897:. This is done by combining the valence bond covalent function with the functions describing all possible ionic structures or by combining the molecular orbital ground state function with the functions describing all possible excited states using unoccupied orbitals. It can then be seen that the simple molecular orbital approach overestimates the weight of the ionic structures while the simple valence bond approach neglects them. This can also be described as saying that the simple molecular orbital approach neglects
445:
3852:
652:
38:
575:
3846:
563:
1466:
803:), which are often described as electron deficient because there are not enough valence electrons to form localized (2-centre 2-electron) bonds joining all the atoms. However the more modern description using 3c–2e bonds does provide enough bonding orbitals to connect all the atoms, so that the molecules can instead be classified as electron-precise.
183:
2239:
522:. It is considered a "half bond" because it consists of only one shared electron (rather than two); in molecular orbital terms, the third electron is in an anti-bonding orbital which cancels out half of the bond formed by the other two electrons. Another example of a molecule containing a 3-electron bond, in addition to two 2-electron bonds, is
3858:
257:), four from the carbon itself and four from the hydrogens bonded to it. Each hydrogen has a valence of one and is surrounded by two electrons (a duet rule) – its own one electron plus one from the carbon. The numbers of electrons correspond to full shells in the quantum theory of the atom; the outer shell of a carbon atom is the
1182:
602:
is insufficient to explain the electron configuration in a molecule and its resulting experimentally-determined properties, hence a superposition of structures is needed. The same two atoms in such molecules can be bonded differently in different Lewis structures (a single bond in one, a double bond
885:
At the qualitative level, both theories contain incorrect predictions. Simple (Heitler–London) valence bond theory correctly predicts the dissociation of homonuclear diatomic molecules into separate atoms, while simple (Hartree–Fock) molecular orbital theory incorrectly predicts dissociation into a
908:
usually start from (but ultimately go far beyond) a molecular orbital rather than a valence bond approach, not because of any intrinsic superiority in the former but rather because the MO approach is more readily adapted to numerical computations. Molecular orbitals are orthogonal, which
2054:
1861:
is chosen in such a way that it encompasses all of the relevant bands participating in the bond. If the range to select is unclear, it can be identified in practice by examining the molecular orbitals that describe the electron density along with the considered bond.
1806:
865:
The two approaches are regarded as complementary, and each provides its own insights into the problem of chemical bonding. As valence bond theory builds the molecular wavefunction out of localized bonds, it is more suited for the calculation of
358:
structures and giant covalent structures. Individual molecules have strong bonds that hold the atoms together, but generally, there are negligible forces of attraction between molecules. Such covalent substances are usually gases, for example,
170:. Thus, covalent bonding does not necessarily require that the two atoms be of the same elements, only that they be of comparable electronegativity. Covalent bonding that entails the sharing of electrons over more than two atoms is said to be
252:
Lewis proposed that an atom forms enough covalent bonds to form a full (or closed) outer electron shell. In the diagram of methane shown here, the carbon atom has a valence of four and is, therefore, surrounded by eight electrons (the
1461:{\displaystyle cm^{\mathrm {A} }(n,l,m_{l},m_{s})={\frac {\int \limits _{E_{0}}\limits ^{E_{1}}Eg_{|n,l,m_{l},m_{s}\rangle }^{\mathrm {A} }(E)dE}{\int \limits _{E_{0}}\limits ^{E_{1}}g_{|n,l,m_{l},m_{s}\rangle }^{\mathrm {A} }(E)dE}}}
2436:
1940:
2329:
241:, in which valence electrons (those in the outer shell) are represented as dots around the atomic symbols. Pairs of electrons located between atoms represent covalent bonds. Multiple pairs represent multiple bonds, such as
92:, the sharing of electrons allows each atom to attain the equivalent of a full valence shell, corresponding to a stable electronic configuration. In organic chemistry, covalent bonding is much more common than
2943:
Heitler, W.; London, F. (1927). "Wechselwirkung neutraler Atome und homöopolare
Bindung nach der Quantenmechanik" [Interaction of neutral atoms and homeopolar bonds according to quantum mechanics].
2234:{\displaystyle C_{n_{\mathrm {A} }l_{\mathrm {A} },n_{\mathrm {B} }l_{\mathrm {B} }}=-\left|cm^{\mathrm {A} }(n_{\mathrm {A} },l_{\mathrm {A} })-cm^{\mathrm {B} }(n_{\mathrm {B} },l_{\mathrm {B} })\right|}
1552:
3344:
Dronskowski, Richard; Bloechl, Peter E. (2002-05-01). "Crystal orbital
Hamilton populations (COHP): energy-resolved visualization of chemical bonding in solids based on density-functional calculations".
330:
of the bond. Two atoms with equal electronegativity will make nonpolar covalent bonds such as H–H. An unequal relationship creates a polar covalent bond such as with H−Cl. However polarity also requires
2046:
1994:
2658:
1653:
917:
In COOP, COHP and BCOOP, evaluation of bond covalency is dependent on the basis set. To overcome this issue, an alternative formulation of the bond covalency can be provided in this way.
1052:
1612:
2480:
987:
2523:
2244:
where the contributions of the magnetic and spin quantum numbers are summed. According to this definition, the relative position of the A levels with respect to the B levels is
893:
Although the wavefunctions generated by both theories at the qualitative level do not agree and do not match the stabilization energy by experiment, they can be corrected by
4101:
3945:
479:. One-electron bonds often have about half the bond energy of a 2-electron bond, and are therefore called "half bonds". However, there are exceptions: in the case of
1172:
1139:
810:
atoms to each other in a banana shape, with a proton (the nucleus of a hydrogen atom) in the middle of the bond, sharing electrons with both boron atoms. In certain
1643:
723:, the electronegativity differences between different parts of the ring may dominate the chemical behavior of aromatic ring bonds, which otherwise are equivalent.
1106:
1080:
2555:
2354:
1857:
2597:
is exchanged. Therefore, covalent binding by quark interchange is expected to be the dominating mechanism of nuclear binding at small distance when the bound
2363:
4463:
4407:
3372:
Grechnev, Alexei; Ahuja, Rajeev; Eriksson, Olle (2003-01-01). "Balanced crystal orbital overlap population—a tool for analysing chemical bonds in solids".
1870:
2250:
850:
are filled with electrons first to produce a fully bonded valence configuration, followed by performing a linear combination of contributing structures (
3067:
Harcourt, Richard D., ed. (2015). "Chapter 2: Pauling "3-Electron Bonds", 4-Electron 3-Centre
Bonding, and the Need for an "Increased-Valence" Theory".
4063:
3990:
3671:
208:
549:
Molecules with odd-electron bonds are usually highly reactive. These types of bond are only stable between atoms with similar electronegativities.
4443:
3635:
615:
and each oxygen is a double bond in one structure and a single bond in the other two, so that the average bond order for each N–O interaction is
3317:
Hughbanks, Timothy; Hoffmann, Roald (2002-05-01). "Chains of trans-edge-sharing molybdenum octahedra: metal-metal bonding in extended systems".
