544:. In essence, the reaction rates are influenced by differential solvation of the starting material and transition state by the solvent. When the reactant molecules proceed to the transition state, the solvent molecules orient themselves to stabilize the transition state. If the transition state is stabilized to a greater extent than the starting material then the reaction proceeds faster. If the starting material is stabilized to a greater extent than the transition state then the reaction proceeds slower. However, such differential solvation requires rapid reorientational relaxation of the solvent (from the transition state orientation back to the ground-state orientation). Thus, equilibrium-solvent effects are observed in reactions that tend to have sharp barriers and weakly dipolar, rapidly relaxing solvents.
289:
588:. Using a simple solvation model that considered only pure electrostatic interactions between ions or dipolar molecules and solvents in initial and transition states, all nucleophilic and elimination reactions were organized into different charge types (neutral, positively charged, or negatively charged). Hughes and Ingold then made certain assumptions about the extent of solvation to be expected in these situations:
994:
1006:
The reactions involving charged transition metal complexes (cationic or anionic) are dramatically influenced by solvation, especially in the polar media. As high as 30-50 kcal/mol changes in the potential energy surface (activation energies and relative stability) were calculated if the charge of the
552:
The equilibrium hypothesis does not stand for very rapid chemical reactions in which the transition state theory breaks down. In such cases involving strongly dipolar, slowly relaxing solvents, solvation of the transition state does not play a very large role in affecting the reaction rate. Instead,
1068:
KĂŒtt A, Movchun V, Rodima T, Dansauer T, Rusanov EB, Leito I, Kaljurand I, Koppel J, Pihl V, Koppel I, Ovsjannikov G, Toom L, Mishima M, Medebielle M, Lork E, Röschenthaler GV, Koppel IA, Kolomeitsev AA (2008). "Pentakis(trifluoromethyl)phenyl, a
Sterically Crowded and Electron-withdrawing Group:
161:
Water, being the most polar-solvent listed above, stabilizes the ionized species to a greater extent than does DMSO or
Acetonitrile. Ionization - and, thus, acidity - would be greatest in water and lesser in DMSO and Acetonitrile, as seen in the table below, which shows
634:; this fact has become increasingly more apparent as more reactions are performed in the gas phase. As such, solvent conditions significantly affect the performance of a reaction with certain solvent conditions favoring one reaction mechanism over another. For
989:
for the non-polar-solvent reaction conditions. Polar solvents stabilize the reactants to a greater extent than the non-polar-solvent conditions by solvating the negative charge on the nucleophile, making it less available to react with the electrophile.
837:). There is a noticeable increase in reaction rate when changing from a protic solvent to an aprotic solvent. This difference arises from acid/base reactions between protic solvents (not aprotic solvents) and strong nucleophiles. While it is true that
512:
Often, reactivity and reaction mechanisms are pictured as the behavior of isolated molecules in which the solvent is treated as a passive support. However, the nature of the solvent can actually influence reaction rates and order of a chemical reaction.
650:
1 reactions is a result of the polar solvent's solvating the reactant intermediate species, i.e., the carbocation, thereby decreasing the intermediate energy relative to the starting material. The following table shows the relative solvolysis rates of
820:
react with strong nucleophiles with good basic character in an acid/base fashion, thus decreasing or removing the nucleophilic nature of the nucleophile. The following table shows the effect of solvent polarity on the relative reaction rates of the
81:
of a reaction by differential stabilization of the reactant or product. The equilibrium is shifted in the direction of the substance that is preferentially stabilized. Stabilization of the reactant or product can occur through any of the different
811:
1 reaction mechanisms are viable is the strength of the
Nucleophile. Nuclephilicity and basicity are linked and the more nucleophilic a molecule becomes the greater said nucleophile's basicity. This increase in basicity causes problems for
1140:
Kaljurand I, KĂŒtt A, SoovĂ€li L, Rodima T, MĂ€emets V, Leito I, Koppel IA (2005). "Extension of the Self-Consistent
Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales".
