55:
1400:
1449:. In the same way, bases could be classified. For example, bases donating a lone pair from an oxygen atom are harder than bases donating through a nitrogen atom. Although the classification was never quantified it proved to be very useful in predicting the strength of adduct formation, using the key concepts that hard acidâhard base and soft acidâsoft base interactions are stronger than hard acidâsoft base or soft acidâhard base interactions. Later investigation of the thermodynamics of the interaction suggested that hardâhard interactions are
624:
1527:
31:
1517:
The W term represents a constant energy contribution for acidâbase reaction such as the cleavage of a dimeric acid or base. The equation predicts reversal of acids and base strengths. The graphical presentations of the equation show that there is no single order of Lewis base strengths or Lewis acid
590:
Although there have been attempts to use computational and experimental energetic criteria to distinguish dative bonding from non-dative covalent bonds, for the most part, the distinction merely makes note of the source of the electron pair, and dative bonds, once formed, behave simply as other
909:(H)â is one of the strongest but is also one of the most complicated Lewis acids. It is convention to ignore the fact that a proton is heavily solvated (bound to solvent). With this simplification in mind, acid-base reactions can be viewed as the formation of adducts:
1553:
was published in the same year. The two theories are distinct but complementary. A Lewis base is also a BrønstedâLowry base, but a Lewis acid does not need to be a BrønstedâLowry acid. The classification into hard and soft acids and bases
607:), the use of the dative bond arrow is just a notational convenience for avoiding the drawing of formal charges. In general, however, the donorâacceptor bond is viewed as simply somewhere along a continuum between idealized
54:
1617:
A Lewis base is often a BrønstedâLowry base as it can donate a pair of electrons to H; the proton is a Lewis acid as it can accept a pair of electrons. The conjugate base of a BrønstedâLowry acid is also a Lewis base as
425:) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific
515:. Some sources indicate the Lewis base with a pair of dots (the explicit electrons being donated), which allows consistent representation of the transition from the base itself to the complex with the acid:
1476:
is a quantitative model that describes and predicts the strength of Lewis acid base interactions, âÎH. The model assigned E and C parameters to many Lewis acids and bases. Each acid is characterized by an
1771:
From p. 142: "We are inclined to think of substances as possessing acid or basic properties, without having a particular solvent in mind. It seems to me that with complete generality we may say that
1420:
Lewis acids and bases are commonly classified according to their hardness or softness. In this context hard implies small and nonpolarizable and soft indicates larger atoms that are more polarizable.
634:
Lewis acids are diverse and the term is used loosely. Simplest are those that react directly with the Lewis base, such as boron trihalides and the pentahalides of phosphorus, arsenic, and antimony.
496:
In many cases, the interaction between the Lewis base and Lewis acid in a complex is indicated by an arrow indicating the Lewis base donating electrons toward the Lewis acid using the notation of a
649:
can be considered to be the Lewis acid in methylation reactions. However, the methyl cation never occurs as a free species in the condensed phase, and methylation reactions by reagents like CH
834:
are treated as trigonal planar Lewis acids but exist as aggregates and polymers that must be degraded by the Lewis base. A simpler case is the formation of adducts of borane. Monomeric BH
1779:
in completing the stable group of one of its own atoms. In other words, the basic substance furnishes a pair of electrons for a chemical bond, the acid substance accepts such a pair."
1645:. This example demonstrates that steric factors, in addition to electron configuration factors, play a role in determining the strength of the interaction between the bulky di-
423:
1493:. The E and C parameters refer, respectively, to the electrostatic and covalent contributions to the strength of the bonds that the acid and base will form. The equation is
2266:
Brown, Herbert C.; Kanner, Bernard (1966). "Preparation and
Reactions of 2,6-Di-t-butylpyridine and Related Hindered Bases. A Case of Steric Hindrance toward the Proton".
2043:
1948:
1720:
657:
2 reaction). Textbooks disagree on this point: some asserting that alkyl halides are electrophiles but not Lewis acids, while others describe alkyl halides (e.g. CH
1902:
1822:
Lepetit, Christine; Maraval, ValĂŠrie; Canac, Yves; Chauvin, Remi (2016). "On the Nature of the Dative Bond: Coordination to Metals and Beyond. The Carbon Case".
1465:
Many methods have been devised to evaluate and predict Lewis acidity. Many are based on spectroscopic signatures such as shifts NMR signals or IR bands e.g. the
1673:
1622:
from the acid leaves those electrons which were used for the AâH bond as a lone pair on the conjugate base. However, a Lewis base can be very difficult to
1594:
ion that is formed. Nevertheless, Lewis suggested that an electron-pair donor be classified as a base and an electron-pair acceptor be classified as acid.
