482:
389:
499:
2418:
470:
104:
266:
2412:
2424:
481:
2178:
The electrostatic interaction between the Br atom of the inhibitor and the OG of Thr 113 has an unusually short distance of 2.973(4) Ă
. The short contact between Br and Thr 113 OG explains the selectivity of IDD 594 towards AR, because in aldehyde reductase the Thr residue is
1928:
Corradi E, Meille SV, Messina MT, Metrangolo P, Resnati G (May 2000). "Halogen
Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes Perfluorocarbon-hydrocarbon self-assembly, part IX. This work was supported by MURST (Cofinanziamento '99) and EU (COST-D12-0012)". Communications.
305:
and bromine atoms, much closer than the sum (3.35 Ă
) of the atoms' van der Waals radii; and that the angle between the O−Br and Br−Br bond was about 180°. From these facts, Hassel concluded that halogen atoms are directly linked to electron pair donors in a direction with a bond
286:'s theory of inner-sphere and outer-sphere interactions. In Mulliken's categorization, the intermolecular interactions associated with small partial charges affect only the "inner sphere" of an atom's electron distribution; the electron redistribution associated with
359:
In 2007, computational calculations by
Politzer and Murray showed that an anisotropic electron density distribution around the halogen nucleus â the "Ï-hole" â underlay the high directionality of the halogen bond. This hole was then experimentally observed using
1111:
Aragoni MC, Arca M, Demartin F, Devillanova FA, Garau A, Isaia F, et al. (July 2005). "DFT calculations, structural and spectroscopic studies on the products formed between IBr and N,N'-dimethylbenzoimidazole-2(3H)-thione and -2(3H)-selone".
487:
Post-polymerization crystal structure: the oxygen atom (purple) forms a hydrogen bond (blue dashed line) and a weak halogen bond with the polymer's iodine substituents. Iodine may also form a halogen bond with the terminal nitriles (red dashed
130:; the electron concentration associated with that bond leaves a positively charged "hole" on the other side. Although all halogens can theoretically participate in halogen bonds, the Ï-hole shrinks if the electron cloud in question
2179:
replaced by Tyr....The IDD 594-Br/Thr 113-OG interaction also contributes to the potency of the inhibitor. Other halogens, such as chlorine, cannot engage in a similar interaction (due to its lower polarizability).
273:
In 1814, Jean-Jacques Colin discovered (to his surprise) that a mixture of dry gaseous ammonia and iodine formed a shiny, metallic-appearing liquid. Frederick
Guthrie established the precise composition of the resulting
459:. The underlying mechanism is a self-organization of the amides via hydrogen bonds that then transfers to the diiododiacetylene monomers via halogen bonds. Although pure diiododiacetylene crystals do not
1640:
Mallada B, Gallardo A, Lamanec M, de la Torre B, Ć pirko V, Hobza P, Jelinek P (November 2021). "Real-space imaging of anisotropic charge of Ï-hole by means of Kelvin probe force microscopy".
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Clark T, Hennemann M, Murray JS, Politzer P (February 2007). "Halogen bonding: the sigma-hole. Proceedings of "Modeling interactions in biomolecules II", Prague, September 5th-9th, 2005".
1543:
Dumas JM, Peurichard H, Gomel M (1978). "CX4...Base
Interactions as Models of Weak Charge-transfer Interactions: Comparison with Strong Charge-transfer and Hydrogen-bond Interactions".
1562:
Legon AC (September 1999). "Prereactive
Complexes of Dihalogens XY with Lewis Bases B in the Gas Phase: A Systematic Case for the Halogen Analogue B···XY of the Hydrogen Bond B···HX".
510:
Most biological macromolecules contain few or no halogen atoms. But when molecules do contain halogens, halogen bonds are often essential to understanding molecular
356:
of gas-phase halogen bond adducts, Legon and coworkers drew attention to the similarities between halogen-bonding and better-known hydrogen-bonding interactions.
352:
However, it was not until the mid-1990s, that the nature and applications of the halogen bond began to be intensively studied. Through systematic and extensive
469:
306:
direction that coincides with the axes of the orbitals of the lone pairs in the electron pair donor molecule. For this work, Hassel was awarded the 1969
207:
are usually better halogen-bond acceptors than neutral species: the more dissociated an ion pair is, the stronger the halogen bond formed with the anion.
400:, which attempts to shape crystal structures through close control of intermolecular interactions. Halogen bonds can stabilize copolymers or induce
2511:
68:
2041:
Pigge FC, Vangala VR, Kapadia PP, Swenson DC, Rath NP (October 2008). "Hexagonal crystalline inclusion complexes of 4-iodophenoxy trimesoate".
699:
Metrangolo P, Neukirch H, Pilati T, Resnati G (May 2005). "Halogen bonding based recognition processes: a world parallel to hydrogen bonding".
1942:
1575:
2006:
Nguyen HL, Horton PN, Hursthouse MB, Legon AC, Bruce DW (January 2004). "Halogen bonding: a new interaction for liquid crystal formation".