1340:
Hughes, Edward D.; Ingold, Christopher K. (1935). "Mechanism of substitution at a saturated carbon atom. Part IV. A discussion of constitutional and solvent effects on the mechanism, kinetics, velocity, and orientation of substitution".
972:
for the polar-solvent reaction conditions. This arises from the fact that polar solvents stabilize the formation of the carbocation intermediate to a greater extent than the non-polar-solvent conditions. This is apparent in the
1104:
KĂŒtt, A.; Leito, I.; Kaljurand, I.; SoovĂ€li, L.; Vlasov, V.M.; Yagupolskii, L.M.; Koppel, I.A. (2006). "A Comprehensive Self-Consistent
Spectrophotometric Acidity Scale of Neutral BrĂžnsted Acids in Acetonitrile".
106:
and its ability to preferentially solvate and thus stabilize certain species in acid-base equilibria. A change in the solvating ability or dielectric constant can thus influence the acidity or basicity.
444:
612:
A change in solvent polarity will have little or no effect on the rates of reaction when there is little or no difference in charge between the reactants and the activated complex.
102:
The ionization equilibrium of an acid or a base is affected by a solvent change. The effect of the solvent is not only because of its acidity or basicity but also because of its
1440:
V. P. Ananikov; D. G. Musaev; K. Morokuma (2001). "Catalytic Triple Bond
Activation and VinylâVinyl Reductive Coupling by Pt(IV) Complexes. A Density Functional Study".
1015:
Many free radical-based syntheses show large kinetic solvent effects that can reduce the rate of reaction and cause a planned reaction to follow an unwanted pathway.
606:
An increase in solvent polarity accelerates the rates of reactions where a charge is developed in the activated complex from neutral or slightly charged reactant
1524:
532:
techniques where physical methods are used to control reactions rather than solvents are methods are methods for affecting reactions in the absence of solvent.
59:
609:
An increase in solvent polarity decreases the rates of reactions where there is less charge in the activated complex in comparison to the starting materials
1377:
1324:
1736:
1613:
1570:
1877:
1517:
1249:
1220:
1053:
993:
1312:
1468:
351:
1785:
1780:
1590:
1945:
1950:
580:
The effect of solvent on elimination and nucleophillic substitution reactions was originally studied by
British chemists
1976:
1510:
646:
is of direct importance to its viability as a suitable solvent. The ability of polar solvents to increase the rate of S
1971:
336:
H-bonding with the solvent. As a result, solvents of low polarity that do not readily participate in H-bonding allow
1915:
1605:
1241:
305:
1642:
1542:
1369:
574:
1872:
791:
and thereby increase the rate of the reaction. This relationship is according to the equation ÎG = âRT ln K (
1920:
1721:
585:
541:
69:
dissolves in a solvent when solvent-solute interactions are more favorable than solute-solute interaction.
1675:
841:
also affect the relative reaction rates, however, for demonstration of principle for solvent polarity on S
627:
199:
1393:
Yongho, Kim.; Cramer, Christopher J.; Truhlar, Donald G. (2009). "Steric
Effects and Solvent Effects on S
1905:
1837:
1695:
1685:
540:
Solvents can affect rates through equilibrium-solvent effects that can be explained on the basis of the
1900:
1628:
1406:
1274:
325:
317:
83:
78:
309:
149:
In the table above, it can be seen that water is the most polar-solvent, followed by DMSO, and then
1910:
1842:
1827:
1770:
1316:
652:
103:
91:
43:
1935:
1705:
1534:
324:-enol form predominating at low polarity and the diketo form predominating at high polarity. The
51:
803:
being first order in
Nucleophile and first order in Reagent. The determining factor when both S
1930:
1925:
1887:
1832:
1751:
1731:
1667:
1488:
1422:
1373:
1320:
1245:
1216:
1158:
1122:
1086:
1049:
792:
218:
1069:
Synthesis and
Acidity of Pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline".