3199:
Cammarata, Antonio; Rondinelli, James M. (21 September 2014). "Covalent dependence of octahedral rotations in orthorhombic perovskite oxides".
284:) in 1927. Their work was based on the valence bond model, which assumes that a chemical bond is formed when there is good overlap between the
4339:
4094:
3301:
3256:
2991:
2927:
2897:
855:
2567:
An analogous effect to covalent binding is believed to occur in some nuclear systems, with the difference that the shared fermions are
874:. As molecular orbital theory builds the molecular wavefunction out of delocalized orbitals, it is more suited for the calculation of
384:. In molecular structures, there are weak forces of attraction. Such covalent substances are low-boiling-temperature liquids (such as
2484:
the higher the overlap of the selected atomic bands, and thus the electron density described by those orbitals gives a more covalent
4132:
3644:
3280:
3076:
3051:
3026:
2760:
2731:
2702:
1474:
890:
of aromaticity, while simple valence bond theory incorrectly predicts that cyclobutadiene has larger resonance energy than benzene.
826:
After the development of quantum mechanics, two basic theories were proposed to provide a quantum description of chemical bonding:
3925:
396:). Macromolecular structures have large numbers of atoms linked by covalent bonds in chains, including synthetic polymers such as
4087:
3910:
1999:
1947:
4400:
3734:
750:
124:
3761:
3722:
3712:
3127:
784:
120:
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significantly increases the feasibility and speed of computer calculations compared to nonorthogonal valence bond orbitals.
4370:
3717:
815:
212:
article entitled "The
Arrangement of Electrons in Atoms and Molecules". Langmuir wrote that "we shall denote by the term
3664:
2627:
1801:{\displaystyle g(E)=\sum _{\mathrm {A} }\sum _{n,l}\sum _{m_{l},m_{s}}{g_{|n,l,m_{l},m_{s}\rangle }^{\mathrm {A} }(E)}}
249:. An alternative form of representation, not shown here, has bond-forming electron pairs represented as solid lines.
4393:
834:. A more recent quantum description is given in terms of atomic contributions to the electronic density of states.
428:). These substances have high melting and boiling points, are frequently brittle, and tend to have high electrical
261: = 2 shell, which can hold eight electrons, whereas the outer (and only) shell of a hydrogen atom is the
3985:
3980:
4499:
4478:
4360:
4344:
3970:
3960:
3935:
3905:
894:
272:
is needed to understand the nature of these bonds and predict the structures and properties of simple molecules.
31:
4319:
3751:
2621:
994:
831:
758:
701:
413:
1557:
436:, and the ability to form three or four electron pair bonds, often form such large macromolecular structures.
4012:
3915:
3887:
3657:
2582:
879:
3525:
Bashkanova, M.; Brodsky, S. J.; Clement, H. (2013). "Novel Six-Quark Hidden-Color
Dibaryon States in QCD".
745:
have higher co-ordination numbers than would be possible due to strictly covalent bonding according to the
299:(except for s orbitals) have specific directional properties leading to different types of covalent bonds.
843:
463:
species, which have an odd number of electrons. The simplest example of a 1-electron bond is found in the
303:
are the strongest covalent bonds and are due to head-on overlapping of orbitals on two different atoms. A
223:, who in 1916 described the sharing of electron pairs between atoms (and in 1926 he also coined the term "
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928:
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4274:
4056:
4017:
2673:
2643:
2493:
851:
847:
762:
593:
500:
4051:
3632:
268:
While the idea of shared electron pairs provides an effective qualitative picture of covalent bonding,
3069:
Bonding in
Electron-Rich Molecules: Qualitative Valence-Bond Approach via Increased-Valence Structures
2693:
Whitten, Kenneth W.; Gailey, Kenneth D.; Davis, Raymond E. (1992). "7-3 Formation of covalent bonds".
4245:
3975:
3866:
3729:
3688:
3544:
3491:
3436:
3381:
3208:
2953:
898:
732:
351:
171:
3596:
530:
can also be regarded as having two 3-electron bonds and one 2-electron bond, which accounts for its
4365:
4259:
3877:
3741:
3707:
3611:
2668:
827:
778:
766:
742:
705:
460:
166:
atoms share the two electrons via covalent bonding. Covalency is greatest between atoms of similar
144:
140:
112:
4041:
887:
673:
3796:
3560:
3534:
3460:
3405:
2969:
2861:
2590:
886:
mixture of atoms and ions. On the other hand, simple molecular orbital theory correctly predicts
871:
281:
3479:
3424:
2788:
444:
350:
There are several types of structures for covalent substances, including individual molecules,
4458:
4417:
4334:
4127:
4027:
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3452:
3397:
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3181:
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3018:
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2611:
905:
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811:
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327:
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269:
167:
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3808:
3781:
3552:
3499:
3444:
3389:
3354:
3326:
3216:
3173:
3013:
Stranks, D. R.; Heffernan, M. L.; Lee Dow, K. C.; McTigue, P. T.; Withers, G. R. A. (1970).
2961:
2853:
2822:
2663:
2572:
1147:
1114:
738:
535:
220:
108:
806:
Each such bond (2 per molecule in diborane) contains a pair of electrons which connect the
4473:
4284:
3920:
3791:
3639:
2775:
2633:
1619:
651:
599:
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448:
296:
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are credited with the first successful quantum mechanical explanation of a chemical bond (
229:
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191:
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3548:
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3440:
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indicates that quark interchange of either u or d quarks is the dominant process of the
1088:
1062:
416:(or giant covalent structures) contain large numbers of atoms linked in sheets (such as
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2749:
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273:
84:. The stable balance of attractive and repulsive forces between atoms, when they share
37:
3393:
2431:{\displaystyle C_{n_{\mathrm {A} }l_{\mathrm {A} },n_{\mathrm {B} }l_{\mathrm {B} }}.}
1816:
4493:
4240:
4235:
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4004:
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2648:
2586:
1935:{\displaystyle C_{n_{\mathrm {A} }l_{\mathrm {A} },n_{\mathrm {B} }l_{\mathrm {B} }}}
787:("3c–2e") three atoms share two electrons in bonding. This type of bonding occurs in
531:
93:
69:
61:
46:
3564:
2865:
2334:
where, for simplicity, we may omit the dependence from the principal quantum number
2324:{\displaystyle C_{\mathrm {A,B} }=-\left|cm^{\mathrm {A} }-cm^{\mathrm {B} }\right|}
753:("3c–4e") model which interprets the molecular wavefunction in terms of non-bonding
700: + 2 = 6). These occupy three delocalized π molecular orbitals (
186:
Early concepts in covalent bonding arose from this kind of image of the molecule of
4468:
3950:
3556:
716:
574:
543:
523:
507:
397:
277:
3448:
2981:
4428:
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exhibiting a greater stabilization than the hypothetical 1,3,5-cyclohexatriene.
663:
429:
316:
312:
304:
246:
242:
3845:
704:) or form conjugate π bonds in two resonance structures that linearly combine (
611:
ion is one such example with three equivalent structures. The bond between the
216:
the number of pairs of electrons that a given atom shares with its neighbors."
