900:
1890:
1586:
1576:
1311:
2706:Polyhedral skeletal electron pair theory
2078:Journal of the American Chemical Society
487:Ionâdipole and ionâinduced dipole forces
334:Salt bridge (protein and supramolecular)
282:
134:Salt bridge (protein and supramolecular)
1821:
1638:
1179:to molecules, and RayleighâSchrödinger
507:
343:Dipoleâdipole and similar interactions
2724:
1609:
1521:
2295:
1554:
1552:
1550:
1548:
1404:
445:
425:
405:
385:
2075:
1822:Alberts, Bruce; et al. (2015).
296:(100 °C) compared to the other
2170:Physical Chemistry Chemical Physics
2112:The Journal of Physical Chemistry A
2105:"New Way for Probing Bond Strength"
2057:Electrodynamics of Continuous Media
1746:
1679:Transactions of the Faraday Society
1496:
1247:Quantum chemistry computer programs
233:
13:
2321:
2046:
1997:
1545:
1437:Ciferri A, Perico A, eds. (2012).
1381:Compendium of Chemical Terminology
14:
2753:
68:Théorie de la figure de la Terre,
2498:
2492:
2486:
1801:. Oxford: Blackwell Scientific.
734:{\displaystyle \varepsilon _{r}}
707:{\displaystyle \varepsilon _{0}}
2246:
2204:
2154:
2096:
2069:
2053:Landau LD, Lifshitz EM (1960).
1958:
1917:
1858:
1815:
1603:
1499:Chemistry: A Molecular Approach
1329:Theory of Intermolecular Forces
1327:Margenau H, Kestner NR (1969).
1116:Effect on the behavior of gases
2742:Johannes Diderik van der Waals
1865:Savir Y, Tlusty T (May 2007).
1828:(6th ed.). New York, NY:
1777:Division of Chemical Education
1490:
1455:
1430:
1398:
1345:
1320:
1279:
1190:non-covalent interaction index
776:= distance between molecules.
714:= permittivity of free space,
327:
324:, both synthetic and natural.
1:
2061:. Oxford: Pergamon. pp.
1825:Molecular biology of the cell
1407:Essentials of Medical Geology
1273:
145:pressure, volume, temperature
1892:10.1371/journal.pone.0000468
765:{\displaystyle k_{\text{B}}}
7:
1951:10.1016/j.fluid.2023.113876
1797:Majer V, Svoboda V (1985).
1476:10.1021/acs.chemrev.5b00583
1415:10.1007/978-94-007-4375-5_7
1313:10.1016/j.fluid.2023.113876
1199:
1156:Quantum mechanical theories
1092:molecules interacting with
983:Relative strength of forces
945:{\displaystyle \alpha _{2}}
10:
2758:
2404:Metalâligand multiple bond
2010:Pure and Applied Chemistry
1159:
967:
772:= Boltzmann constant, and
687:= electric dipole moment,
511:
331:
237:
2668:
2645:
2576:
2538:
2518:
2507:
2484:
2467:
2449:
2340:
2329:
1262:Non-covalent interactions
1064:London dispersion forces
287:Hydrogen bonding in water
2267:10.1021/acs.jcim.9b01016
2132:10.1021/acs.jpca.9b09845
2023:10.1351/PAC-REC-10-01-02
804:the following equation:
1641:Theoretica Chimica Acta
1524:"Intermolecular Forces"
1394:10.1351/goldbook.H02899
1222:Force field (chemistry)
1122:Lennard-Jones potential
970:London dispersion force
958:London dispersion force
165:Lennard-Jones potential
124:London dispersion force
2232:10.1002/cphc.201701325
1983:10.1002/andp.202400115
1930:Fluid Phase Equilibria
1292:Fluid Phase Equilibria
1217:Coomber's relationship
1135:compressibility factor
946:
916:
766:
735:
708:
674:
459:
288:
226:, and is the basis of
2732:Intermolecular forces
1578:10.3390/ijms131012773
947:
917:
767:
736:
709:
675:
534:Willem Hendrik Keesom
460:
310:quaternary structures
286:
206:or a molecule with a
129:Cationâcation bonding
108:, ÏâÏ and ÏâÏ bonding
45:intramolecular forces
2394:Coordinate (dipolar)
1834:Taylor & Francis
1691:10.1039/TF9383401346
1232:Intramolecular force
998:Dissociation energy
929:
811:
749:
718:
691:
551:
508:Van der Waals forces
375:
192:electronic structure
161:Buckingham potential
112:Van der Waals forces
21:intermolecular force
2568:CâH···O interaction
2350:Electron deficiency
2182:2017PCCP...1917928L
2176:(27): 17928â17936.