1862:
1811:
1765:
1480:
1449:
1414:
1346:
1304:
1282:
1150:
1114:
1078:
581:
313:
1940:
1852:
817:
767:
is quite different, as the lack of solvation on the nucleophile increases the rate of an S
529:
1305:
1410:
1286:
1278:
602:
The applicable effect of these general assumptions are shown in the following examples:
288:
1647:
1636:
838:
333:
1965:
1895:
1867:
1775:
1726:
1700:
826:
521:
169:
values at 25 °C for acetonitrile (ACN) and dimethyl sulfoxide (DMSO) and water.
87:
55:
1847:
1653:
1560:
1550:
760:
635:
525:
234:
150:
17:
516:
Performing a reaction without solvent can affect reaction-rate for reactions with
1176:
1806:
1741:
1024:
800:
659:
643:
631:
517:
250:
47:
1857:
1502:
1212:
562:
31:
1492:
1469:"The frequently overlooked importance of solvent in free radical syntheses"
1426:
1162:
1126:
1090:
1350:
671:
598:
loss of charge will decrease solvation more than the dispersal of charge
554:
301:
1484:
558:
39:
1453:
1418:
1154:
1118:
1082:
1048:(4th ed.), New York: Oxford University Press, pp. 317â318,
266:
66:
1760:
830:
679:
287:
1265:
James T. Hynes (1985). "Chemical Reaction Dynamics in Solution".
1506:
332:-enol form is more pronounced when there is no competition for
1580:
1467:
Grzegorz Litwinienko; A. L. J. Beckwith; K. U. Ingold (2011).
1007:
metal species was changed during the chemical transformation.
27:
Influence of a solvent on chemical reactivity, stability, etc.
816:
2 reaction mechanisms when the solvent of choice is protic.
992:
779:
2), the ability to either stabilize the transition state (S
439:{\displaystyle {\mathbf {K} }_{\mathrm {T} }={\frac {}{}}}
46:
or molecular associations. Solvents can have an effect on
153:. Consider the following acid dissociation equilibrium:
968:
1 reaction coordinate diagram. Note the decrease in ÎG
592:
increasing magnitude of charge will increase solvation
985:
2 reaction coordinate diagram. Note the decreased ÎG
354:
1307:
Advanced Organic Chemistry: Structure and Mechanisms
642:
the solvent's ability to stabilize the intermediate
565:) play a large role in affecting the reaction rate.
1886:
1820:
1794:
1750:
1714:
1666:
1627:
1604:
1541:
845:2 reaction rates, steric effects may be neglected.
783:
1) or destabilize the reactant starting material (S
340:-enolic stabilization by intramolecular H-bonding.
438:
964:2 reactions is to the right. On the left is an S
630:inherently determines the nucleophilicity of the
595:increasing delocalization will decrease solvation
320:is dependent upon the solvent polarity, with the
1303:Sundberg, Richard J.; Carey, Francis A. (2007).
292:Keto enol tautomerization (diketo form on left,
58:and choosing the appropriate solvent allows for
553:dynamic contributions of the solvent (such as
1518:
8:
1202:
1200:
1198:
1196:
1194:
1192:
520:mechanisms, for example, by maximizing the
1525:
1511:
1503:
1366:Organic Chemistry Structure and Reactivity
1238:Physical and Mechanistic Organic Chemistry
308:. This effect is especially pronounced in
374:
364:
363:
357:
356:
353:
997:Solvent effects on SN1 and SN2 reactions
847:
688:
342:
171:
109:
1298:
1296:
1036:
1551:Unimolecular nucleophilic substitution
1177:"Bordwell pKa Table (Acidity in DMSO)"
1561:Bimolecular nucleophilic substitution
7:
1209:Solvent Effects in Organic Chemistry
1002:Transition-metal-catalyzed reactions
1614:Electrophilic aromatic substitution
1287:10.1146/annurev.pc.36.100185.003041
1581:Nucleophilic internal substitution
1571:Nucleophilic aromatic substitution
365:
77:Different solvents can affect the
25:
111:Solvent properties at 25 °C
60:thermodynamic and kinetic control
358:
1737:LindemannâHinshelwood mechanism
1786:Outer sphere electron transfer
1781:Inner sphere electron transfer
1591:Nucleophilic acyl substitution
430:
409:
404:
377:
90:, dipole-dipole interactions,
1:
1951:Diffusion-controlled reaction
1207:Reichardt, Christian (1990).