4183:
4167:
4157:
2653:
2616:
2579:
1811:
where the outer sum runs over all atoms A of the unit cell. The energy window
746:
604:
452:
300:
254:
100:
17:
3401:
4305:
3771:
3746:
854:) if there are several of them. In contrast, for molecular orbital theory a
754:
480:
335:
116:
65:
3228:
3185:
4079:
562:
4172:
792:
612:
417:
332:
163:
89:
85:
50:
3358:
3330:
3143:
Hofmann, K.; Prosenc, M. H.; Albert, B. R. (2007). "A new 4c–2e bond in
2857:
2826:
219:
The idea of covalent bonding can be traced several years before 1919 to
4162:
2965:
2598:
720:
709:
692:, the prototypical aromatic compound, there are 6 π bonding electrons (
689:
677:
608:
421:
405:
385:
378:
311:
are weaker and are due to lateral overlap between p (or d) orbitals. A
308:
187:
139:
etc.; thus a "co-valent bond", in essence, means that the atoms share "
104:
3511:
3456:
3220:
913:
Covalency from atomic contribution to the electronic density of states
3177:
2575:
2568:
425:
409:
389:
339:
224:
99:
Covalent bonding also includes many kinds of interactions, including
2841:
2810:
182:
3857:
506:
The simplest example of three-electron bonding can be found in the
3539:
2594:
807:
443:
401:
3649:
2722:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
315:
between two given atoms consists of one σ and one π bond, and a
73:
4389:
4083:
3653:
3614:. Department of Physics and Astronomy, Georgia State University
1547:{\displaystyle g_{|n,l,m_{l},m_{s}\rangle }^{\mathrm {A} }(E)}
360:
227:" for the smallest unit of radiant energy). He introduced the
603:
in another, or even none at all), resulting in a non-integer
137:
jointly, associated in action, partnered to a lesser degree,
688:
is an integer), it attains extra stability and symmetry. In
2697:(4th ed.). Saunders College Publishing. p. 264.
2041:{\displaystyle |n_{\mathrm {B} },l_{\mathrm {B} }\rangle }
1989:{\displaystyle |n_{\mathrm {A} },l_{\mathrm {A} }\rangle }
2535:
bond, which is specified in the same units of the energy
901:
while the simple valence bond approach overestimates it.
858:
is performed first, followed by filling of the resulting
2624:, also known as a dipolar bond or a dative covalent bond
2589:
at short distance. In particular, it dominates over the
1614:
of the atom A to the total electronic density of states
2811:"The Arrangement of Electrons in Atoms and Molecules"
2543:
2496:
2450:
2366:
2342:
2253:
2057:
2002:
1950:
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1656:
1622:
1560:
1477:
1185:
1150:
1117:
1091:
1065:
997:
931:
846:
of the molecule. For valence bond theory, the atomic
1996:
levels of atom A with respect to the mass center of
842:
The two theories represent two ways to build up the
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4293:
4267:
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4150:
4143:
4026:
4003:
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483:, the bond is actually stronger for the 1-electron
342:may cancel out, resulting in a non-polar molecule.
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459:Bonds with one or three electrons can be found in
3645:Structure and Bonding in Chemistry—Covalent Bonds
3122:. Cambridge University Press. pp. 275–306.
388:), and low-melting-temperature solids (such as
265: = 1 shell, which can hold only two.
202:in regard to bonding was first used in 1919 by
30:"Covalent" redirects here. For other uses, see
3599:. Department of Chemistry University of Oxford
499:. This exception can be explained in terms of
4401:
4095:
3665:
3251:. Oxford University Press. pp. 147–148.
2747:Gary L. Miessler; Donald Arthur Tarr (2004).
194:by indicating electrons shared between atoms.
8:
3480:"Using Nuclei to Probe Hadronization in QCD"
2983:Quantum Chemistry: Classic Scientific Papers
2442:In this formalism, the greater the value of
2035:
1983:
1776:
1601:
1523:
1428:
1325:
1038:
326:of the connected atoms which determines the
3021:: Melbourne University Press. p. 184.
672:, when a molecule with a planar ring obeys
4408:
4394:
4386:
4324:
4264:
4147:
4102:
4088:
4080:
3873:
3695:
3672:
3658:
3650:
3425:"Novel Features of Nuclear Chromodynamics"
3271:James D. Ingle Jr. and Stanley R. Crouch,
3090:
3088:
1554:is the contribution of the atomic orbital
27:Chemical bond by sharing of electron pairs
3538:
3242:
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1047:{\displaystyle |n,l,m_{l},m_{s}\rangle ,}
1032:
1019:
998:
996:
970:
957:
930:
88:, is known as covalent bonding. For many
4064:Polyhedral skeletal electron pair theory
3319:Journal of the American Chemical Society
2846:Journal of the American Chemical Society
2815:Journal of the American Chemical Society
1607:{\displaystyle |n,l,m_{l},m_{s}\rangle }
420:), or 3-dimensional structures (such as
322:Covalent bonds are also affected by the
209:Journal of the American Chemical Society
181:
36:
3478:Brodsky, S. J.; Mueller, A. H. (1988).
2685:
555:Modified Lewis structures with 3e bonds
3633:Covalent Bonds and Molecular Structure
3582:"Covalent bonding – Single bonds"
598:There are situations whereby a single
3597:"Electron Sharing and Covalent Bonds"
3103:. Cornell University Press. pp.
2659:Linear combination of atomic orbitals
856:linear combination of atomic orbitals
190:. Covalent bonding is implied in the
7:
3374:Journal of Physics: Condensed Matter
2913:
2911:
2909:
2883:
2881:
2879:
2877:
2875:
455:of an individual 2e bond and 3e bond
76:. These electron pairs are known as
2563:Analogous effect in nuclear systems
2475:{\displaystyle C_{\mathrm {A,B} },}
982:{\displaystyle cm(n,l,m_{l},m_{s})}
755:highest occupied molecular orbitals
546:also contain three-electron bonds.
2518:{\displaystyle C_{\mathrm {A,B} }}
2509:
2503:
2463:
2457:
2417:
2405:
2390:
2378:
2310:
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2187:
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2014:
1977:
1962:
1924:
1912:
1897:
1885:
1782:
1678:
1529:
1434:
1331:
1195:
25:
4133:Introduction to quantum mechanics
3347:The Journal of Physical Chemistry
3294:Modern Physical Organic Chemistry
3118:Weinhold, F.; Landis, C. (2005).
3042:Weinhold, F.; Landis, C. (2005).
2986:. World Scientific. p. 140.
2601:have covalence quarks in common.
3856:
3850:
3844:
2840:Lewis, Gilbert N. (1916-04-01).
838:Comparison of VB and MO theories
650:
573:
561:
534:and its formal bond order of 2.
125:three-center four-electron bonds
3429:The European Physical Journal A
3099:The Nature of the Chemical Bond
2809:Langmuir, Irving (1919-06-01).