2124:2020JPCA..124.1850K
2090:10.1021/ja00428a004
1942:2023FlPEq.57313876F
1883:2007PLoSO...2..468S
1779:. Purdue University
1718:1979Natur.278..332S
1571:(10): 12773â12856.
1304:2023FlPEq.57313876F
1252:van der Waals force
1181:perturbation theory
1173:van der Waals force
1108:, so important for
1106:enzymatic reactions
993:Dissociation energy
889:
874:
834:
634:
619:
589:
574:
514:van der Waals force
274:van der Waals radii
270:van der Waals force
212:enzymatic reactions
200:catalytic reactions
151:and intermolecular
149:virial coefficients
57:molecular mechanics
55:frequently used in
2553:Resonance-assisted
2190:10.1039/C7CP02110K
1971:Annalen der Physik
1773:"Lattice Energies"
1653:10.1007/BF00577166
1610:Keesom WH (1915).
1227:Hydrophobic effect
1188:chemistry, is the
1144:of the molecules.
952:= polarizability.
942:
912:
875:
860:
820:
762:
731:
704:
670:
620:
605:
575:
560:
530:Keesom interaction
498:hydration enthalpy
474:tetrachloromethane
455:
452:
432:
412:
392:
289:
2719:
2718:
2670:Electron counting
2641:
2640:
2530:London dispersion
2482:
2481:
2459:Metal aromaticity
2084:(12): 3415â3420.
1843:978-0-8153-4432-2
1808:978-0-632-01529-0
1758:978-0-618-31809-4
1712:(5702): 332â333.
1522:Blaber M (1996).
1508:978-0-321-65178-5
1448:978-0-470-52927-0
1424:978-94-007-4374-8
1338:978-0-08-016502-8
1185:quantum chemistry
1177:quantum mechanics
1077:
1076:
901:
798:Peter J. W. Debye
759:
659:
642:
453:
443:
433:
423:
413:
403:
393:
383:
358:hydrogen chloride
354:hydrogen chloride
298:group 16 hydrides
254:electronegativity
224:molecular biology
2749:
2737:Chemical bonding
2711:Jemmis mno rules
2563:Dihydrogen bonds
2516:
2515:
2502:
2496:
2490:
2424:Hyperconjugation
2338:
2337:
2316:
2309:
2302:
2293:
2292:
2287:
2286:
2250:
2244:
2243:
2217:
2208:
2202:
2201:
2167:
2158:
2152:
2151:
2118:(9): 1850â1860.
2109:
2100:
2094:
2093:
2073:
2067:
2066:
2060:
2050:
2044:
2043:
2025:
2016:(8): 1637â1641.
2001:
1995:
1994:
1962:
1956:
1955:
1953:
1921:
1915:
1914:
1904:
1894:
1862:
1856:
1855:
1819:
1813:
1812:
1794:
1788:
1787:
1785:
1784:
1769:
1763:
1762:
1744:
1738:
1737:
1726:10.1038/278332a0
1701:
1695:
1694:
1674:
1665:
1664:
1636:
1627:
1626:
1616:
1607:
1601:
1600:
1590:
1580:
1556:
1543:
1542:
1540:
1539:
1530:. Archived from
1519:
1513:
1512:
1494:
1488:
1487:
1470:(9): 5216â5300.
1464:Chemical Reviews
1459:
1453:
1452:
1434:
1428:
1427:
1402:
1396:
1373:
1367:
1366:
1364:
1363:
1349:
1343:
1342:
1324:
1318:
1317:
1315:
1283:
1169:hydrogen bonding
1110:living organisms
1086:covalent bonding
987:
986:
951:
949:
948:
943:
941:
940:
921:
919:
918:
913:
902:
900:
899:
898:
888:
883:
873:
868:
859:
858:
845:
844:
843:
833:
828:
815:
771:
769:
768:
763:
761:
760:
757:
740:
738:
737:
732:
730:
729:
713:
711:
710:
705:
703:
702:
679:
677:
676:
671:
660:
658:
657:
656:
644:
643:
640:
633:
628:
618:
613:
604:
603:
590:
588:
583:
573:
568:
555:
464:
462:
461:
456:
454:
444:
441:
439:
434:
424:
421:
419:
414:
404:
401:
399:
394:
384:
381:
379:
350:potential energy
234:Hydrogen bonding
98:Hydrogen bonding
2757:
2756:
2752:
2751:
2750:
2748:
2747:
2746:
2722:
2721:
2720:
2715:
2664:
2637:
2580:
2572:
2534:
2521:
2511:
2503:
2497:
2491:
2478:
2463:
2445:
2333:
2325:
2320:
2290:
2251:
2247:
2215:
2209:
2205:
2165:
2159:
2155:
2107:
2101:
2097:
2074:
2070:
2051:
2047:
2002:
1998:
1963:
1959:
1922:
1918:
1863:
1859:
1844:
1830:Garland Science
1820:
1816:
1809:
1795:
1791:
1782:
1780:
1771:
1770:
1766:
1759:
1747:EÄe SN (2004).