1550:
247:
188:
812:
Most compounds considered to be Lewis acids require an activation step prior to formation of the adduct with the Lewis base. Complex compounds such as
308:
2183:
Cramer, Roger E.; Bopp, Thomas T. (1977). "Great e and C plot. Graphical display of the enthalpies of adduct formation for Lewis acids and bases".
653:
I take place through the simultaneous formation of a bond from the nucleophile to the carbon and cleavage of the bond between carbon and iodine (S
2217:
Miessler, L. M., Tar, D. A., (1991) p. 166 â Table of discoveries attributes the date of publication/release for the Lewis theory as 1923.
2099:
2077:
1878:
1547:
An acid substance is one which can employ an electron lone pair from another molecule in completing the stable group of one of its own atoms.
1574:
are held together in a chemical bond by sharing a pair of electrons. When each atom contributed one electron to the bond, it was called a
591:
covalent bonds do, though they typically have considerable polar character. Moreover, in some cases (e.g., sulfoxides and amine oxides as
773:
The variability of the colors of iodine solutions reflects the variable abilities of the solvent to form adducts with the Lewis acid I
552:
2328:
2309:
2017:
1925:
1856:
1764:
2347:
1978:
Rowsell, Bryan D.; Gillespie, Ronald J.; Heard, George L. (1999). "Ligand Close-Packing and the Lewis
Acidity of BF3 and BCl3".
472:
are sometimes interchangeable with Lewis base and Lewis acid, respectively. These terms, especially their abstract noun forms
1798:
945:
884:
Many metal complexes serve as Lewis acids, but usually only after dissociating a more weakly bound Lewis base, often water.
1773:
a basic substance is one which has a lone pair of electrons which may be used to complete the stable group of another atom
813:
301:
1582:. The distinction is not very clear-cut. For example, in the formation of an ammonium ion from ammonia and hydrogen the
2072:
Christian
Laurence and Jean-François Gal "Lewis Basicity and Affinity Scales : Data and Measurement" Wiley, 2009.
1688:
627:
Major structural changes accompany binding of the Lewis base to the coordinatively unsaturated, planar Lewis acid BF
2357:
1759:. American chemical society. Monograph series. New York, New York, U.S.A.: Chemical Catalog Company. p. 142.
79:
2012:
Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the
Elements (2nd Edn.), Oxford:Butterworth-Heinemann.
124:
568:
294:
144:
129:
665:
states that Lewis acids and Lewis bases react to form Lewis adducts, and defines electrophile as Lewis acids.
149:
1698:
1668:
1399:
74:
2117:"Lewis acid adducts of ι,β-unsaturated carbonyl and nitrile compounds. A nuclear magnetic resonance study"
1466:
1683:
1377:
1369:
1359:
277:
159:
119:
109:
623:
349:, then, is any species that has a filled orbital containing an electron pair which is not involved in
2228:
2192:
2157:
1381:
375:
154:
1164:
1339:
330:
1597:
A more modern definition of a Lewis acid is an atomic or molecular species with a localized empty
2248:
2035:
1896:
1587:
1364:
Nearly all electron pair donors that form compounds by binding transition elements can be viewed
1326:
1257:
828:
781:
838:
does not exist appreciably, so the adducts of borane are generated by degradation of diborane:
2324:
2305:
2297:
2095:
2073:
2013:
1995:
1931:
1921:
1884:
1874:
1852:
1804:
1794:
1760:
1754:
1678:
1602:
1558:) followed in 1963. The strength of Lewis acid-base interactions, as measured by the standard
1244:
1167:
584:
426:
164:
1518:
strengths. and that single property scales are limited to a smaller range of acids or bases.
2275:
2240:
2200:
2165:
2128:
2057:
1987:
1962:
1831:
1734:
1663:
1542:
1538:
608:
454:
338:
326:
267:
237:
99:
89:
1066:
The most common Lewis bases are anions. The strength of Lewis basicity correlates with the
1627:
1579:
1578:. When both electrons come from one of the atoms, it was called a dative covalent bond or
662:
369:
139:
104:
64:
2196:
2161:
1641:-butylpyridine reacts to form the hydrochloride salt with HCl but does not react with BF
1562:
of formation of an adduct can be predicted by the DragoâWayland two-parameter equation.