2791:. Hyperphysics.phy-astr.gsu.edu
2778:– Collegiate Dictionary (2000).
785:three-center two-electron bonds
751:three-center four-electron bond
121:three-center two-electron bonds
3557:10.1016/j.physletb.2013.10.059
3249:Quanta: A Handbook of Concepts
3046:. Cambridge. pp. 96–100.
2223:
2193:
2172:
2142:
2004:
1952:
1846:
1820:
1794:
1788:
1737:
1666:
1660:
1632:
1626:
1562:
1541:
1535:
1484:
1446:
1440:
1389:
1343:
1337:
1286:
1239:
1201:
999:
976:
938:
822:Quantum mechanical description
816:four-center two-electron bonds
1:
2358:in the notation referring to
2048:levels of atom B is given as
832:molecular orbital (MO) theory
440:One- and three-electron bonds
64:that involves the sharing of
3504:10.1016/0370-2693(88)90719-8
3296:. University Science Books.
3015:Chemistry: A structural view
2628:Covalent bond classification
526:, NO. The oxygen molecule, O
131:dates from 1939. The prefix
3394:10.1088/0953-8984/15/45/014
3201:Journal of Chemical Physics
2842:"The atom and the molecule"
818:also have been postulated.
749:. This is explained by the
414:Network covalent structures
143:", such as is discussed in
4516:
3762:Metal–ligand multiple bond
3449:10.1140/epja/i2017-12234-5
776:
737:Certain molecules such as
730:
719:aromatics and substituted
661:
591:
538:and its heavier analogues
495:than for the 2-electron Li
432:. Elements that have high
404:, and biopolymers such as
319:is one σ and two π bonds.
29:
4479:List of organic compounds
4424:
4118:
3842:
2726:. John Wiley & Sons.
1176:for atom A is defined as
895:configuration interaction
880:spectral absorption bands
878:and the understanding of
870:and the understanding of
503:and inner-shell effects.
41:A covalent bond forming H
32:Covalent (disambiguation)
4320:Molecular orbital theory
3292:Anslyn, Eric V. (2006).
3273:Spectrochemical Analysis
2622:Coordinate covalent bond
828:valence bond (VB) theory
759:molecular orbital theory
702:molecular orbital theory
288:of participating atoms.
3423:Brodsky, S. J. (2017).
3275:, Prentice Hall, 1988,
3166:Chemical Communications
2978:English translation in
2922:(8 ed.). Pearson.
2892:(7 ed.). Pearson.
2571:rather than electrons.
904:Modern calculations in
292:Types of covalent bonds
3247:Atkins, P. W. (1974).
2946:Zeitschrift für Physik
2918:Bruice, Paula (2016).
2888:McMurry, John (2016).
2551:
2519:
2476:
2432:
2350:
2325:
2235:
2042:
1990:
1944:of the mass center of
1936:
1865:The relative position
1853:
1802:
1639:
1608:
1548:
1462:
1382:
1276:
1168:
1167:{\displaystyle m_{s},}
1135:
1134:{\displaystyle m_{l},}
1102:
1076:
1048:
983:
844:electron configuration
708:), creating a regular
684: + 2 (where
676:, where the number of
456:
195:
109:metal-to-metal bonding
53:
2718:March, Jerry (1992).
2674:Resonance (chemistry)
2552:
2520:
2477:
2433:
2351:
2326:
2236:
2043:
1991:
1937:
1854:
1803:
1640:
1609:
1549:
1463:
1354:
1248:
1169:
1136:
1103:
1077:
1049:
991:of an atomic orbital
984:
594:Resonance (chemistry)
447:
307:is usually a σ bond.
235:electron dot notation
185:
40:
3752:Coordinate (dipolar)
3095:Pauling, L. (1960).
2980:Hettema, H. (2000).
2541:
2494:
2448:
2364:
2340:
2251:
2055:
2000:
1948:
1871:
1817:
1654:
1638:{\displaystyle g(E)}
1620:
1558:
1475:
1183:
1148:
1115:
1089:
1063:
995:
929:
899:electron correlation
733:Hypervalent molecule
352:molecular structures
113:agostic interactions
4260:Valence bond theory
3926:C–H···O interaction
3708:Electron deficiency
3549:2013PhLB..727..438B
3496:1988PhLB..206..685B
3441:2017EPJA...53...48B
3386:2003JPCM...15.7751G
3359:10.1021/j100135a014
3331:10.1021/ja00349a027
3213:2014JChPh.141k4704C
3120:Valency and Bonding
3044:Valency and Bonding
2958:1927ZPhy...44..455H
2858:10.1021/ja02261a002
2827:10.1021/ja02227a002
2751:Inorganic Chemistry
2669:Noncovalent bonding
2488:bond. The quantity
1787:
1534:
1439:
1336:
876:ionization energies
872:reaction mechanisms
779:Electron deficiency
773:Electron deficiency
767:valence bond theory
743:sulfur hexafluoride
706:valence bond theory
346:Covalent structures
239:Lewis dot structure
168:electronegativities
145:valence bond theory
3911:Resonance-assisted
3638:2009-02-10 at the
2966:10.1007/bf01397394
2591:Yukawa interaction
2547:
2527:is denoted as the
2515:
2472:
2428:
2346:
2321:
2231:
2038:
1986:
1932:
1849:
1798:
1731:
1729:
1699:
1683:
1635:
1604:
1544:
1478:
1458:
1383:
1280:
1164:
1131:
1101:{\displaystyle l,}
1098:
1075:{\displaystyle n,}
1072:
1044:
979:
860:molecular orbitals
765:of sigma bonds in
457:
282:molecular hydrogen
196:
54:
45:(right) where two
4487:
4486:
4459:Organic synthesis
4454:Organic reactions
4449:Organic compounds
4439:Functional groups
4418:organic chemistry
4383:
4382:
4379:
4378:
4354:Constituent units
4335:Molecular orbital
4314:
4313:
4294:Constituent units
4254:
4253:
4128:Quantum mechanics
4077:
4076:
4028:Electron counting
3999:
3998:
3888:London dispersion
3840:
3839:
3817:Metal aromaticity
3584:. chemguide. 2000
3527:Physics Letters B
3484:Physics Letters B
3353:(33): 8617–8624.
3325:(11): 3528–3537.
3303:978-1-891389-31-3
3258:978-0-19-855493-6
3221:10.1063/1.4895967
3172:(29): 3097–3099.
2993:978-981-02-2771-5
2929:978-0-13-404228-2
2920:Organic Chemistry
2899:978-0-321-94317-0
2755:. Prentice Hall.