771:2 reaction. In either case (S
1606:Electrophilic substitutions
795:). The rate equation for S
536:Equilibrium-solvent effects
1993:
1916:Energy profile (chemistry)
1878:More O'FerrallâJencks plot
1543:Nucleophilic substitutions
1242:Cambridge University Press
787:2) acts to decrease the ÎG
572:
548:Frictional solvent effects
92:van der Waals interactions
62:over a chemical reaction.
1946:MichaelisâMenten kinetics
1370:Houghton Mifflin Harcourt
508:Effects on reaction rates
86:with the solvent such as
84:non-covalent interactions
1873:Potential energy surface
1752:Electron/Proton transfer
1637:Unimolecular elimination
1044:Loudon, G. Marc (2005),
573:Not to be confused with
561:, internal pressure, or
312:compounds that can form
1921:Transition state theory
1722:Intramolecular reaction
1648:Bimolecular elimination
1236:Jones, Richard (1984).
981:. On the right is an S
586:Christopher Kelk Ingold
542:transition state theory
38:are the influence of a
1715:Unimolecular reactions
1676:Electrophilic addition
1011:Free radical syntheses
998:
857:Dielectric Constant, Δ
698:Dielectric Constant, Δ
628:substitution reactions
622:Substitution reactions
440:
297:
1906:Rate-determining step
1838:Reactive intermediate
1696:Free-radical addition
1686:Nucleophilic addition
1629:Elimination reactions
1267:Annu. Rev. Phys. Chem
996:
441:
328:H-bond formed in the
306:ketoâenol tautomerism
291:
203:-Toluenesulfonic acid
1901:Equilibrium constant
1364:EÄe, Seyhan (2008).
1351:10.1039/JR9350000244
1215:. pp. 147â181.
1211:. Marburg, Germany:
626:The solvent used in
575:HughesâIngold symbol
352:
318:equilibrium constant
296:-enol form on right)
284:Ketoâenol equilibria
119:Dielectric constant
98:Acid-base equilibria
79:equilibrium constant
73:Effects on stability
1977:Reaction mechanisms
1911:Reaction coordinate
1843:Radical (chemistry)
1828:Elementary reaction
1771:Grotthuss mechanism
1535:reaction mechanisms
1411:2009JPCA..113.9109K
1279:1985ARPC...36..573H
1244:. pp. 94â114.
569:HughesâIngold rules
181:
112:
104:dielectric constant
44:chemical reactivity
18:HughesâIngold rules
1972:Physical chemistry
1936:Arrhenius equation
1706:Oxidative addition
1668:Addition reactions
1485:10.1039/C1CS15007C
999:
528:is one of several
436:
304:compounds exhibit
298:
172:
110:
1959:
1958:
1931:Activated complex
1926:Activation energy
1888:Chemical kinetics
1833:Reaction dynamics
1732:Photodissociation
1454:10.1021/om001073u
1419:10.1021/jp905429p
1405:(32): 9109â9114.
1379:978-0-618-31809-4
1326:978-0-387-44897-8
1155:10.1021/jo048252w
1119:10.1021/jo060031y
1083:10.1021/jo702513w
1046:Organic Chemistry
956:A comparison of S
954:
953:
793:Gibbs free energy
757:
756:
617:Reaction examples
524:of the reagents.
505:
504:
434:
281:
280:
219:2,4-Dinitrophenol
147:
146:
132:Dimethylsulfoxide
16:(Redirected from
1984:
1863:Collision theory
1812:Matrix isolation
1766:Harpoon reaction
1643:E1cB-elimination
1527:
1520:
1513:
1504:
1497:
1496:
1464:
1458:
1457:
1448:(8): 1652â1667.