1368:. Thus, a large application of Lewis bases is to modify the activity and selectivity of
1092:
Examples of Lewis bases based on the general definition of electron pair donor include:
2352:
1598:
1385:
1085:
485:
481:
1637:
In another comparison of Lewis and BrønstedâLowry acidity by Brown and Kanner, 2,6-di-
1526:
30:
2341:
1619:
1575:
1201:
1081:
965:
674:
612:
350:
334:
84:
2252:
2053:
1958:
1851:
March, J. âAdvanced
Organic Chemistryâ 4th Ed. J. Wiley and Sons, 1992: New York.
1730:
780:
Some Lewis acids bind with two Lewis bases, a famous example being the formation of
1373:
1313:
1283:
1231:
1188:
673:
Some of the most studied examples of such Lewis acids are the boron trihalides and
468:
257:
208:
203:
198:
114:
1430:
typical hard bases: ammonia and amines, water, carboxylates, fluoride and chloride
1150:
The strength of Lewis bases have been evaluated for various Lewis acids, such as I
2048:
1953:
1725:
1623:
1555:
1415:
497:
462:
354:
262:
213:
94:
484:
aspect of reactivity, while the Lewis basicity and Lewis acidity emphasize the
1888:
1835:
1530:
1389:
743:
228:
2052:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1957:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
1729:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
2061:
1966:
1935:
1808:
1738:
1693:
1473:
1442:
1114:
1036:
747:
365:
282:
272:
223:
218:
169:
1999:
1777:
an acid substance is one which can employ a lone pair from another molecule
567:. In a slightly different usage, the center dot is also used to represent
17:
1591:
1559:
1450:
1433:
typical soft bases: organophosphines, thioethers, carbon monoxide, iodide
1218:
1100:
1009:
2279:
2244:
587:, irrespective of whether the water forms a dative bond with the metal.
1630:
is a very weak BrønstedâLowry base but it forms a strong adduct with BF
1583:
1454:
1424:
typical hard acids: H, alkali/alkaline earth metal cations, boranes, Zn
1300:
1142:
1124:
1096:
358:
2204:
2169:
1991:
2039:
1365:
1138:
1134:
1060:
1055:
compounds of O, S, Se and Te in oxidation state â2, including water,
906:
701:
342:
2133:
2116:
1533:
depicting the formation of a dative covalent bond between two atoms
540:
A center dot may also be used to represent a Lewis adduct, such as
1793:. Dougherty, Dennis A., 1952-. Sausalito, CA: University Science.
1525:
1438:
1056:
1005:
1001:
622:
29:
1012:
and its derivatives. Some of the main classes of Lewis bases are
1000:(HOMO) is highly localized. Typical Lewis bases are conventional
1658:
1606:
1571:
1030:
997:
178:
69:
700:
In this adduct, all four fluoride centres (or more accurately,
1270:
1716:
1714:
1605:
orbital of low energy. This lowest-energy molecular orbital (
2148:
Vogel, Glenn C.; Drago, Russell S. (1996). "The ECW Model".
2090:
Jacobsen, E.N.; Pfaltz, Andreas; Yamamato, H., eds. (1999).
1398:
134:
1388:. The industrial synthesis of the anti-hypertension drug
1873:. Neil Eric Schore (8th ed.). New York. p. 73.
996:
A Lewis base is an atomic or molecular species where the
408:
395:
357:
with a Lewis acid to form a Lewis adduct. For example,
944:
A typical example of a Lewis acid in action is in the
378:
1033:. Related to these are pyridine and its derivatives.
441:
will form a dative bond with the empty orbital of Me
2094:. Berlin; New York: Springer. pp. 1443â1445.
1626:, yet still react with a Lewis acid. For example,
1485:. Each base is likewise characterized by its own E
417:
1920:(5th ed.). Boston: McGraw-Hill. p. 46.
453:. The terminology refers to the contributions of
2115:Childs, R.F; Mulholland, D.L; Nixon, A. (1982).
1756:Valence and the Structure of Atoms and Molecules
948:reaction. The key step is the acceptance by AlCl
2321:Lewis acid reagents : a practical approach
2302:The Lewis acid-base concepts : an overview
1871:Organic chemistry : structure and function
1590:; the identity of the electrons is lost in the
329:) is a chemical species that contains an empty
1748:
1746:
1105:other lone-pair-containing species, such as H
739:are Lewis base adducts of boron trifluoride.
302:
8:
1586:molecule donates a pair of electrons to the
964:and creating the strongly acidic, that is,
364:is a Lewis base, because it can donate its
1901:: CS1 maint: location missing publisher (
309:
295:
44:
2132:
2030:
2028:
2026:
1008:amines. Other common Lewis bases include
407:
402:
394:
389:
381:
379:
377:
325:(named for the American physical chemist
2268:Journal of the American Chemical Society
2233:Journal of the American Chemical Society
1427:typical soft acids: Ag, Mo(0), Ni(0), Pt
1384:, which is useful for the production of
868:
602:
594:
574:
562:
558:
547:
543:
533:
529:
525:
521:
511:
503:
1847:
1845:
1710:
1609:) can accommodate a pair of electrons.