1745:
1741:
1702:
1698:
1675:
1668:
1637:
1630:
1614:
1608:
1604:
1557:
1546:
1537:
1535:
1520:
1516:
1509:
1495:
1491:
1460:
1456:
1449:
1435:
1431:
1425:
1403:
1399:
1374:
1370:
1361:
1359:
1351:
1350:
1346:
1339:
1325:
1321:
1284:
1280:
1276:
1271:
1237:Molecular solid
1202:
1164:
1158:
1118:
994:
985:
972:
966:
936:
932:
930:
927:
926:
894:
890:
884:
879:
869:
864:
854:
850:
846:
839:
835:
829:
824:
816:
814:
812:
809:
808:
782:
756:
752:
750:
747:
746:
745:= temperature,
725:
721:
719:
716:
715:
698:
694:
692:
689:
688:
652:
648:
639:
635:
629:
624:
614:
609:
599:
595:
591:
584:
579:
569:
564:
556:
554:
552:
549:
548:
525:
516:
510:
489:
440:
438:
420:
418:
400:
398:
380:
378:
376:
373:
372:
367:
345:
336:
330:
242:
236:
153:pair potentials
64:Alexis Clairaut
29:secondary force
17:
12:
11:
5:
2755:
2745:
2744:
2739:
2734:
2717:
2716:
2714:
2713:
2708:
2703:
2702:
2701:
2696:
2691:
2686:
2675:
2673:
2666:
2665:
2663:
2662:
2657:
2651:
2649:
2643:
2642:
2639:
2638:
2636:
2635:
2630:
2625:
2620:
2615:
2610:
2600:
2595:
2590:
2584:
2582:
2574:
2573:
2571:
2570:
2565:
2560:
2555:
2550:
2544:
2542:
2536:
2535:
2533:
2532:
2526:
2524:
2513:
2509:Intermolecular
2505:
2504:
2485:
2483:
2480:
2479:
2477:
2476:
2473:
2471:
2465:
2464:
2462:
2461:
2455:
2453:
2447:
2446:
2444:
2443:
2442:
2441:
2436:
2426:
2421:
2416:
2411:
2406:
2401:
2396:
2391:
2386:
2381:
2380:
2379:
2369:
2368:
2367:
2362:
2357:
2346:
2344:
2335:
2331:Intramolecular
2327:
2326:
2323:Chemical bonds
2319:
2318:
2311:
2304:
2296:
2289:
2288:
2261:(1): 268â278.
2245:
2226:(6): 724â735.
2203:
2153:
2095:
2068:
2045:
1996:
1957:
1916:
1857:
1842:
1814:
1807:
1789:
1764:
1757:
1739:
1696:
1666:
1647:(3): 249â257.
1628:
1602:
1544:
1528:mikeblaber.org
1514:
1507:
1497:Tro N (2011).