1860:
Janeta M, Szafert S (2017-10-01). "Synthesis, characterization and thermal properties of T8 type amido-POSS with p-halophenyl end-group".
282:
complex fifty years later, but the physical processes underlying the molecular interaction remained mysterious until the development of
1597:
Politzer P, Murray JS, Clark T (July 2010). "Halogen bonding: an electrostatically-driven highly directional noncovalent interaction".
2084:
Sun A, Lauher JW, Goroff NS (May 2006). "Preparation of poly(diiododiacetylene), an ordered conjugated polymer of carbon and iodine".
557:
231:
one. But halogen bonding is both much stronger and more sensitive to direction than hydrogen bonding. A typical hydrogen bond has
2629:
2556:
2237:
789:
737:
Gilday LC, Robinson SW, Barendt TA, Langton MJ, Mullaney BR, Beer PD (August 2015). "Halogen
Bonding in Supramolecular Chemistry".
463:
spontaneously, the halogen-bond induced organization is sufficiently strong that the cocrystals do spontaneously polymerize.
301:
patterns associated with a mixture of 1,4-dioxane and bromine. The patterns suggested that only 2.71 Ă
separated the dioxane
1899:, Pilati T, Terraneo G, Biella S (2009). "Anion coordination and anion-templated assembly under halogen bonding control".
1690:
164:
with the halogen atom's other, conventional bond, but the geometry of the electron-charge donor may be much more complex.
2551:
1421:
Mulliken RS (1950). "Structures of
Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents I.".
1833:
138:
as to polarize the associated Ï-bond. Consequently halogen-bond propensity follows the trend F < Cl < Br < I.
197:
186:
derivatives tend to donate halogen bonds approximately coplanar with the ring, and the two CâNâX angles are about 120°.
1463:
Mulliken RS (1952). "Molecular
Compounds and their Spectra. III. The Interaction of Electron Donors and Acceptors".
1279:
Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G (2008-08-04). "Halogen bonding in supramolecular chemistry".
2476:
2140:"Ultrahigh resolution drug design I: details of interactions in human aldose reductase-inhibitor complex at 0.66 A"
1966:"PerfluorocarbonâHydrocarbon Self-Assembling. 1D Infinite Chain Formation Driven by Nitrogen···Iodine Interactions"
313:
Dumas and coworkers first coined the term "halogen bond" in 1978, during their investigations into complexes of CCl
2300:
2491:
2660:
2327:
2288:
2278:
245:
The Ï-hole concept readily extends to pnictogen, chalcogen and aerogen bonds, corresponding to atoms of Groups
1239:"Reactions of pyridyl donors with halogens and interhalogens: an X-ray diffraction and FT-Raman investigation"
2283:
1834:"Scientists confirm decades-old theory of non-uniform distribution of electron density in aromatic molecules"
564:
through a bromine halogen bond, as shown in the figure. The molecules fail to bind to each other if similar
361:
63:
attraction. Mathematically, the interaction can be decomposed in two terms: one describing an electrostatic,
269:
Chains in the 1:1 adduct of 1,4-dioxane and bromine, the first crystallographic evidence of halogen bonding.
2230:
1775:
Mallada B, OndrĂĄÄek M, Lamanec M, Gallardo A, JimĂ©nez-MartĂn A, de la Torre B, et al. (August 2023).
148:; what is superficially a halogen bond may well turn out to be a full bond in an unexpectedly relevant
1238:
2655:
2546:
2536:
2526:
2501:
2471:
444:
2317:
1245:. III Euchem Conference on Nitrogen Ligands in Organometallic Chemistry and Homogeneous Catalysis.
511:
372:
307:
72:
1019:
Politzer P, Lane P, Concha MC, Ma Y, Murray JS (February 2007). "An overview of halogen bonding".
408:. Indeed, halogen bond-induced liquid crystalline phases are known in both alkoxystilbazoles and
2578:
2481:
2453:
2223:
1692:
456:
1691:
Institute of
Organic Chemistry and Biochemistry of the Czech Academy of Sciences (IOCB Prague).
878:
Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G (February 2016).
2138:
Howard EI, Sanishvili R, Cachau RE, Mitschler A, Chevrier B, Barth P, et al. (June 2004).
1237:
Aragoni MC, Arca M, Devillanova FA, Hursthouse MB, Huth SL, Isaia F, et al. (2005-04-15).
353:
443:
Conjugated polymers offer the tantalizing possibility of organic molecules with a manipulable
2622:
2583:
1353:
BauzĂĄ A, Frontera A (June 2015). "Aerogen
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64:
2617:
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Varadwaj, Pradeep R.; Varadwaj, Arpita; Marques, Helder M.; Yamashita, Koichi (2024-07-03).
2541:
2432:
2295:
2254:
2093:
1788:
1729:
1649:
1606:
939:
827:
448:
8:
2443:
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2273:
397:
149:
108:
84:
2607:
2097:
1809:
1792:
1776:
1733:
1653:
1610:
943:
831:
589:
2362:
2169:
2117:
2066:
1752:
1717:
1673:
1219:
1088:
1063:
1044:
1001:
904:
879:
565:
283:
1831:
930:
Hassel O (October 1970). "Structural aspects of interatomic charge-transfer bonding".