236:
177:
47:
1894:
1080:'s give good Lewis bases. As usual, a
2323:. New York: Oxford University Press.
1613:Comparison with BrønstedâLowry theory
1570:Lewis had suggested in 1916 that two
1166:Heats of binding of various bases to
952:of a chloride ion lone-pair, forming
7:
1073:of the parent acid: acids with high
2092:Comprehensive Asymmetric Catalysis
2049:Compendium of Chemical Terminology
2034:Traditionally, but not precisely,
1954:Compendium of Chemical Terminology
1726:Compendium of Chemical Terminology
1183:Enthalpy of complexation (kJ/mol)
998:highest occupied molecular orbital
553:boron trifluoride diethyl etherate
488:aspect of Lewis adduct formation.
25:
1791:Modern physical organic chemistry
661:Br) as a type of Lewis acid. The
333:which is capable of accepting an
2227:Lewis, Gilbert N. (April 1916).
1649:-butylpyridine and tiny proton.
1445:from the adduct with the acid BF
1372:. Chiral Lewis bases, generally
418:{\displaystyle {\ce {(CH3)3 B}}}
53:
1869:Vollhardt, K. Peter C. (2018).
1674:BrønstedâLowry acidâbase theory
1551:BrønstedâLowry acidâbase theory
1453:favored, whereas softâsoft are
1824:Coordination Chemistry Reviews
1753:Lewis, Gilbert Newton (1923).
865:In this case, an intermediate
398:
382:
1:
2185:Journal of Chemical Education
2150:Journal of Chemical Education
1566:Reformulation of Lewis theory
1133:-system Lewis bases, such as
1959:Electrophile (Electrophilic)
1537:The concept originated with
1410:Hard and soft classification
2229:"The atom and the molecule"
1354:Applications of Lewis bases
940:Applications of Lewis acids
571:in various crystals, as in
2374:
2319:Yamamoto, Hisashi (1999).
1916:Carey, Francis A. (2003).
1413:
1396:-MeOBIPHEP), for example.
1392:uses a chiral Lewis base (
1357:
1836:10.1016/j.ccr.2015.07.018
1461:Quantifying Lewis acidity
946:FriedelâCrafts alkylation
742:Many adducts violate the
1789:Anslyn, Eric V. (2006).
1380:on a catalyst, enabling
1123:complex anions, such as
1016:amines of the formula NH
145:Self-ionization of water
130:Hammett acidity function
2062:10.1351/goldbook.H02904
1967:10.1351/goldbook.E02020
1739:10.1351/goldbook.L03508
1699:Philosophy of chemistry
1545:. In 1923, Lewis wrote
1469:and the Childs method.
1095:simple anions, such as
1689:GutmannâBeckett method
1534:
1467:Gutmann-Beckett method
1403:
631:
445:B to form an adduct NH
437:B, a lone pair from NH
419:
42:
34:Diagram of some Lewis
1684:Frustrated Lewis pair
1529:
1402:
1360:Homogeneous catalysis
626:
551:. Another example is
420:
160:Frustrated Lewis pair
120:Equilibrium chemistry
110:Dissociation constant
80:Acidâbase homeostasis
33:
1382:asymmetric catalysis
1004:such as ammonia and
569:hydrate coordination
376:
155:Lewis acid catalysis
27:Chemical bond theory
2348:Acidâbase chemistry
2304:. New York: Wiley.
2280:10.1021/ja00957a023
2245:10.1021/ja02261a002
2197:1977JChEd..54..612C
2162:1996JChEd..73..701V
1980:Inorganic Chemistry
1340:Tetrahydrothiophene
1173:
1029:where R = alkyl or
808:Complex Lewis acids
410:
397:
1669:Acidâbase reaction
1535:
1404:
1327:Trimethylphosphine
1165:
782:hexafluorosilicate
704:) are equivalent.
669:Simple Lewis acids
637:In the same vein,
632:
415:
385:
380:
75:Acidâbase reaction
43:
2358:Bases (chemistry)
2205:10.1021/ed054p612
2170:10.1021/ed073p701
2101:978-3-540-64336-4
2078:978-0-470-74957-9
2038:are referred as "
1992:10.1021/ic990713m
1986:(21): 4659â4662.