1489:
1454:
1447:
1429:
1423:
1397:
1368:
1357:global.oup.com
1344:
1337:
1319:
1277:
1275:
1272:
1270:
1269:
1264:
1259:
1254:
1249:
1244:
1239:
1234:
1229:
1224:
1219:
1214:
1209:
1203:
1201:
1198:
1160:Main article:
1157:
1154:
1142:thermal energy
1117:
1114:
1098:hydrogen bonds
1075:
1074:
1071:
1068:
1065:
1061:
1060:
1058:
1055:
1052:
1051:Dipoleâdipole
1048:
1047:
1044:
1041:
1038:
1032:
1031:
1029:
1026:
1023:
1022:Covalent bond
1019:
1018:
1016:
1013:
1010:
1009:Ionic lattice
1006:
1005:
1002:
996:
991:
984:
981:
968:Main article:
965:
962:
939:
935:
923:
922:
911:
908:
905:
897:
893:
887:
882:
878:
872:
867:
863:
857:
853:
849:
842:
838:
832:
827:
823:
819:
796:, named after
781:
778:
755:
728:
724:
701:
697:
681:
680:
669:
666:
663:
655:
651:
647:
638:
632:
627:
623:
617:
612:
608:
602:
598:
594:
587:
582:
578:
572:
567:
563:
559:
532:, named after
524:
521:
512:Main article:
509:
506:
488:
485:
478:carbon dioxide
466:
465:
451:
448:
437:
431:
428:
417:
411:
408:
397:
391:
388:
365:
344:
341:
332:Main article:
329:
326:
238:Main article:
235:
232:
184:molecular ions
155:, such as the
137:
136:
131:
126:
109:
103:
100:
15:
9:
6:
4:
3:
2:
2754:
2743:
2740:
2738:
2735:
2733:
2730:
2729:
2727:
2712:
2709:
2707:
2704:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2684:HĂŒckel's rule
2682:
2681:
2680:
2677:
2676:
2674:
2671:
2667:
2661:
2658:
2656:
2653:
2652:
2650:
2648:
2647:Bond cleavage
2644:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2613:Intercalation
2611:
2608:
2604:
2603:Metallophilic
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2585:
2583:
2579:
2575:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2545:
2543:
2541:
2537:
2531:
2528:
2527:
2525:
2523:
2520:Van der Waals
2517:
2514:
2510:
2506:
2501:
2495:
2489:
2475:
2474:
2472:
2470:
2466:
2460:
2457:
2456:
2454:
2452:
2448:
2440:
2437:
2435:
2432:
2431:
2430:
2427:
2425:
2422:
2420:
2417:
2415:
2412:
2410:
2407:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2378:
2375:
2374:
2373:
2370:
2366:
2363:
2361:
2358:
2356:
2353:
2352:
2351:
2348:
2347:
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2343:
2339:
2336:
2332:
2328:
2324:
2317:
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2298:
2297:
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2280:
2276:
2272:
2268:
2264:
2260:
2256:
2249:
2241:
2237:
2233:
2229:
2225:
2221:
2214:
2207:
2199:
2195:
2191:
2187:
2183:
2179:
2175:
2171:
2164:
2157:
2149:
2145:
2141:
2137:
2133:
2129:
2125:
2121:
2117:
2113:
2106:
2099:
2091:
2087:
2083:
2079:
2072:
2064:
2059:
2058:
2049:
2041:
2037:
2033:
2029:
2024:
2019:
2015:
2011:
2007:
2000:
1992:
1988:
1984:
1980:
1976:
1972:
1968:
1961:
1952:
1947:
1943:
1939:
1935:
1931:
1927:
1920:
1912:
1908:
1903:
1898:
1893:
1888:
1884:
1880:
1876:
1872:
1868:
1861:
1853:
1849:
1845:
1839:
1835:
1831:
1827:
1826:
1818:
1810:
1804:
1800:
1793:
1778:
1774:
1768:
1760:
1754:
1750:
1743:
1735:
1731:
1727:
1723:
1719:
1715:
1711:
1707:
1700:
1692:
1688:
1684:
1680:
1673:
1671:
1662:
1658:
1654:
1650:
1646:
1642:
1635:
1633:
1624:
1620:
1613:
1606:
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1594:
1589:
1584:
1579:
1574:
1570:
1566:
1562:
1555:
1553:
1551:
1549:
1534:on 2020-08-01
1533:
1529:
1525:
1518:
1510:
1504:
1500:
1493:
1485:
1481:
1477:
1473:
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1444:
1440:
1433:
1426:
1420:
1416:
1412:
1408:
1401:
1395:
1391:
1387:
1386:hydrogen bond
1383:
1382:
1377:
1372:
1358:
1354:
1348:
1340:
1334:
1330:
1323:
1314:
1309:
1305:
1301:
1297:
1293:
1289:
1282:
1278:
1268:
1265:
1263:
1260:
1258:
1255:
1253:
1250:
1248:
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1243:
1240:
1238:
1235:
1233:
1230:
1228:
1225:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1207:Ionic bonding
1205:
1204:
1197:
1193:
1191:
1186:
1182:
1178:
1174:
1170:
1163:
1153:
1149:
1147:
1143:
1138:
1136:
1131:
1127:
1123:
1113:
1111:
1107:
1103:
1102:covalent bond
1099:
1095:
1091:
1087:
1083:
1082:Ionic bonding
1072:
1069:
1066:
1063:
1062:
1059:
1056:
1053:
1050:
1049:
1045:
1042:
1039:
1037:
1036:Hydrogen bond
1034:
1033:
1030:
1027:
1024:
1021:
1020:
1017:
1014:
1011:
1008:
1007:
1003:
1001:
997:
992:
989:
988:
980:
978:
971:
961:
959:
953:
937:
933:
909:
906:
903:
895:
891:
885:
880:
876:
870:
865:
861:
855:
851:
847:
840:
836:
830:
825:
821:
817:
807:
806:
805:
801:
799:
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786:
777:
775:
753:
744:
726:
722:
699:
695:
686:
667:
664:
661:
653:
649:
645:
636:
630:
625:
621:
615:
610:
606:
600:
596:
592:
585:
580:
576:
570:
565:
561:
557:
547:
546:
545:
542:
537:
535:
531:
520:
515:
505:
501:
499:
493:
484:
481:
479:
475:
471:
470:dipole moment
449:
446:
435:
429:
426:
415:
409:
406:
395:
389:
386:
371:
370:
369:
363:
359:
355:
351:
340:
335:
325:
323:
319:
318:nucleic acids
315:
311:
307:
303:
299:
295:
285:
281:
279:
275:
271:
267:
263:
259:
255:
251:
247:
246:hydrogen bond
241:
240:Hydrogen bond
231:
229:
225:
221:
217:
213:
209:
205:
201:
197:
193:
189:
185:
181:
177:
173:
168:
166:
162:
158:
157:Mie potential
154:
150:
146:
142:
135:
132:
130:
127:
125:
121:
117:
113:
110:
107:
104:
101:
99:
96:
95:
94:
91:
89:
85:
81:
77:
73:
69:
65:
60:
58:
54:
50:
49:covalent bond
46:
42:
38:
34:
30:
26:
22:
2689:Baird's rule
2508:
2409:Charge-shift
2372:Hypervalence
2258:
2254:
2248:
2223:
2220:ChemPhysChem
2219:
2206:
2173:
2169:
2156:
2115:
2111:
2098:
2081:
2077:
2071:
2056:
2048:
2013:
2009:
1999:
1974:
1970:
1960:
1933:
1929:
1919:
1874:
1870:
1860:
1824:
1817:
1798:
1792:
1781:. Retrieved
1776:
1767:
1748:
1742:
1709:
1705:
1699:
1682:
1678:
1644:
1640:
1622:
1618:
1605:
1568:
1564:
1536:. Retrieved
1532:the original
1527:
1517:
1498:
1492:
1467:
1463:
1457:
1438:
1432:
1406:
1400:
1379:
1371:
1360:. Retrieved
1356:
1347:
1328:
1322:
1295:
1291:
1281:
1212:Salt bridges
1194:
1165:
1150:
1139:
1119:
1078:
1070:<4 to 63
1067:<1 to 15
999:
973:
954:
924:
802:
793:
790:polarization
787:
783:
773:
742:
684:
682:
538:
529:
526:
517:
502:
494:
490:
482:
467:
346:
337:
290:
245:
243:
220:biochemistry
169:
138:
116:Keesom force
92:
67:
61:
53:force fields
28:
24:
20:
18:
2679:Aromaticity
2655:Heterolysis
2633:Salt bridge
2578:Noncovalent
2548:Low-barrier
2429:Aromaticity
2419:Conjugation
2399:Pi backbond
1877:(5): e468.
1146:Temperature
1015:1100â20000
995:(kcal/mol)
794:Debye force
328:Salt bridge
120:Debye force
2726:Categories
2607:aurophilic
2588:Mechanical
1936:: 113876.
1783:2014-01-21
1625:: 636â646.
1538:2011-11-17
1362:2024-01-04
1298:: 113876.
1274:References
990:Bond type
362:chloroform
360:(HCl) and
256:, usually
228:enzymology
2699:spherical
2660:Homolysis
2623:Cationâpi
2598:Chalcogen
2558:Symmetric
2414:Hapticity
2283:209488458
2148:211070812
2032:1365-3075
1991:0003-3804
1852:887605755
1267:Solvation
1130:ideal gas
1094:substrate
1028:130â1100
1012:250â4000
1000:(kJ/mol)
934:α
877:ε
862:ε
852:π
837:α
818:−
723:ε
696:ε
622:ε
607:ε
597:π
558:−
450:−
447:δ
436:−
427:δ
416:⋯
410:−
407:δ
396:−
387:δ
302:secondary
216:substrate
196:enzymatic
172:molecules
141:viscosity
84:Boltzmann
2628:Anionâpi
2618:Stacking
2540:Hydrogen
2451:Metallic
2342:Covalent
2334:(strong)
2275:31877034
2240:29250908
2198:28664951
2140:32039597
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