850:
815:
2593:
2382:
2342:
2332:
2161:
2109:
2058:
2023:
1985:
1946:
1877:
1873:
1814:
1757:
1677:
1665:
1622:
1579:
1493:
1370:
1335:
1296:
1258:
1254:
1223:
1211:
1160:
1143:
Eskandari K, Lesani M (March 2015). "Does fluorine participate in halogen bonding?".
1125:
1093:
1036:
993:
955:
909:
855:
793:
754:
716:
659:
Desiraju GR, Ho PS, Kloo L, Legon AC, Marquardt R, Metrangolo P, et al. (2013).
641:
432:
425:
396:
The strength and directionality of halogen bonds are a key tool in the discipline of
392:
Br···O halogen bonds observed in the 3D crystal structure of certain silsesquioxanes.
298:
224:
135:
2173:
2121:
2070:
1513:
1048:
1005:
572:
replaces the drug halogen, because the variant geometries inhibit the halogen bond.
475:
The catalyst-monomer cocrystal. Units repeat every 5.25 Ă
and are oriented at 51.3Ë.
2634:
2374:
2347:
2204:
2151:
2101:
2050:
2015:
1977:
1938:
1910:
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1804:
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1614:
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1201:
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835:
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633:
621:
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346:
228:
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44:
2612:
2486:
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951:
417:
334:
330:
1943:
10.1002/(SICI)1521-3773(20000515)39:10<1782::AID-ANIE1782>3.0.CO;2-5
1777:"Visualization of Ï-hole in molecules by means of Kelvin probe force microscopy"
1576:
10.1002/(sici)1521-3773(19990917)38:18<2686::aid-anie2686>3.0.co;2-6
895:
2521:
2322:
1800:
1742:
1693:"First observation of an inhomogeneous electron charge distribution on an atom"
820:
Proceedings of the National Academy of Sciences of the United States of America
542:
460:
413:
409:
220:
189:
142:
131:
120:
112:
88:
60:
1528:
Hassel O (1972). "Structural Aspects of Interatomic Charge-Transfer Bonding".
1032:
989:
2649:
2570:
2530:
2463:
2417:
2392:
2265:
2246:
1989:
1965:
1881:
1339:
1315:
1262:
677:
660:
645:
593:
388:
56:
52:
36:
2105:
1661:
840:
637:
533:. Interestingly, oxygen atoms typically do not attract halogens with their
119:
Halogen bonds occur when a halogen atom is electrostatically attracted to a
2195:
Bent, H. A. (1968). "Structural Chemistry of Donor-Acceptor Interactions".
2165:
2113:
2062:
2027:
1950:
1901:
1818:
1761:
1669:
1626:
1583:
1374:
1366:
1300:
1292:
1215:
1164:
1156:
1129:
1097:
1079:
1040:
997:
959:
913:
859:
797:
758:
720:
287:
161:
80:
48:
35:) occurs when there is evidence of a net attractive interaction between an
1196:
1179:
1064:"Halogen Bonding versus Hydrogen Bonding: A Molecular Orbital Perspective"
790:
10.1002/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T
2602:
2352:
1405:
553:
546:
538:
428:
239:
232:
76:
2208:
1476:
1455:
1434:
776:(June 2001). "Halogen bonding: a paradigm in supramolecular chemistry".
622:"Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit"
215:
A parallel relationship can easily be drawn between halogen bonding and
2156:
2139:
1206:
515:
294:
193:
145:
127:
2019:
1981:
1331:
750:
712:
371:
showed that halogen bonds also have a Ï-covalent character similar to
2337:
2312:
2054:
1914:
1618:
1316:"Fluorous Interpenetrated Layers in a Three-Component Crystal Matrix"
1121:
534:
401:
250:
246:
177:
124:
92:
20:
1964:
Amico V, Meille SV, Corradi E, Messina MT, Resnati G (August 1998).
1389:
103:
2411:
569:
523:
506:: a short Br−O halogen bond contributes to inhibitor potency.
431:
caused molecules to crystallize into a pattern that was nearly 40%
338:
183:
596:
from the category of halogen bonds. For a complete analysis, see
265:
2215:
1639:
1442:
Mulliken RS (1952). "Molecular Compounds and their Spectra. II".
342:
254:
200:
around the Lewis donor atom, can accept one or two halogen bonds.
40:
1313:
1236:
619:
16:
Net attractive interaction involving one of the halogen elements
2137:
1894:
698:
527:
519:
421:
416:
of halogen bonds can cause bulky molecules to crystallize into
405:
302:
1927:
1774:
1110:
375:. In August 2023 the "Ï-hole" was too experimentally observed
1314:
Liantonio R, Metrangolo P, Pilati T, Resnati G (2003-05-01).
877:
661:"Definition of the Halogen Bond (IUPAC Recommendations 2013)"
452:
173:
169:
1832:
Institute of Organic Chemistry and Biochemistry of the CAS.