1918:Organic chemistry
1880:978-1-319-07945-1
1679:Chiral Lewis acid
1351:
1350:
1039:of the formula PR
968:, carbonium ion.
881:can be isolated.
585:magnesium sulfate
492:Depicting adducts
427:chemical reaction
413:
388:
319:
318:
165:Chiral Lewis acid
16:(Redirected from
2365:
2334:
2315:
2284:
2283:
2263:
2257:
2256:
2224:
2218:
2215:
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2112:
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2105:
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2003:
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1913:
1907:
1906:
1900:
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1840:
1839:
1819:
1813:
1812:
1786:
1780:
1770:
1750:
1741:
1718:
1664:Base (chemistry)
1543:chemical bonding
1539:Gilbert N. Lewis
1437:For example, an
1174:
1132:
987:
986:
985:
982:
963:
962:
961:
958:
928:
927:
926:
923:
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769:
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647:
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643:
609:covalent bonding
606:
598:
582:
566:
550:
536:
514:
507:
480:, emphasize the
478:electrophilicity
455:Gilbert N. Lewis
424:
422:
421:
416:
414:
411:
409:
406:
401:
396:
393:
386:
341:to form a Lewis
327:Gilbert N. Lewis
311:
304:
297:
278:Non-nucleophilic
105:Buffer solutions
90:Acidity function
57:
45:
41:
37:
21:
2373:
2372:
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2291:Further reading
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1801:
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1787:
1783:
1767:
1752:
1751:
1744:
1719:
1712:
1707:
1655:
1644:
1633:
1628:carbon monoxide
1615:
1580:coordinate bond
1568:
1524:
1512:
1508:
1504:
1500:
1492:
1488:
1484:
1480:
1463:
1448:
1418:
1412:
1406:
1386:pharmaceuticals
1370:metal catalysts
1362:
1356:
1287:
1205:
1171:
1161:
1157:
1153:
1130:
1120:
1112:
1108:
1084:has a stronger
1079:
1078:
1072:
1071:
1051:
1050:
1045:
1044:
1028:
1027:
1022:
1021:
994:
983:
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959:
956:
955:
953:
951:
942:
934:
924:
921:
920:
918:
916:
903:
901:H as Lewis acid
895:
891:
876:
873:
872:
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866:
857:
854:
853:
851:
849:
845:
837:
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560:
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549:
545:
541:
535:
531:
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523:
519:
513:
509:
505:
501:
500:â for example,
494:
474:nucleophilicity
452:
448:
444:
440:
436:
432:
374:
373:
370:Trimethylborane
362:
353:but may form a
315:
140:Proton affinity
65:Acceptor number
48:Acids and bases
39:
35:
28:
23:
22:
15:
12:
11:
5:
2371:
2369:
2361:
2360:
2355:
2350:
2340:
2339:
2336:
2335:
2329:
2316:
2310:
2292:
2289:
2286:
2285:
2274:(5): 986â992.
2258:
2239:(4): 762â785.
2219:
2210:
2175:
2140:
2127:(6): 801â808.
2107:
2100:
2082:
2065:
2022:
2005:
1970:
1941:
1926:
1908:
1879:
1861:
1841:
1814:
1799:
1781:
1765:
1742:
1709:
1708:
1706:
1703:
1702:
1701:
1696:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1654:
1651:
1642:
1631:
1614:
1611:
1567:
1564:
1523:
1520:
1515:
1514:
1510:
1506:
1502:
1498:
1490:
1486:
1482:
1478:
1462:
1459:
1446:
1441:will displace
1435:
1434:
1431:
1428:
1425:
1414:Main article:
1411:
1408:
1358:Main article:
1355:
1352:
1349:
1348:
1345:
1342:
1336:
1335:
1332:
1329:
1323:
1322:
1319:
1316:
1310:
1309:
1306:
1303:
1297:
1296:
1293:
1290:
1285:
1280:
1279:
1276:
1273:
1267:
1266:
1263:
1260:
1254:
1253:
1250:
1247:
1241:
1240:
1237:
1234:
1228:
1227:
1224:
1221:
1215:
1214:
1211:
1208:
1203:
1198:
1197:
1194:
1191:
1185:
1184:
1181:
1178:
1169:
1159:
1155:
1151:
1148:
1147:
1146:
1145:
1129:electron-rich
1127:
1121:
1118:
1110:
1106:
1103:
1086:conjugate base
1076:
1074:
1069:
1067:
1064:
1063:
1053:
1048:
1047:
1042:
1040:
1034:
1025:
1024:
1019:
1017:
993:
990:
989:
988:
973:
949:
941:
938:
937:
936:
932:
929:
914:
902:
899:
898:
897:
893:
889:
863:
862:
847:
843:
835:
830:
823:
819:
815:
809:
806:
805:
804:
789:
774:
771:
770:
755:
746:, such as the
736:
732:
728:
725:
724:
721:
717:
713:
709:
698:
697:
682:
670:
667:
658:
654:
650:
628:
620:
617:
578:
538:
537:
493:
490:
450:
446:
442:
438:
434:
430:
405:
400:
392:
384:
368:of electrons.