1437:
1431:
1430:
1399:J. Phys. Chem. A
1390:
1384:
1383:
1361:
1355:
1354:
1337:
1331:
1330:
1310:
1300:
1291:
1290:
1262:
1256:
1255:
1233:
1227:
1226:
1204:
1187:
1186:
1184:
1183:
1173:
1167:
1166:
1149:(3): 1019â1028.
1137:
1131:
1130:
1113:(7): 2829â2838.
1101:
1095:
1094:
1077:(7): 2607â2620.
1065:
1059:
1058:
1041:
848:
799:2 reactions are
689:
582:Edward D. Hughes
445:
443:
442:
437:
435:
433:
407:
375:
370:
369:
368:
362:
361:
343:
182:
180:values of acids
113:
21:
1992:
1991:
1987:
1986:
1985:
1983:
1982:
1981:
1962:
1961:
1960:
1955:
1941:Eyring equation
1882:
1853:Stereochemistry
1816:
1802:Solvent effects
1790:
1746:
1710:
1691:
1681:
1662:
1657:
1623:
1619:
1600:
1596:
1586:
1576:
1566:
1556:
1537:
1531:
1501:
1500:
1466:
1465:
1461:
1442:Organometallics
1439:
1438:
1434:
1396:
1392:
1391:
1387:
1380:
1363:
1362:
1358:
1339:
1338:
1334:
1327:
1302:
1301:
1294:
1264:
1263:
1259:
1252:
1235:
1234:
1230:
1223:
1206:
1205:
1190:
1181:
1179:
1175:
1174:
1170:
1139:
1138:
1134:
1103:
1102:
1098:
1067:
1066:
1062:
1056:
1043:
1042:
1038:
1033:
1021:
1013:
1004:
988:
984:
980:
976:
971:
967:
963:
959:
940:
894:
876:
844:
836:
824:
818:Protic solvents
815:
810:
806:
798:
790:
786:
782:
778:
774:
770:
764:
746:
731:
716:
712:
685:
677:
669:
665:
656:-butyl chloride
649:
639:
624:
619:
578:
571:
550:
538:
530:mechanochemical
510:
490:Dichloromethane
466:Tetrahydrofuran
408:
376:
355:
350:
349:
314:hydrogen-bonded
286:
179:
168:
100:
75:
36:solvent effects
28:
23:
22:
15:
12:
11:
5:
1990:
1988:
1980:
1979:
1974:
1964:
1963:
1957:
1956:
1954:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1903:
1898:
1892:
1890:
1884:
1883:
1881:
1880:
1875:
1870:
1865:
1860:
1855:
1850:
1845:
1840:
1835:
1830:
1824:
1822:
1821:Related topics
1818:
1817:
1815:
1814:
1809:
1804:
1798:
1796:
1795:Medium effects
1792:
1791:
1789:
1788:
1783:
1778:
1773:
1768:
1763:
1757:
1755:
1748:
1747:
1745:
1744:
1739:
1734:
1729:
1724:
1718:
1716:
1712:
1711:
1709:
1708:
1703:
1698:
1693:
1689:
1683:
1679:
1672:
1670:
1664:
1663:
1661:
1660:
1655:
1651:
1645:
1640:
1633:
1631:
1625:
1624:
1622:
1621:
1617:
1610:
1608:
1602:
1601:
1599:
1598:
1594:
1588:
1584:
1578:
1574:
1568:
1564:
1558:
1554:
1547:
1545:
1539:
1538:
1532:
1530:
1529:
1522:
1515:
1507:
1499:
1498:
1479:(5): 2157â63.
1473:Chem. Soc. Rev
1459:
1432:
1397:2 Reactions".
1394:
1385:
1378:
1356:
1332:
1325:
1292:
1273:(1): 573â597.