1715:
1278:
975:
736:
2005:
2423:
2040:
447:, but current methods for production have an uncontrolled
1963:
597:
204:
123:. Necessarily, the atom must be covalently bonded in an
51:
region in another, or the same, molecular entity. Like a
814:
Auffinger P, Hays FA, Westhof E, Ho PS (November 2004).
514:. Computational studies suggest that known halogenated
141:
There is no clear distinction between halogen bonds and
210:
1716:
Kellett CW, Kennepohl P, Berlinguette CP (July 2020).
813:
297:
fruitfully applied the distinction to rationalize the
1542:
1177:
1018:
1596:
658:
451:. Sun, Lauher, and Goroff discovered that certain
1274:
1272:
1061:
771:
765:
694:
692:
690:
688:
227:relationship, between a halogen-like atom and an
2647:
2083:
1269:
1142:
2001:
1999:
1855:
1853:
873:
871:
869:
685:
71:dispersion. Halogen bonds find application in
2231:
2077:
1859:
1491:
1352:
732:
730:
420:; in one notable case, halogen bonds between
1178:Turunen L, Hansen JH, Erdélyi M (May 2021).
971:
969:
925:
923:
493:
438:
1996:
1850:
866:
598:§ Comparison to other bond-like forces
2238:
2224:
727:
590:hydrogen is sometimes considered a halogen
2155:
1808:
1751:
1741:
1512:
1205:
1195:
1087:
1062:Wolters LP, Bickelhaupt FM (April 2012).
966:
920:
903:
849:
839:
809:
807:
676:
2630:Polyhedral skeletal electron pair theory
2133:
2131:
2008:Journal of the American Chemical Society
1970:Journal of the American Chemical Society
1494:"The Structure of Bromine 1,4-Dioxanate"
1462:
1441:
1420:
497:
387:
264:
176:prefer halogen bonds collinear with the
155:
102:
1387:
816:"Halogen bonds in biological molecules"
67:charge-transfer and another describing
2648:
1530:In Nobel Lectures, Chemistry 1963-1970
1527:
1390:"Xxviii.âOn the Iodide of Iodammonium"
929:
804:
552:Halogen bonding can be significant in
383:
219:. Both interactions revolve around an
2219:
2128:
1561:
2194:
1180:"Halogen Bonding: An Odd Chemistry?"
290:affects the "outer sphere" instead.
211:Comparison to other bond-like forces
196:, and selenocarbonyl groups, with a
1862:Journal of Organometallic Chemistry
1599:Physical Chemistry Chemical Physics
1243:Journal of Organometallic Chemistry
13:
2245:
2187:
455:ensure a linear polymerization of
14:
2672:
1718:"Ï covalency in the halogen bond"
652:
556:as well. For example, inhibitor
412:(pictured). Alternatively, the
2422:
2416:
2410:
1874:10.1016/j.jorganchem.2017.05.044
1255:10.1016/j.jorganchem.2004.11.001
480:
468:
107:Halogen bond in complex between
2034:
1957:
1921:
1888:
1825:
1768:
1709:
1684:
1633:
1590:
1555:
1536:
1521:
1514:10.3891/acta.chem.scand.08-0873
1485:
1412:
1381:
1346:
1307:
1230:
1171:
1136:
1104:
1055:
1012:
582:
378:
613:
168:Multi-electron donors such as
1:
1021:Journal of Molecular Modeling
978:Journal of Molecular Modeling
701:Accounts of Chemical Research
607:
362:Kelvin probe force microscopy
98:
55:, the result is not a formal
1937:(10). Wiley-VCH: 1782â1786.
1492:Hassel O, Hvoslef J (1954).
952:10.1126/science.170.3957.497
7:
1320:Crystal Growth & Design
896:10.1021/acs.chemrev.5b00484
626:Crystal Growth & Design
10:
2677:
2328:Metalâligand multiple bond
1801:10.1038/s41467-023-40593-3
1743:10.1038/s41467-020-17122-7
260:
242:range from 10â200 kJ/mol.
2592:
2569:
2500:
2462:
2442:
2431:
2408:
2391:
2373:
2264:
2253:
1033:10.1007/s00894-006-0154-7
990:10.1007/s00894-006-0130-2
502:IDD 594 binding to human
494:Biological macromolecules
445:electronic band structure
439:Controlled polymerization
160:A halogen bond is almost
39:region associated with a
678:10.1351/pac-rec-12-05-10
575:
568:replaces the enzyme, or
518:form halogen bonds with
373:metal coordination bonds
308:Nobel Prize in Chemistry
198:trigonal planar geometry
73:supramolecular chemistry
2106:10.1126/science.1124621
2043:Chemical Communications
1662:10.1126/science.abk1479
841:10.1073/pnas.0407607101
638:10.1021/acs.cgd.4c00228
457:poly(diiododiacetylene)
404:in otherwise isotropic
121:partial negative charge
1367:10.1002/anie.201502571
1293:10.1002/anie.200800128
1157:10.1002/chem.201405054
1080:10.1002/open.201100015
592:, convention excludes
507:
393:
354:microwave spectroscopy
270:
116:
59:, but rather a strong
2661:Intermolecular forces
1781:Nature Communications
1722:Nature Communications
1197:10.1002/tcr.202100060
501:
391:
349:in organic solvents.