360:
317:
316:
314:
313:
306:
299:
291:
288:
287:
286:
285:
280:
275:
270:
265:
260:
255:
250:
248:BrønstedâLowry
242:
241:
234:
233:
232:
231:
226:
221:
216:
211:
206:
201:
196:
191:
189:BrønstedâLowry
183:
182:
175:
174:
173:
172:
167:
162:
157:
152:
147:
142:
137:
132:
127:
122:
117:
112:
107:
102:
97:
92:
87:
82:
77:
72:
67:
59:
58:
50:
49:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2370:
2359:
2356:
2354:
2351:
2349:
2346:
2345:
2343:
2332:
2330:0-19-850099-8
2326:
2322:
2317:
2313:
2311:0-471-03902-0
2307:
2303:
2299:
2295:
2294:
2290:
2281:
2277:
2273:
2269:
2262:
2259:
2254:
2250:
2246:
2242:
2238:
2234:
2230:
2223:
2220:
2214:
2211:
2206:
2202:
2198:
2194:
2190:
2186:
2179:
2176:
2171:
2167:
2163:
2159:
2155:
2151:
2144:
2141:
2135:
2130:
2126:
2122:
2118:
2111:
2108:
2103:
2097:
2093:
2086:
2083:
2079:
2075:
2069:
2066:
2063:
2059:
2055:
2051:
2050:
2045:
2041:
2037:
2031:
2029:
2027:
2023:
2019:
2018:0-7506-3365-4
2015:
2009:
2006:
2001:
1997:
1993:
1989:
1985:
1981:
1974:
1971:
1968:
1964:
1960:
1956:
1955:
1950:
1945:
1942:
1937:
1933:
1929:
1927:0-07-242458-3
1923:
1919:
1912:
1909:
1904:
1898:
1890:
1886:
1882:
1876:
1872:
1865:
1862:
1858:
1857:0-471-60180-2
1854:
1848:
1846:
1842:
1837:
1833:
1829:
1825:
1818:
1815:
1810:
1806:
1802:
1796:
1792:
1785:
1782:
1778:
1774:
1768:
1766:9780598985408
1762:
1758:
1757:
1749:
1747:
1743:
1740:
1736:
1732:
1728:
1727:
1722:
1717:
1715:
1711:
1704:
1700:
1697:
1695:
1692:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1656:
1652:
1650:
1648:
1640:
1635:
1629:
1625:
1621:
1612:
1610:
1608:
1604:
1600:
1595:
1593:
1589:
1585:
1581:
1577:
1576:covalent bond
1573:
1565:
1563:
1561:
1557:
1552:
1548:
1544:
1540:
1532:
1528:
1521:
1519:
1496:
1495:
1494:
1475:
1470:
1468:
1460:
1458:
1456:
1452:
1444:
1440:
1432:
1429:
1426:
1423:
1422:
1421:
1417:
1409:
1407:
1401:
1397:
1395:
1391:
1387:
1383:
1379:
1375:
1371:
1367:
1361:
1353:
1346:
1343:
1341:
1338:
1337:
1333:
1330:
1328:
1325:
1324:
1320:
1317:
1315:
1312:
1311:
1307:
1304:
1302:
1299:
1298:
1294:
1291:
1289:
1282:
1281:
1277:
1274:
1272:
1269:
1268:
1264:
1261:
1259:
1256:
1255:
1251:
1248:
1246:
1243:
1242:
1238:
1235:
1233:
1230:
1229:
1225:
1222:
1220:
1217:
1216:
1212:
1209:
1207:
1200:
1199:
1195:
1192:
1190:
1187:
1186:
1182:
1179:
1176:
1175:
1172:
1163:
1144:
1140:
1136:
1128:
1126:
1122:
1116:
1104:
1102:
1098:
1094:
1093:
1091:
1090:
1089:
1087:
1083:
1062:
1058:
1054:
1038:
1035:
1032:
1015:
1014:
1013:
1011:
1007:
1003:
999:
991:
971:
970:
969:
967:
966:electrophilic
947:
939:
930:
912:
911:
910:
908:
900:
887:
886:
885:
882:
841:
840:
839:
833:
826:
807:
787:
786:
785:
783:
778:
753:
752:
751:
749:
745:
740:
707:
706:
705:
703:
680:
679:
678:
676:
675:organoboranes
668:
666:
664:
635:
625:
618:
616:
614:
613:ionic bonding
610:
588:
586:
583:for hydrated
570:
554:
518:
517:
516:
499:
491:
489:
487:
486:thermodynamic
483:
479:
475:
471:
470:
465:
464:
458:
456:
428:
403:
390:
371:
367:
363:
356:
352:
348:
344:
340:
337:from a Lewis
336:
335:electron pair
332:
328:
324:
312:
307:
305:
300:
298:
293:
292:
290:
289:
284:
281:
279:
276:
274:
271:
269:
266:
264:
261:
259:
256:
254:
251:
249:
246:
245:
244:
243:
239:
235:
230:
227:
225:
222:
220:
217:
215:
212:
210:
207:
205:
202:
200:
197:
195:
192:
190:
187:
186:
185:
184:
180:
176:
171:
168:
166:
163:
161:
158:
156:
153:
151:
148:
146:
143:
141:
138:
136:
133:
131:
128:
126:
123:
121:
118:
116:
113:
111:
108:
106:
103:
101:
98:
96:
93:
91:
88:
86:
85:Acid strength
83:
81:
78:
76:
73:
71:
68:
66:
63:
62:
61:
60:
56:
52:
51:
46:
32:
19:
2320:
2301:
2298:Jensen, W.B.
2271:
2267:
2261:
2236:
2232:
2222:
2213:
2188:
2184:
2178:
2153:
2149:
2143:
2124:
2121:Can. J. Chem
2120:
2110:
2091:
2085:
2068:
2047:
2008:
1983:
1979:
1973:
1952:
1944:
1917:
1911:
1870:
1864:
1827:
1823:
1817:
1790:
1784:
1776:
1772:
1755:
1724:
1646:
1638:
1636:
1616:
1596:
1569:
1546:
1541:who studied
1536:
1516:
1471:
1464:
1436:
1419:
1405:
1393:
1374:multidentate
1363:
1232:Acetonitrile
1189:Quinuclidine
1149:
1065:
995:
943:
904:
883:
864:
811:
779:
772:
741:
726:
699:
672:
636:
633:
589:
539:
495:
477:
473:
469:electrophile
467:
461:
459:
346:
322:
320:
252:
193:
115:Donor number
2191:(10): 612.
2036:H ions
1775:, and that
1556:HSAB theory
1416:HSAB theory
1180:Donor atom
1177:Lewis base
1082:weaker acid
992:Lewis bases
619:Lewis acids
498:dative bond
463:nucleophile
355:dative bond
95:Amphoterism
2342:Categories
2156:(8): 701.
1889:1007924903
1800:1891389319
1731:Lewis acid
1705:References
1531:MO diagram
1390:mibefradil
1037:phosphines
931:H + OH â H
850:+ 2 H â 2
744:octet rule
460:The terms
429:between NH
347:Lewis base
323:Lewis acid
273:Superbases
219:Superacids
125:Extraction
18:Lewis base
1897:cite book
1830:: 59â75.
1694:ECW model
1624:protonate
1620:loss of H
1603:molecular
1474:ECW model
1457:favored.
1443:phosphine
1378:chirality
1376:, confer
972:RCl +AlCl
748:triiodide
546:B·NH
366:lone pair
170:ECW model
150:Titration
2300:(1980).