2695:General Chemistry
2630:(or LXZ notation)
2612:Bonding in solids
2550:{\displaystyle E}
2349:{\displaystyle n}
1700:
1684:
1672:
1456:
906:quantum chemistry
812:cluster compounds
696: = 1, 4
680:fit the formula 4
670:organic chemistry
465:dihydrogen cation
434:electronegativity
328:chemical polarity
324:electronegativity
270:quantum mechanics
16:(Redirected from
4507:
4500:Chemical bonding
4434:Covalent bonding
4410:
4403:
4396:
4387:
4325:
4265:
4246:Exchange-coupled
4148:
4111:Chemical bonding
4104:
4097:
4090:
4081:
4069:Jemmis mno rules
3921:Dihydrogen bonds
3874:
3860:
3854:
3848:
3782:Hyperconjugation
3696:
3674:
3667:
3660:
3651:
3622:
3620:
3619:
3612:"Chemical Bonds"
3607:
3605:
3604:
3592:
3590:
3589:
3569:
3568:
3542:
3522:
3516:
3515:
3475:
3469:
3468:
3420:
3414:
3413:
3369:
3363:
3362:
3341:
3335:
3334:
3314:
3308:
3307:
3289:
3283:
3269:
3263:
3262:
3244:
3233:
3232:
3196:
3190:
3189:
3178:10.1039/b704944g
3163:
3162:
3161:
3153:
3152:
3140:
3134:
3133:
3115:
3109:
3108:
3102:
3092:
3083:
3082:
3064:
3058:
3057:
3039:
3033:
3032:
3010:
3004:
3003:
3001:
3000:
2977:
2952:(6–7): 455–472.
2940:
2934:
2933:
2915:
2904:
2903:
2885:
2870:
2869:
2837:
2831:
2830:
2806:
2800:
2799:
2797:
2796:
2789:"Chemical Bonds"
2785:
2779:
2773:
2767:
2766:
2754:
2744:
2738:
2737:
2725:
2715:
2709:
2708:
2690:
2664:Metallic bonding
2558:
2556:
2554:
2553:
2548:
2534:
2526:
2524:
2522:
2521:
2516:
2514:
2513:
2512:
2487:
2483:
2481:
2479:
2478:
2473:
2468:
2467:
2466:
2439:
2437:
2435:
2434:
2429:
2424:
2423:
2422:
2421:
2420:
2410:
2409:
2408:
2395:
2394:
2393:
2383:
2382:
2381:
2357:
2355:
2353:
2352:
2347:
2330:
2328:
2327:
2322:
2320:
2316:
2315:
2314:
2313:
2297:
2296:
2295:
2271:
2270:
2269:
2240:
2238:
2237:
2232:
2230:
2226:
2222:
2221:
2220:
2207:
2206:
2205:
2192:
2191:
2190:
2171:
2170:
2169:
2156:
2155:
2154:
2141:
2140:
2139:
2115:
2114:
2113:
2112:
2111:
2101:
2100:
2099:
2086:
2085:
2084:
2074:
2073:
2072:
2047:
2045:
2044:
2039:
2034:
2033:
2032:
2019:
2018:
2017:
2007:
1995:
1993:
1992:
1987:
1982:
1981:
1980:
1967:
1966:
1965:
1955:
1943:
1941:
1939:
1938:
1933:
1931:
1930:
1929:
1928:
1927:
1917:
1916:
1915:
1902:
1901:
1900:
1890:
1889:
1888:
1860:
1858:
1856:
1855:
1852:{\displaystyle }
1850:
1845:
1844:
1832:
1831:
1807:
1805:
1804:
1799:
1797:
1786:
1785:
1779:
1775:
1774:
1762:
1761:
1740:
1728:
1727:
1726:
1714:
1713:
1698:
1682:
1681:
1646:
1644:
1642:
1641:
1636:
1613:
1611:
1610:
1605:
1600:
1599:
1587:
1586:
1565:
1553:
1551:
1550:
1545:
1533:
1532:
1526:
1522:
1521:
1509:
1508:
1487:
1467:
1465:
1464:
1459:
1457:
1455:
1438:
1437:
1431:
1427:
1426:
1414:
1413:
1392:
1381:
1380:
1379:
1369:
1368:
1367:
1352:
1335:
1334:
1328:
1324:
1323:
1311:
1310:
1289:
1275:
1274:
1273:
1263:
1262:
1261:
1246:
1238:
1237:
1225:
1224:
1200:
1199:
1198:
1175:
1173:
1171:
1170:
1165:
1160:
1159:
1142:
1140:
1138:
1137:
1132:
1127:
1126:
1109:
1107:
1105:
1104:
1099:
1083:
1081:
1079:
1078:
1073:
1053:
1051:
1050:
1045:
1037:
1036:
1024:
1023:
1002:
990:
988:
986:
985:
980:
975:
974:
962:
961:
862:with electrons.
739:xenon difluoride
654:
646:
644:
643:
640:
637:
630:
628:
627:
624:
621:
577:
565:
536:Chlorine dioxide
521:
520:
519:
494:
493:
492:
478:
477:
476:
221:Gilbert N. Lewis
161:
160:
159:
150:In the molecule
21:
4515:
4514:
4510:
4509:
4508:
4506:
4505:
4504:
4490:
4489:
4488:
4483:
4474:Stereochemistry
4420:
4414:
4384:
4375:
4349:
4310:
4289:
4285:Lewis structure
4250:
4221:
4177:
4139:
4114:
4108:
4078:
4073:
4022:
3995:
3938:
3930:
3892:
3879:
3869:
3861:
3855:
3849:
3836:
3821:
3803:
3691:
3683:
3678:
3640:Wayback Machine
3629:
3617:
3615:
3610:
3602:
3600:
3595:
3587:
3585:
3580:
3577:
3572:
3524:
3523:
3519:
3477:
3476:
3472:
3422:
3421:
3417:
3371:
3370:
3366:
3343:
3342:
3338:
3316:
3315:
3311:
3304:
3291:
3290:
3286:
3270:
3266:
3259:
3246:
3245:
3236:
3198:
3197:
3193:
3160:
3157:
3156:
3155:
3151:
3148:
3147:
3146:
3144:
3142:
3141:
3137:
3130:
3117:
3116:
3112:
3094:
3093:
3086:
3079:
3066:
3065:
3061:
3054:
3041:
3040:
3036:
3029:
3012:
3011:
3007:
2998:
2996:
2994:
2979:
2942:
2941:
2937:
2930:
2917:
2916:
2907:
2900:
2887:
2886:
2873:
2839:
2838:
2834:
2808:
2807:
2803:
2794:
2792:
2787:
2786:
2782:
2776:Merriam-Webster
2774:
2770:
2763:
2746:
2745:
2741:
2734:
2717:
2716:
2712:
2705:
2692:
2691:
2687:
2683:
2678:
2634:Covalent radius
2607:
2565:
2539:
2538:
2536:
2532:
2497:
2492:
2491:
2489:
2485:
2451:
2446:
2445:
2443:
2411:
2399:
2384:
2372:
2367:
2362:
2361:
2359:
2338:
2337:
2335:
2304:
2286:
2282:
2278:
2254:
2249:
2248:
2211:
2196:
2181:
2160:
2145:
2130:
2126:
2122:
2102:
2090:
2075:
2063:
2058:
2053:
2052:
2023:
2008:
1998:
1997:
1971:
1956:
1946:
1945:
1918:
1906:
1891:
1879:
1874:
1869:
1868:
1866:
1836:
1823:
1815:
1814:
1812:
1766:
1753:
1718:
1705:
1652:
1651:
1618:
1617:
1615:
1591:
1578:
1556:
1555:
1513:
1500:
1473:
1472:
1418:
1405:
1371:
1359:
1353:
1315:
1302:
1265:
1253:
1247:
1229:
1216:
1189:
1181:
1180:
1151:
1146:
1145:
1143:
1118:
1113:
1112:
1110:
1087:
1086:
1084:
1061:
1060:
1058:
1056:quantum numbers
1028:
1015:
993:
992:
966:
953:
927:
926:
924:
915:
848:hybrid orbitals
840:
824:
802:
798:
781:
775:
735:
729:
715:In the case of
666:
660:
641:
638:
635:
634:
632:
625:
622:
619:
618:
616:
600:Lewis structure
596:
590:
585:
584:
583:
582:
581:
578:
570:
569:
566:
557:
556:
540:bromine dioxide
529:
518:
515:
514:
513:
511:
498:
491:
488:
487:
486:
484:
475:
472:
471:
470:
468:
442:
395:
382:
375:
368:
348:
301:Sigma (σ) bonds
297:Atomic orbitals
294:
286:atomic orbitals
204:Irving Langmuir
192:Lewis structure
180:
158:
155:
154:
153:
151:
44:
35:
28:
23:
22:
15:
12:
11:
5:
4513:
4511:
4503:
4502:
4492:
4491:
4485:
4484:
4482:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4431:
4425:
4422:
4421:
4415:
4413:
4412:
4405:
4398:
4390:
4381:
4380:
4377:
4376:
4374:
4373:
4371:Antibonding MO
4368:
4366:Non-bonding MO
4363:
4357:
4355:
4351:
4350:
4348:
4347:
4342:
4337:
4331:
4329:
4322:
4316:
4315:
4312:
4311:
4309:
4308:
4303:
4297:
4295:
4291:
4290:
4288:
4287:
4282:
4277:
4275:Hybrid orbital
4271:
4269:
4262:
4256:
4255:
4252:
4251:
4249:
4248:
4243:
4238:
4232:
4230:
4223:
4222:
4220:
4219:
4214:
4209:
4204:
4199:
4194:
4188:
4186:
4179:
4178:
4176:
4175:
4170:
4165:
4160:
4154:
4152:
4145:
4144:Types of bonds
4141:
4140:
4138:
4137:
4136:
4135:
4125:
4123:Atomic orbital
4119:
4116:
4115:
4109:
4107:
4106:
4099:
4092:
4084:
4075:
4074:
4072:
4071:
4066:
4061:
4060:
4059:
4054:
4049:
4044:
4033:
4031:
4024:
4023:
4021:
4020:
4015:
4009:
4007:
4001:
4000:
3997:
3996:
3994:
3993:
3988:
3983:
3978:
3973:
3968:
3958:
3953:
3948:
3942:
3940:
3932:
3931:
3929:
3928:
3923:
3918:
3913:
3908:
3902:
3900:
3894:
3893:
3891:
3890:
3884:
3882:
3871:
3867:Intermolecular
3863:
3862:
3843:
3841:
3838:
3837:
3835:
3834:
3831:
3829:
3823:
3822:
3820:
3819:
3813:
3811:
3805:
3804:
3802:
3801:
3800:
3799:
3794:
3784:
3779:
3774:
3769:
3764:
3759:
3754:
3749:
3744:
3739:
3738:
3737:
3727:
3726:
3725:
3720:
3715:
3704:
3702:
3693:
3689:Intramolecular
3685:
3684:
3681:Chemical bonds
3679:
3677:
3676:
3669:
3662:
3654:
3648:
3647:
3642:
3628:
3627:External links
3625:
3624:
3623:
3608:
3593:
3576:
3573:
3571:
3570:
3517:
3470:
3415:
3364:
3336:
3309:
3302:
3284:
3264:
3257:
3234:
3207:(11): 114704.
3191:
3158:
3149:
3135:
3128:
3110:
3084:
3077:
3059:
3052:
3034:
3027:
3005:
2992:
2935:
2928:
2905:
2898:
2871:
2852:(4): 762–785.
2832:
2821:(6): 868–934.
2801:
2780:
2768:
2761:
2739:
2732:
2710:
2703:
2684:
2682:
2679:
2677:
2676:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2639:Disulfide bond
2636:
2631:
2625:
2619:
2614:
2608:
2606:
2603:
2564:
2561:
2546:
2511:
2508:
2505:
2500:
2471:
2465:
2462:
2459:
2454:
2427:
2419:
2414:
2407:
2402:
2398:
2392:
2387:
2380:
2375:
2370:
2345:
2332:
2331:
2319:
2312:
2307:
2303:
2300:
2294:
2289:
2285:
2281:
2277:
2274:
2268:
2265:
2262:
2257:
2242:
2241:
2229:
2225:
2219:
2214:
2210:
2204:
2199:
2195:
2189:
2184:
2180:
2177:
2174:
2168:
2163:
2159:
2153:
2148:
2144:
2138:
2133:
2129:
2125:
2121:
2118:
2110:
2105:
2098:
2093:
2089:
2083:
2078:
2071:
2066:
2061:
2037:
2031:
2026:
2022:
2016:
2011:
2006:
1985:
1979:
1974:
1970:
1964:
1959:
1954:
1926:
1921:
1914:
1909:
1905:
1899:
1894:
1887:
1882:
1877:
1848:
1843:
1839:
1835:
1830:
1826:
1822:
1809:
1808:
1796:
1793:
1790:
1784:
1778:
1773:
1769:
1765:
1760:
1756:
1752:
1749:
1746:
1743:
1739:
1734:
1725:
1721:
1717:
1712:
1708:
1703:
1697:
1694:
1691:
1687:
1680:
1675:
1671:
1668:
1665:
1662:
1659:
1634:
1631:
1628:
1625:
1603:
1598:
1594:
1590:
1585:
1581:
1577:
1574:
1571:
1568:
1564:
1543:
1540:
1537:
1531:
1525:
1520:
1516:
1512:
1507:
1503:
1499:
1496:
1493:
1490:
1486:
1481:
1469:
1468:
1454:
1451:
1448:
1445:
1442:
1436:
1430:
1425:
1421:
1417:
1412:
1408:
1404:
1401:
1398:
1395:
1391:
1386:
1378:
1374:
1366:
1362:
1357:
1351:
1348:
1345:
1342:
1339:
1333:
1327:
1322:
1318:
1314:
1309:
1305:
1301:
1298:
1295:
1292:
1288:
1283:
1279:
1272:
1268:
1260:
1256:
1251:
1244:
1241:
1236:
1232:
1228:
1223:
1219:
1215:
1212:
1209:
1206:
1203:
1197:
1192:
1188:
1163:
1158:
1154:
1130:
1125:
1121:
1097:
1094:
1071:
1068:
1043:
1040:
1035:
1031:
1027:
1022:
1018:
1014:
1011:
1008:
1005:
1001:
978:
973:
969:
965:
960:
956:
952:
949:
946:
943:
940:
937:
934:
914:
911:
839:
836:
823:
820:
800:
796:
789:boron hydrides
777:Main article:
774:
771:
731:Main article:
728:
725:
662:Main article:
659:
656:
592:Main article:
589:
586:
579:
572:
571:
567:
560:
559:
558:
554:
553:
552:
551:
544:iodine dioxide
527:
516:
496:
489:
473:
441:
438:
393:
380:
373:
366:
356:macromolecular
347:
344:
293:
290:
274:Walter Heitler
230:Lewis notation
179:
176:
156:
70:electron pairs
49:share the two
47:hydrogen atoms
42:
26:
24:
18:Covalent bonds
14:
13:
10:
9:
6:
4:
3:
2:
4512:
4501:
4498:
4497:
4495:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4426:
4423:
4419:
4411:
4406:
4404:
4399:
4397:
4392:
4391:
4388:
4372:
4369:
4367:
4364:
4362:
4359:
4358:
4356:
4352:
4346:
4343:
4341:
4338:
4336:
4333:
4332:
4330:
4326:
4323:
4321:
4317:
4307:
4304:
4302:
4301:Covalent bond
4299:
4298:
4296:
4292:
4286:
4283:
4281:
4278:
4276:
4273:
4272:
4270:
4266:
4263:
4261:
4257:
4247:
4244:
4242:
4239:
4237:
4234:
4233:
4231:
4229:
4224:
4218:
4215:
4213:
4212:5 (quintuple)
4210:
4208:
4207:4 (quadruple)
4205:
4203:
4200:
4198:
4195:
4193:
4190:
4189:
4187:
4185:
4180:
4174:
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4155:
4153:
4149:
4146:
4142:
4134:
4131:
4130:
4129:
4126:
4124:
4121:
4120:
4117:
4112:
4105:
4100:
4098:
4093:
4091:
4086:
4085:
4082:
4070:
4067:
4065:
4062:
4058:
4055:
4053:
4050:
4048:
4045:
4043:
4042:Hückel's rule
4040:
4039:
4038:
4035:
4034:
4032:
4029:
4025:
4019:
4016:
4014:
4011:
4010:
4008:
4006:
4005:Bond cleavage
4002:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3971:Intercalation
3969:
3966:
3962:
3961:Metallophilic
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3943:
3941:
3937:
3933:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3907:
3904:
3903:
3901:
3899:
3895:
3889:
3886:
3885:
3883:
3881:
3878:Van der Waals
3875:
3872:
3868:
3864:
3859:
3853:
3847:
3833:
3832:
3830:
3828:
3824:
3818:
3815:
3814:
3812:
3810:
3806:
3798:
3795:
3793:
3790:
3789:
3788:
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3736:
3733:
3732:
3731:
3728:
3724:
3721:
3719:
3716:
3714:
3711:
3710:
3709:
3706:
3705:
3703:
3701:
3697:
3694:
3690:
3686:
3682:
3675:
3670:
3668:
3663:
3661:
3656:
3655:
3652:
3646:
3643:
3641:
3637:
3634:
3631:
3630:
3626:
3613:
3609:
3598:
3594:
3583:
3579:
3578:
3574:
3566:
3562:
3558:
3554:
3550:
3546:
3541:
3536:
3532:
3528:
3521:
3518:
3513:
3509:
3505:
3501:
3497:
3493:
3489:
3485:
3481:
3474:
3471:
3466:
3462:
3458:
3454:
3450:
3446:
3442:
3438:
3434:
3430:
3426:
3419:
3416:
3411:
3407:
3403:
3399:
3395:
3391:
3387:
3383:
3379:
3375:
3368:
3365:
3360:
3356:
3352:
3348:
3340:
3337:
3332:
3328:
3324:
3320:
3313:
3310:
3305:
3299:
3295:
3288:
3285:
3282:
3281:0-13-826876-2
3278:
3274:
3268:
3265:
3260:
3254:
3250:
3243:
3241:
3239:
3235:
3230:
3226:
3222:
3218:
3214:
3210:
3206:
3202:
3195:
3192:
3187:
3183:
3179:
3175:
3171:
3167:
3139:
3136:
3131:
3125:
3121:
3114:
3111:
3106:
3101:
3100:
3091:
3089:
3085:
3080:
3078:9783319166766
3074:
3070:
3063:
3060:
3055:
3053:0-521-83128-8
3049:
3045:
3038:
3035:
3030:
3028:0-522-83988-6
3024:
3020:
3019:Carlton, Vic.
3016:
3009:
3006:
2995:
2989:
2985:
2984:
2975:
2971:
2967:
2963:
2959:
2955:
2951:
2947:
2939:
2936:
2931:
2925:
2921:
2914:
2912:
2910:
2906:
2901:
2895:
2891:
2884:
2882:
2880:
2878:
2876:
2872:
2867:
2863:
2859:
2855:
2851:
2847:
2843:
2836:
2833:
2828:
2824:
2820:
2816:
2812:
2805:
2802:
2790:
2784:
2781:
2777:
2772:
2769:
2764:
2762:0-13-035471-6
2758:
2753:
2752:
2743:
2740:
2735:
2733:0-471-60180-2
2729:
2724:
2723:
2714:
2711:
2706:
2704:0-03-072373-6
2700:
2696:
2689:
2686:
2680:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2649:Hydrogen bond
2647:
2645:
2644:Hybridization
2642:
2640:
2637:
2635:
2632:
2629:
2626:
2623:
2620:
2618:
2615:
2613:
2610:
2609:
2604:
2602:
2600:
2596:
2592:
2588:
2587:nuclear force
2584:
2583:cross-section
2581:
2577:
2574:
2570:
2562:
2560:
2544:
2530:
2506:
2498:
2469:
2460:
2452:
2440:
2425:
2412:
2400:
2396:
2385:
2373:
2368:
2343:
2317:
2305:
2301:
2298:
2287:
2283:
2279:
2275:
2272:
2263:
2255:
2247:
2246:
2245:
2227:
2212:
2208:
2197:
2182:
2178:
2175:
2161:
2157:
2146:
2131:
2127:
2123:
2119:
2116:
2103:
2091:
2087:
2076:
2064:
2059:
2051:
2050:
2049:
2024:
2020:
2009:
1972:
1968:
1957:
1919:
1907:
1903:
1892:
1880:
1875:
1863:
1841:
1837:
1833:
1828:
1824:
1791:
1771:
1767:
1763:
1758:
1754:
1750:
1747:
1744:
1741:
1732:
1723:
1719:
1715:
1710:
1706:
1701:
1695:
1692:
1689:
1685:
1673:
1669:
1663:
1657:
1650:
1649:
1648:
1647:of the solid
1629:
1623:
1596:
1592:
1588:
1583:
1579:
1575:
1572:
1569:
1566:
1538:
1518:
1514:
1510:
1505:
1501:
1497:
1494:
1491:
1488:
1479:
1452:
1449:
1443:
1423:
1419:
1415:
1410:
1406:
1402:
1399:
1396:
1393:
1384:
1376:
1372:
1364:
1360:
1355:
1349:
1346:
1340:
1320:
1316:
1312:
1307:
1303:
1299:
1296:
1293:
1290:
1281:
1277:
1270:
1266:
1258:
1254:
1249:
1242:
1234:
1230:
1226:
1221:
1217:
1213:
1210:
1207:
1204:
1190:
1186:
1179:
1178:
1177:
1161:
1156:
1152:
1128:
1123:
1119:
1095:
1092:
1069:
1066:
1057:
1041:
1033:
1029:
1025:
1020:
1016:
1012:
1009:
1006:
1003:
971:
967:
963:
958:
954:
950:
947:
944:
941:
935:
932:
923:
918:
912:
910:
907:
902:
900:
896:
891:
889:
888:Hückel's rule
883:
881:
877:
873:
869:
868:bond energies
863:
861:
857:
853:
849:
845:
837:
835:
833:
829:
821:
819:
817:
813:
809:
804:
794:
790:
786:
780:
772:
770:
768:
764:
760:
756:
752:
748:
744:
740:
734:
726:
724:
722:
718:
713:
711:
707:
703:
699:
695:
691:
687:
683:
679:
675:
674:Hückel's rule
671:
665:
657:
655:
653:
648:
614:
610:
606:
601:
595:
587:
576:
564:
550:
547:
545:
541:
537:
533:
532:paramagnetism
525:
509:
504:
502:
501:hybridization
482:
466:
462:
454:
450:
446:
439:
437:
435:
431:
427:
423:
419:
415:
411:
407:
403:
399:
391:
387:
383:
376:
369:
362:
357:
353:
345:
343:
341:
337:
334:
329:
325:
320:
318:
314:
310:
306:
302:
298:
291:
289:
287:
283:
279:
275:
271:
266:
264:
260:
256:
250:
248:
244:
240:
236:
232:
231:
226:
222:
217:
215:
211:
210:
205:
201:
193:
189:
184:
177:
175:
173:
169:
165:
148:
146:
142:
138:
134:
130:
129:covalent bond
126:
122:
118:
114:
110:
106:
102:
97:
95:
94:ionic bonding
91:
87:
83:
82:bonding pairs
79:
75:
71:
67:
63:
62:chemical bond
59:
58:covalent bond
52:
48:
39:
33:
19:
4469:Spectroscopy
4464:Publications
4444:Nomenclature
4433:
4416:Concepts in
4300:
4217:6 (sextuple)
4184:multiplicity
4047:Baird's rule
3767:Charge-shift
3730:Hypervalence
3699:
3616:. Retrieved
3601:. Retrieved
3586:. Retrieved
3533:(4–5): 438.
3530:
3526:
3520:
3487:
3483:
3473:
3432:
3428:
3418:
3380:(45): 7751.
3377:
3373:
3367:
3350:
3346:
3339:
3322:
3318:
3312:
3293:
3287:
3272:
3267:
3248:
3204:
3200:
3194:
3169:
3165:
3138:
3119:
3113:
3098:
3071:. Springer.
3068:
3062:
3043:
3037:
3014:
3008:
2997:. Retrieved
2982:
2949:
2945:
2938:
2919:
2889:
2849:
2845:
2835:
2818:
2814:
2804:
2793:. Retrieved
2783:
2771:
2750:
2742:
2721:
2713:
2694:
2688:
2566:
2528:
2441:
2333:
2243:
1864:
1810:
1470:
919:
916:
903:
892:
884:
864:
841:
825:
814:, so-called
805:
782:
736:
727:Hypervalence
717:heterocyclic
714:
697:
693:
685:
681:
667:
649:
597:
568:Nitric oxide
548:
524:nitric oxide
508:helium dimer
505:
458:
398:polyethylene
392:and solid CO
349:
321:
309:Pi (π) bonds
295:
278:Fritz London
267:
262:
258:
251:
247:triple bonds
243:double bonds
238:
234:
228:
218:
213:
207:
199:
197:
149:
136:
132:
128:
98:
81:
78:shared pairs
77:
57:
55:
4429:Aromaticity
4151:By symmetry
4037:Aromaticity
4013:Heterolysis
3991:Salt bridge
3936:Noncovalent
3906:Low-barrier
3787:Aromaticity
3777:Conjugation
3757:Pi backbond
2573:High energy
922:mass center
678:π electrons
664:Aromaticity
658:Aromaticity
453:MO diagrams
430:resistivity
317:triple bond
313:double bond
305:single bond
172:delocalized
127:. The term
4361:Bonding MO
4345:MO diagram
4202:3 (triple)
4197:2 (double)
4192:1 (single)
3965:aurophilic
3946:Mechanical
3618:2012-02-05
3603:2012-02-05
3588:2012-02-05
3490:(4): 685.
3129:0521831288
2999:2012-02-05
2795:2013-06-09
2681:References
2654:Ionic bond
2617:Bond order
2580:scattering
747:octet rule
605:bond order
338:, or else
255:octet rule
117:bent bonds
4306:Lone pair
4280:Resonance
4168:Delta (δ)
4158:Sigma (σ)
4057:spherical
4018:Homolysis
3981:Cation–pi
3956:Chalcogen
3916:Symmetric
3772:Hapticity
3540:1308.6404
3465:126305939
3435:(3): 48.
3410:250757642
3402:0953-8984
2974:119739102
2890:Chemistry
2529:covalency
2299:−
2276:−
2176:−
2120:−
2036:⟩
1984:⟩
1777:⟩
1702:∑
1686:∑
1674:∑
1602:⟩
1524:⟩
1429:⟩
1356:∫
1326:⟩
1250:∫
1039:⟩
852:resonance
763:resonance
620:2 + 1 + 1
588:Resonance
481:dilithium
336:asymmetry
333:geometric
214:covalence
200:covalence
198:The term
105:π-bonding
101:σ-bonding
90:molecules
86:electrons
66:electrons
51:electrons
4494:Category
4328:Concepts
4268:Concepts
3986:Anion–pi
3976:Stacking
3898:Hydrogen
3809:Metallic
3700:Covalent
3692:(strong)
3636:Archived
3565:30153514
3229:25240365
3186:17639154
2866:95865413
2605:See also
2593:where a
2578:-proton
793:diborane
791:such as
721:benzenes
613:nitrogen
580:Dioxygen
510:cation,
418:graphite
406:proteins
164:hydrogen
72:between
68:to form
4241:Singlet
4236:Triplet
4173:Phi (φ)
3951:Halogen
3797:bicyclo
3742:Agostic
3575:Sources
3545:Bibcode
3512:1448604
3492:Bibcode
3457:1341388
3437:Bibcode
3382:Bibcode
3209:Bibcode
3105:340–354
2954:Bibcode
2599:hadrons
2557:
2537:
2531:of the
2525:
2490:
2482:
2444:
2438:
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