268:
156:Donor characteristics
134:or the halogen is so
106:
2318:Coordinate (dipolar)
1406:10.1039/js8631600239
2492:CâH···O interaction
2274:Electron deficiency
2209:10.1021/cr60255a003
2098:2006Sci...312.1030S
2092:(5776): 1030â1034.
1793:2023NatCo..14.4954M
1734:2020NatCo..11.3310K
1654:2021Sci...374..863M
1611:2010PCCP...12.7748P
1477:10.1021/j150499a001
1456:10.1021/ja01123a067
1435:10.1021/ja01157a151
1114:Dalton Transactions
944:1970Sci...170..497H
832:2004PNAS..10116789A
826:(48): 16789â16794.
398:crystal engineering
384:Crystal engineering
233:energy of formation
150:resonance structure
109:iodine monochloride
85:crystal engineering
2477:Resonance-assisted
2157:10.1002/prot.20015
1388:Guthrie F (1863).
880:"The Halogen Bond"
566:aldehyde reductase
508:
414:steric sensitivity
394:
284:Robert S. Mulliken
271:
180:and donor nucleus.
117:
2643:
2642:
2594:Electron counting
2565:
2564:
2454:London dispersion
2406:
2405:
2383:Metal aromaticity
2193:An early review:
2049:(39): 4726â4728.
2020:10.1021/ja036994l
1982:10.1021/ja9810686
1976:(32): 8261â8262.
1931:Angewandte Chemie
1648:(6569): 863â867.
1605:(28): 7748â7757.
1570:(18): 2686â2714.
1564:Angewandte Chemie
1361:(25): 7340â7343.
1355:Angewandte Chemie
1332:10.1021/cg0340244
1287:(33): 6114â6127.
1281:Angewandte Chemie
1151:(12): 4739â4746.
1116:(13): 2252â2258.
938:(3957): 497â502.
784:(12): 2511â2519.
751:10.1021/cr500674c
745:(15): 7118â7195.
713:10.1021/ar0400995
632:(13): 5494â5525.
541:electrons in the
537:, but rather the
418:porous structures
367:In 2020, Kellett
299:X-ray diffraction
225:electron acceptor
2668:
2656:Chemical bonding
2635:Jemmis mno rules
2487:Dihydrogen bonds
2440:
2439:
2426:
2420:
2414:
2348:Hyperconjugation
2262:
2261:
2240:
2233:
2226:
2217:
2216:
2212:
2182:
2181:
2159:
2135:
2126:
2125:
2081:
2075:
2074:
2055:10.1039/b809592b
2038:
2032:
2031:
2003:
1994:
1993:
1961:
1955:
1954:
1925:
1919:
1918:
1915:10.1039/B821300C
1909:(7): 1187â1196.
1892:
1886:
1885:
1857:
1848:
1847:
1845:
1844:
1829:
1823:
1822:
1812:
1772:
1766:
1765:
1755:
1745:
1713:
1707:
1706:
1704:
1703:
1688:
1682:
1681:
1637:
1631:
1630:
1619:10.1039/c004189k
1594:
1588:
1587:
1559:
1553:
1552:
1545:J. Chem. Res.(S)
1540:
1534:
1533:
1525:
1519:
1518:
1516:
1501:Acta Chem. Scand
1498:
1489:
1483:
1480:
1459:
1444:J. Am. Chem. Soc
1438:
1423:J. Am. Chem. Soc
1416:
1410:
1409:
1385:
1379:
1378:
1350:
1344:
1343:
1311:
1305:
1304:
1276:
1267:
1266:
1249:(8): 1923â1934.
1234:
1228:
1227:
1209:
1199:
1190:(5): 1252â1257.
1175:
1169:
1168:
1140:
1134:
1133:
1122:10.1039/B503883A
1108:
1102:
1101:
1091:
1059:
1053:
1052:
1016:
1010:
1009:
973:
964:
963:
927:
918:
917:
907:
890:(4): 2478â2601.
884:Chemical Reviews
875:
864:
863:
853:
843:
811:
802:
801:
769:
763:
762:
739:Chemical Reviews
734:
725:
724:
696:
683:
682:
680:
671:(8): 1711â1713.
656:
650:
649:
617:
601:
586:
562:aldose reductase
504:aldose reductase
484:
472:
347:di-n-butyl ether
257:(respectively).