2253:95865413
2000:11671188
1936:48850987
1809:55600610
1653:See also
1592:ammonium
1560:enthalpy
1451:enthalpy
1219:Pyridine
1158:, and BF
1117:, and CH
1010:pyridine
892:â + 6 H
792:+ 2 F â
577:·7H
561:·Et
2193:Bibcode
2158:Bibcode
2042:". See
2040:protons
1584:ammonia
1522:History
1497:âÎH = E
1481:and a C
1455:entropy
1366:ligands
1301:Acetone
1143:benzene
1125:sulfate
1061:ketones
750:anion:
727:Both BF
702:ligands
524:B + :NH
482:kinetic
351:bonding
331:orbital
258:Organic
204:Organic
199:Mineral
2327:
2308:
2251:
2098:
2076:
2054:hydron
2016:
1998:
1934:
1924:
1887:
1877:
1855:
1807:
1797:
1763:
1599:atomic
1588:proton
1154:, SbCl
1141:, and
1139:ethene
1135:ethyne
1057:ethers
1002:amines
976:â R +
913:H + NH
907:proton
888:+ 6 NH
758:+ I â
731:and BF
685:+ F â
433:and Me
343:adduct
268:Strong
214:Strong
2353:Acids
2249:S2CID
2044:IUPAC
1949:IUPAC
1721:IUPAC
1572:atoms
1489:and C
1439:amine
1347:51.6
1334:97.3
1321:75.5
1314:EtOAc
1308:76.0
1295:78.8
1278:90.4
1109:O, NH
1006:alkyl
712:+ OMe
663:IUPAC
605:N â O
597:S â O
528:â Me
263:Oxide
253:Lewis
240:types
229:Solid
209:Oxide
194:Lewis
181:types
40:acids
36:bases
2325:ISBN
2306:ISBN
2096:ISBN
2074:ISBN
2014:ISBN
1996:PMID
1932:OCLC
1922:ISBN
1903:link
1885:OCLC
1875:ISBN
1853:ISBN
1805:OCLC
1795:ISBN
1761:ISBN
1659:Acid
1607:LUMO
1549:The
1472:The
1265:105
1258:DMSO
1252:112
1226:128
1213:135
1196:150
1099:and
1031:aryl
978:AlCl
954:AlCl
905:The
829:AlCl
827:and
716:â BF
611:and
599:and
573:MgSO
532:B:NH
476:and
466:and
449:â˘BMe
345:. A
339:base
283:Weak
238:Base
224:Weak
179:Acid
100:Base
70:Acid
38:and
2276:doi
2241:doi
2201:doi
2166:doi
2129:doi
2058:doi
2056:".
1988:doi
1963:doi
1961:".
1832:doi
1828:308
1735:doi
1733:".
1601:or
1513:+ W
1505:+ C
1271:THF
1245:DMA
1239:60
794:SiF
788:SiF
735:OMe
720:OMe
2344::
2272:88
2270:.
2247:.
2237:38
2235:.
2231:.
2199:.
2189:54
2187:.
2164:.
2154:73
2152:.
2125:60
2123:.
2119:.
2046:,
2025:^
1994:.
1984:38
1982:.
1951:,
1930:.
1899:}}
1895:{{
1883:.
1844:^
1826:.
1803:.
1745:^
1723:,
1713:^
1634:.
1344:S
1331:P
1318:O
1305:O
1292:O
1284:Et
1275:O
1262:O
1249:O
1236:N
1223:N
1210:N
1202:Et
1193:N
1168:BF
1162:.
1137:,
1115:HO
1113:,
1088:.
1075:pK
1068:pK
1059:,
1046:Ar
1041:3â
1018:3â
919:NH
917:â
852:BH
822:Cl
818:Al
814:Et
797:2â
784::
777:.
708:BF
687:BF
681:BF
677::
639:CH
615:.
557:BF
555:,
542:Me
520:Me
510:NH
502:Me
457:.
387:CH
359:NH
321:A
135:pH
2333:.
2314:.
2282:.
2278::
2255:.
2243::
2207:.
2203::
2195::
2172:.
2168::
2160::
2137:.
2131::
2104:.
2080:.
2060::
2020:.
2002:.
1990::
1965::
1938:.
1905:)
1891:.
1859:.
1838:.
1834::
1811:.
1769:.
1737::
1647:t
1643:3
1639:t
1632:3
1554:(
1511:B
1509:C
1507:A
1503:B
1501:E
1499:A
1491:B
1487:B
1483:A
1479:A
1477:E
1447:3
1394:R
1288:O
1286:2
1206:N
1204:3
1170:3
1160:3
1156:5
1152:2
1131:Ď
1119:3
1111:3
1107:2
1101:F
1097:H
1077:a
1070:a
1052:.
1049:x
1043:x
1026:x
1023:R
1020:x
984:4
981:â
974:3
960:4
957:â
950:3
935:O
933:2
925:4
922:+
915:3
896:O
894:2
890:3
877:7
874:â
871:H
869:2
867:B
858:4
855:â
848:6
846:H
844:2
842:B
836:3
831:3
824:3
820:2
816:3
800:6
790:4
775:2
766:3
763:â
760:I
756:2
754:I
737:2
733:3
729:4
722:2
718:3
714:2
710:3
693:4
690:â
683:3
659:3
655:N
651:3
645:3
642:+
629:3
603:3
601:R
595:2
593:R
581:O
579:2
575:4
565:O
563:2
559:3
548:3
544:3
534:3
530:3
526:3
522:3
512:3
508:â
506:B
504:3
451:3
447:3
443:3
439:3
435:3
431:3
412:B
404:3
399:)
391:3
383:(
372:(
361:3
310:e
303:t
296:v
20:)
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