1257:
1250:
1228:
1221:
1188:
1168:
1132:
1096:
1060:
1054:
1035:
1034:
1032:
1029:
1028:
1027:
1020:
1017:
1012:
1009:
1003:
1000:
986:
982:
978:
974:
969:
965:
961:
957:
952:
951:
948:
945:
942:
938:
934:
933:
930:
927:
924:
920:
919:
916:
913:
910:
906:
905:
902:
899:
896:
892:
888:
887:
884:
881:
878:
874:
870:
869:
864:
859:
854:
842:
839:steric effects
834:
825:2 reaction of
822:
813:
808:
804:
796:
788:
784:
780:
776:
772:
768:
762:
755:
754:
751:
748:
744:
740:
739:
736:
733:
729:
725:
724:
721:
718:
714:
710:
706:
705:
700:
695:
683:
675:
667:
663:
647:
637:
623:
620:
618:
615:
614:
613:
610:
607:
600:
599:
596:
593:
570:
567:
549:
546:
537:
534:
509:
506:
503:
502:
499:
495:
494:
491:
487:
486:
483:
479:
478:
475:
471:
470:
467:
463:
462:
459:
455:
454:
451:
447:
446:
432:
429:
426:
423:
420:
417:
414:
411:
406:
403:
400:
397:
394:
391:
388:
385:
382:
379:
373:
367:
360:
347:
334:intermolecular
326:intramolecular
310:1,3-dicarbonyl
285:
282:
279:
278:
275:
272:
269:
263:
262:
259:
256:
253:
247:
246:
243:
240:
237:
231:
230:
227:
224:
221:
215:
214:
211:
208:
205:
196:
195:
192:
189:
186:
177:
166:
159:
158:
145:
144:
141:
137:
136:
133:
129:
128:
125:
121:
120:
117:
99:
96:
74:
71:
56:reaction rates
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1989:
1978:
1975:
1973:
1970:
1969:
1967:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1896:Rate equation
1894:
1893:
1891:
1889:
1885:
1879:
1876:
1874:
1871:
1869:
1868:Arrow pushing
1866:
1864:
1861:
1859:
1856:
1854:
1851:
1849:
1846:
1844:
1841:
1839:
1836:
1834:
1831:
1829:
1826:
1825:
1823:
1819:
1813:
1810:
1808:
1805:
1803:
1800:
1799:
1797:
1793:
1787:
1784:
1782:
1779:
1777:
1776:Marcus theory
1774:
1772:
1769:
1767:
1764:
1762:
1759:
1758:
1756:
1753:
1749:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1727:Isomerization
1725:
1723:
1720:
1719:
1717:
1713:
1707:
1704:
1702:
1701:Cycloaddition
1699:
1697:
1694:
1687:
1684:
1677:
1674:
1673:
1671:
1669:
1665:
1659:
1652:
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1589:
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1579:
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1569:
1562:
1559:
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1474:
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1420:
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1343:J. Chem. Soc.
1336:
1333:
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907:
903:
900:
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890:
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868:
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863:
862:Relative Rate
860:
858:
855:
853:
850:
849:
846:
840:
832:
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827:1-bromobutane
819:
802:
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752:
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734:
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726:
722:
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707:
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703:Relative Rate
701:
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681:
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657:
655:
645:
641:
633:
629:
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522:concentration
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489:
488:
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424:
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412:
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398:
395:
392:
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386:
383:
380:
371:
348:
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327:
323:
319:
315:
311:
307:
303:
295:
290:
283:
276:
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241:
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220:
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212:
209:
206:
204:
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197:
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190:
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184:
183:
176:
170:
165:
156:
155:
154:
152:
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139:
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130:
126:
123:
122:
118:
115:
114:
108:
105:
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95:
93:
89:
85:
80:
72:
70:
68:
63:
61:
57:
53:
49:
45:
41:
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33:
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1848:Molecularity
1801:
1476:
1472:
1462:
1445:
1441:
1435:
1402:
1398:
1388:
1365:
1359:
1342:
1335:
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1306:
1270:
1266:
1260:
1237:
1231:
1208:
1180:. Retrieved
1171:
1146:
1143:J. Org. Chem
1142:
1135:
1110:
1107:J. Org. Chem
1106:
1099:
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1071:J. Org. Chem
1070:
1063:
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1014:
1005:
955:
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861:
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851:
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697:
692:
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625:
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579:
551:
539:
526:Ball milling
515:
511:
337:
329:
321:
299:
293:
235:Benzoic acid
200:
174:
163:
160:
151:acetonitrile
148:
124:Acetonitrile
101:
76:
64:
35:
29:
1807:Cage effect
1742:RRKM theory
1658:elimination
1345:: 244â255.