238:; known halogen
237:
217:hydrogen bonding
132:polarizes poorly
45:molecular entity
2676:
2675:
2671:
2670:
2669:
2667:
2666:
2665:
2646:
2645:
2644:
2639:
2588:
2561:
2504:
2496:
2458:
2445:
2435:
2427:
2421:
2415:
2402:
2387:
2369:
2257:
2249:
2244:
2190:
2188:Further reading
2185:
2136:
2129:
2082:
2078:
2039:
2035:
2004:
1997:
1962:
1958:
1926:
1922:
1893:
1889:
1858:
1851:
1842:
1840:
1830:
1826:
1773:
1769:
1714:
1710:
1701:
1699:
1689:
1685:
1638:
1634:
1595:
1591:
1560:
1556:
1541:
1537:
1526:
1522:
1496:
1490:
1486:
1417:
1413:
1386:
1382:
1351:
1347:
1312:
1308:
1277:
1270:
1235:
1231:
1184:Chemical Record
1176:
1172:
1141:
1137:
1109:
1105:
1060:
1056:
1017:
1013:
974:
967:
928:
921:
876:
867:
812:
805:
770:
766:
735:
728:
697:
686:
665:Pure Appl. Chem
657:
653:
618:
614:
610:
605:
604:
587:
583:
578:
560:binds to human
496:
489:
485:
476:
473:
441:
410:silsesquioxanes
386:
381:
335:tetrahydropyran
331:tetrahydrofuran
328:
324:
320:
316:
293:Then, in 1954,
281:
277:
263:
235:
213:
158:
136:electronegative
101:
89:liquid crystals
17:
12:
11:
5:
2674:
2664:
2663:
2658:
2641:
2640:
2638:
2637:
2632:
2627:
2626:
2625:
2620:
2615:
2610:
2599:
2597:
2590:
2589:
2587:
2586:
2581:
2575:
2573:
2567:
2566:
2563:
2562:
2560:
2559:
2554:
2549:
2544:
2539:
2534:
2524:
2519:
2514:
2508:
2506:
2498:
2497:
2495:
2494:
2489:
2484:
2479:
2474:
2468:
2466:
2460:
2459:
2457:
2456:
2450:
2448:
2437:
2433:Intermolecular
2429:
2428:
2409:
2407:
2404:
2403:
2401:
2400:
2397:
2395:
2389:
2388:
2386:
2385:
2379:
2377:
2371:
2370:
2368:
2367:
2366:
2365:
2360:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2304:
2303:
2293:
2292:
2291:
2286:
2281:
2270:
2268:
2259:
2255:Intramolecular
2251:
2250:
2247:Chemical bonds
2243:
2242:
2235:
2228:
2220:
2214:
2213:
2203:(5): 587â648.
2189:
2186:
2184:
2183:
2150:(4): 792â804.
2127:
2076:
2033:
1995:
1956:
1920:
1895:Metrangolo P,
1887:
1849:
1824:
1767:
1708:
1683:
1632:
1589:
1554:
1535:
1520:
1484:
1482:
1481:
1471:(7): 801â822.
1460:
1450:(3): 811â824.
1439:
1411:
1380:
1345:
1326:(3): 355â361.
1306:
1268:
1229:
1170:
1135:
1103:
1054:
1027:(2): 305â311.
1011:
984:(2): 291â296.
965:
919:
865:
803:
772:Metrangolo P,
764:
726:
707:(5): 386â395.
684:
651:
611:
609:
606:
603:
602:
594:hydrogen bonds
580:
579:
577:
574:
495:
492:
491:
490:
486:
479:
477:
474:
467:
440:
437:
385:
382:
380:
377:
326:
322:
318:
314:
279:
275:
262:
259:
236:20 kJ/mol
229:electron-dense
221:electron donor
212:
209:
202:
201:
187:
181:
157:
154:
143:expanded octet
113:trimethylamine
100:
97:
91:; and organic
69:electron-cloud
65:orbital-mixing
15:
9:
6:
4:
3:
2:
2673:
2662:
2659:
2657:
2654:
2653:
2651:
2636:
2633:
2631:
2628:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2608:HĂŒckel's rule
2606:
2605:
2604:
2601:
2600:
2598:
2595:
2591:
2585:
2582:
2580:
2577:
2576:
2574:
2572:
2571:Bond cleavage
2568:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2537:Intercalation
2535:
2532:
2528:
2527:Metallophilic
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2509:
2507:
2503:
2499:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2469:
2467:
2465:
2461:
2455:
2452:
2451:
2449:
2447:
2444:Van der Waals
2441:
2438:
2434:
2430:
2425:
2419:
2413:
2399:
2398:
2396:
2394:
2390:
2384:
2381:
2380:
2378:
2376:
2372:
2364:
2361:
2359:
2356:
2355:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2302:
2299:
2298:
2297:
2294:
2290:
2287:
2285:
2282:
2280:
2277:
2276:
2275:
2272:
2271:
2269:
2267:
2263:
2260:
2256:
2252:
2248:
2241:
2236:
2234:
2229:
2227:
2222:
2221:
2218:
2210:
2206:
2202:
2198:
2192:
2191:
2180:
2175:
2171:
2167:
2163:
2158:
2153:
2149:
2145:
2141:
2134:
2132:
2123:
2119:
2115:
2111:
2107:
2103:
2099:
2095:
2091:
2087:
2080:
2072:
2068:
2064:
2060:
2056:
2052:
2048:
2044:
2037:
2029:
2025:
2021:
2017:
2013:
2009:
2002:
2000:
1991:
1987:
1983:
1979:
1975:
1971:
1967:
1960:
1952:
1948:
1944:
1940:
1936:
1932:
1924:
1916:
1912:
1908:
1904:
1903:
1898:
1891:
1883:
1879:
1875:
1871:
1867:
1863:
1856:
1854:
1839:
1835:
1828:
1820:
1816:
1811:
1806:
1802:
1798:
1794:
1790:
1786:
1782:
1778:
1771:
1763:
1759:
1754:
1749:
1744:
1739:
1735:
1731:
1727:
1723:
1719:
1712:
1698:
1694:
1687:
1679:
1675:
1671:
1667:
1663:
1659:
1655:
1651:
1647:
1643:
1636:
1628:
1624:
1620:
1616:
1612:
1608:
1604:
1600:
1593:
1585:
1581:
1577:
1573:
1569:
1565:
1558:
1550:
1546:
1539:
1531:
1524:
1515:
1510:
1506:
1502:
1495:
1488:
1478:
1474:
1470:
1466:
1465:J. Phys. Chem
1461:
1457:
1453:
1449:
1445:
1440:
1436:
1432:
1428:
1424:
1419:
1418:
1415:
1407:
1403:
1399:
1395:
1391:
1384:
1376:
1372:
1368:
1364:
1360:
1356:
1349:
1341:
1337:
1333:
1329:
1325:
1321:
1317:
1310:
1302:
1298:
1294:
1290:
1286:
1282:
1275:
1273:
1264:
1260:
1256:
1252:
1248:
1244:
1240:
1233:
1225:
1221:
1217:
1213:
1208:
1203:
1198:
1193:
1189:
1185:
1181:
1174:
1166:
1162:
1158:
1154:
1150:
1146:
1139:
1131:
1127:
1123:
1119:
1115:
1107:
1099:
1095:
1090:
1085:
1081:
1077:
1074:(2): 96â105.
1073:
1069:
1068:ChemistryOpen
1065:
1058:
1050:
1046:
1042:
1038:
1034:
1030:
1026:
1022:
1015:
1007:
1003:
999:
995:
991:
987:
983:
979:
972:
970:
961:
957:
953:
949:
945:
941:
937:
933:
926:
924:
915:
911:
906:
901:
897:
893:
889:
885:
881:
874:
872:
870:
861:
857:
852:
847:
842:
837:
833:
829:
825:
821:
817:
810:
808:
799:
795:
791:
787:
783:
779:
775:
768:
760:
756:
752:
748:
744:
740:
733:
731:
722:
718:
714:
710:
706:
702:
695:
693:
691:
689:
679:
674:
670:
666:
662:
655:
647:
643:
639:
635:
631:
627:
623:
616:
612:
599:
595:
591:
585:
581:
573:
571:
567:
563:
559:
555:
550:
548:
544:
540:
536:
532:
529:
525:
521:
517:
513:
505:
500:
483:
478:
471:
466:
465:
464:
462:
458:
454:
450:
446:
436:
434:
430:
427:
423:
419:
415:
411:
407:
403:
399:
390:
376:
374:
370:
365:
363:
357:
355:
350:
348:
344:
340:
336:
332:
311:
309:
304:
300:
296:
291:
289:
288:Lewis adducts
285:
267:
258:
256:
252:
248:
243:
241:
240:bond energies
234:
230:
226:
222:
218:
208:
206:
199:
195:
194:thiocarbonyl-
191:
188:
185:
182:
179:
175:
171:
167:
166:
165:
163:
153:
151:
147:
146:partial bonds
144:
139:
137:
133:
129:
126:
122:
114:
110:
105:
96:
94:
90:
86:
82:
78:
74:
70:
66:
62:
61:electrostatic
58:
57:chemical bond
54:
53:hydrogen bond
50:
46:
42:
38:
37:electrophilic
34:
30:
26:
22:
2613:Baird's rule
2516:
2333:Charge-shift
2296:Hypervalence
2200:
2196:
2177:
2147:
2143:
2089:
2085:
2079:
2046:
2042:
2036:
2014:(1): 16â17.
2011:
2007:
1973:
1969:
1959:
1934:
1930:
1923:
1906:
1902:CrystEngComm
1900:
1890:
1865:
1861:
1841:. Retrieved
1837:
1827:
1784:
1780:
1770:
1725:
1721:
1711:
1700:. Retrieved
1696:
1686:
1645:
1641:
1635:
1602:
1598:
1592:
1567:
1563:
1557:
1548:
1544:
1538:
1529:
1523:
1504:
1500:
1487:
1468:
1464:
1447:
1443:
1426:
1422:
1414:
1397:
1394:J. Chem. Soc
1393:
1383:
1358:
1354:
1348:
1323:
1319:
1309:
1284:
1280:
1246:
1242:
1232:
1187:
1183:
1173:
1148:
1144:
1138:
1113:
1106:
1071:
1067:
1057:
1024:
1020:
1014:
981:
977:
935:
931:
887:
883:
823:
819:
781:
777:
767:
742:
738:
704:
700:
668:
664:
654:
629:
625:
615:
584:
551:
530:
512:conformation
509:
442:
402:mesomorphism
395:
379:Applications
368:
366:
358:
351:
312:
303:oxygen atoms
292:
272:
244:
214:
203:
159:
140:
118:
81:biochemistry
49:nucleophilic
32:
28:
25:halogen bond
24:
18:
2603:Aromaticity
2579:Heterolysis
2557:Salt bridge
2502:Noncovalent
2472:Low-barrier
2353:Aromaticity
2343:Conjugation
2323:Pi backbond
1868:: 173â183.
1787:(1): 4954.
1728:(1): 3310.
1400:: 239â244.
1207:10037/22989
554:drug design
547:amide group
516:nucleobases
77:drug design
2650:Categories
2531:aurophilic
2512:Mechanical
1843:2023-09-07
1702:2023-09-07
1532:: 314â329.
1429:(1): 600.
608:References
535:lone pairs
461:polymerize
429:Ï-orbitals
325:, and SiBr
295:Odd Hassel
99:Definition
43:atom in a
2623:spherical
2584:Homolysis
2547:Cationâpi
2522:Chalcogen
2482:Symmetric
2338:Hapticity
2197:Chem. Rev
1990:0002-7863
1897:Resnati G
1882:0022-328X
1678:244039573
1340:1528-7483
1263:0022-328X
1224:233483539
1145:Chemistry
778:Chemistry
774:Resnati G
646:1528-7483
588:Although
178:lone pair
162:collinear
125:antipodal
93:catalysis
21:chemistry
2552:Anionâpi
2542:Stacking
2464:Hydrogen
2375:Metallic
2266:Covalent
2258:(strong)
2174:38388856
2166:15146478
2144:Proteins
2122:36045120
2114:16709780
2071:40424594
2063:18830473
2028:14709037
1951:10934360
1838:phys.org
1819:37587123
1810:10432393
1762:32620765
1697:phys.org
1670:34762455
1627:20571692
1584:10508357
1551:: 54â57.
1375:25950423
1301:18651626
1216:33939244
1165:25652256
1130:15962045
1098:24551497
1049:39255577
1041:17013631
1006:93970509
998:16927107
960:17799698
914:26812185
860:15557000
798:11465442
759:26165273
721:15895976
570:chlorine
543:carbonyl
531:in vitro
524:nitrogen
449:topology
426:aromatic
339:pyridine
190:Carbonyl
184:Pyridine
2517:Halogen
2363:bicyclo
2308:Agostic
2094:Bibcode
2086:Science
1789:Bibcode
1753:7335087
1730:Bibcode
1650:Bibcode
1642:Science
1607:Bibcode
1507:: 873.
1089:3922460
940:Bibcode
932:Science
905:4768247
828:Bibcode
558:IDD 594
406:liquids
343:anisole
261:History
41:halogen
2618:Möbius
2446:forces
2436:(weak)
2172:
2164:
2120:
2112:
2069:
2061:
2026:
1988:
1949:
1880:
1817:
1807:
1760:
1750:
1676:
1668:
1625:
1582:
1373:
1338:
1299:
1261:
1222:
1214:
1163:
1128:
1096:
1086:
1047:
1039:
1004:
996:
958:
912:
902:
858:
851:529416
848:
796:
757:
719:
644:
528:sulfur
520:oxygen
488:line).
453:amides
422:iodine
369:et al.
345:, and
321:, SiCl
205:Anions
174:amines
170:ethers
128:Ï-bond
47:and a
2596:rules
2505:other
2393:Ionic
2301:3câ4e
2289:8câ2e
2284:4câ2e
2279:3câ2e
2170:S2CID
2118:S2CID
2067:S2CID
1674:S2CID
1497:(PDF)
1220:S2CID
1045:S2CID
1002:S2CID
576:Notes
526:, or
329:with
317:, CBr
278:···NH
2358:homo
2313:Bent
2162:PMID
2110:PMID
2059:PMID
2024:PMID
1986:ISSN
1947:PMID
1878:ISSN
1815:PMID
1758:PMID
1666:PMID
1623:PMID
1580:PMID
1371:PMID
1336:ISSN
1297:PMID
1259:ISSN
1212:PMID
1161:PMID
1126:PMID
1094:PMID
1037:PMID
994:PMID
956:PMID
910:PMID
856:PMID
794:PMID
755:PMID
717:PMID
642:ISSN
433:void
424:and
253:and
172:and
111:and
87:and
79:and
23:, a
2205:doi
2152:doi
2102:doi
2090:312
2051:doi
2016:doi
2012:126
1978:doi
1974:120
1939:doi
1911:doi
1870:doi
1866:847
1805:PMC
1797:doi
1748:PMC
1738:doi
1658:doi
1646:374
1615:doi
1572:doi
1509:doi
1473:doi
1452:doi
1431:doi
1402:doi
1363:doi
1328:doi
1289:doi
1251:doi
1247:690
1202:hdl
1192:doi
1153:doi
1118:doi
1084:PMC
1076:doi
1029:doi
986:doi
948:doi
936:170
900:PMC
892:doi
888:116
846:PMC
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