1315:. pp.
1025:Cage effect
801:bimolecular
765:2 reactions
660:acetic acid
644:carbocation
640:1 reactions
632:nucleophile
518:bimolecular
458:Cyclohexane
316:enols. The
251:Acetic acid
1966:Categories
1182:2008-11-02
1031:References
987:activation
979:activation
970:activation
789:activation
185:HA â A + H
157:HA â A + H
48:solubility
1858:Catalysis
1754:reactions
1213:Wiley-VCH
678:OH), and
563:viscosity
450:Gas phase
390:−
88:H-bonding
52:stability
32:chemistry
1493:21344074
1427:19719294
1313:Springer
1163:15675863
1127:16555839
1091:18324831
1019:See also
950:Aprotic
932:Aprotic
918:Aprotic
753:150,000
672:methanol
555:friction
302:carbonyl
1407:Bibcode
1275:Bibcode
904:Protic
886:Protic
852:Solvent
807:2 and S
693:Solvent
559:density
482:Ethanol
474:Benzene
346:Solvent
213:strong
116:Solvent
40:solvent
1533:Basic
1491:
1425:
1376:
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1319:â376.
1248:
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960:1 to S
775:1 or S
267:Phenol
261:4.756
194:water
67:solute
1761:Redox
1597:Acyl)
977:, ÎÎG
915:1,300
831:azide
829:with
680:water
658:with
501:0.23
498:Water
477:14.7
453:11.7
300:Many
277:9.99
271:29.14
255:23.51
239:21.51
223:16.66
140:Water
94:etc.
1650:(E2)
1639:(E1)
1489:PMID
1423:PMID
1374:ISBN
1321:ISBN
1246:ISBN
1217:ISBN
1159:PMID
1123:PMID
1087:PMID
1050:ISBN
947:5000
929:2800
909:DMSO
867:Type
686:O).
670:H),
654:tert
584:and
493:4.2
485:5.8
469:7.2
274:18.0
258:12.6
245:4.2
242:11.1
229:3.9
191:DMSO
54:and
1620:Ar)
1577:Ar)
1481:doi
1450:doi
1415:doi
1403:113
1347:doi
1317:359
1283:doi
1151:doi
1115:doi
1079:doi
923:DMF
674:(CH
662:(CH
461:42
338:cis
330:cis
322:cis
294:cis
226:5.1
210:0.9
207:8.5
188:ACN
143:78
135:47
127:37
42:on
30:In
1968::
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1678:(A
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1471:.
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1121:.
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912:49
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880:33
877:OH
873:CH
833:(N
750:78
738:4
735:33
732:OH
728:CH
723:1
713:CO
709:CH
682:(H
666:CO
557:,
65:A
50:,
34:,
1692:)
1690:N
1682:)
1680:E
1656:i
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1555:N
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1483::
1456:.
1452::
1429:.
1417::
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1353:.
1349::
1329:.
1289:.
1285::
1277::
1254:.
1225:.
1185:.
1165:.
1153::
1129:.
1117::
1093:.
1081::
983:N
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966:N
962:N
958:N
939:3
901:7
895:O
893:2
891:H
883:1
875:3
843:N
835:3
823:N
821:S
814:N
812:S
809:N
805:N
797:N
785:N
781:N
777:N
773:N
769:N
763:N
761:S
747:O
745:2
743:H
730:3
720:6
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711:3
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676:3
668:2
664:3
648:N
638:N
636:S
577:.
431:]
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419:k
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413:d
410:[
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402:l
399:o
396:n
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381:c
378:[
372:=
366:T
359:K
201:p
178:a
175:K
173:p
167:a
164:K
162:p
20:)
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