780:
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894:
518:
31:
1284:
Goto, Kei; Nagahama, Michiko; Mizushima, Tadashi; Shimada, Keiichi; Kawashima, Takayuki; Okazaki, Renji (2001). "The First Direct
Oxidative Conversion of a Selenol to a Stable Selenenic Acid: Experimental Demonstration of Three Processes Included in the Catalytic Cycle of Glutathione Peroxidase".
779:
821:
53:
arise from the spatial arrangement of atoms. When atoms come close together there is generally a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape (
1184:
Helmut Fiege; Heinz-Werner Voges; Toshikazu
Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2002). "Phenol Derivatives".
760:
1251:
Klaus Köhler; Peter
Simmendinger; Wolfgang Roelle; Wilfried Scholz; Andreas Valet; Mario Slongo (2010). "Paints and Coatings, 4. Pigments, Extenders, and Additives".
863:
380:
345:
318:
151:
Relative rates of chemical reactions provide useful insights into the effects of the steric bulk of substituents. Under standard conditions, methyl bromide
848:
766:
1268:
1234:
1124:
1039:
108:
is a consequence of steric effects. Steric hindrance is the slowing of chemical reactions due to steric bulk. It is usually manifested in
882:
143:
Because steric effects have profound impact on properties, the steric properties of substituents have been assessed by numerous methods.
1366:
1323:
1201:
1140:
Tolman, Chadwick A. (1970-05-01). "Phosphorus ligand exchange equilibriums on zerovalent nickel. Dominant role for steric effects".
1058:
1008:
1167:
Stephan, Douglas W. "Frustrated Lewis pairs": a concept for new reactivity and catalysis. Org. Biomol. Chem. 2008, 6, 1535–1539.
854:
182:
provide another measure of the bulk of substituents. A-values are derived from equilibrium measurements of monosubstituted
797:
940:
201:
above. It costs 1.74 kcal/mol for the methyl group to adopt to the axial position compared to the equatorial position.
1337:
728:. In organic chemistry, steric effects are nearly universal and affect the rates and activation energies of most
69:
result in structured groupings of molecules stabilized by the way that opposites attract and like charges repel.
946:
1361:
54:
827:
785:
770:
648:
533:
1029:
869:
812:
793:
116:. Steric hindrance is often exploited to control selectivity, such as slowing unwanted side-reactions.
1053:
E.L. Eliel, S.H. Wilen and L.N. Mander, Stereochemistry of
Organic Compounds, Wiley, New York (1994).
972:
Günther Maier; Stephan Pfriem; Ulrich Schäfer; Rudolf
Matusch (1978). "Tetra-tert-butyltetrahedrane".
540:
formed with the metal at the vertex and the hydrogen atoms at the perimeter of the cone (see figure).
951:
935:
198:
574:
495:
290:
65:, which dictate the shape and reactivity of molecules. Steric repulsive forces between overlapping
627:
591:
62:
916:
cation, difficult. It is difficult for electrophiles to get close enough to allow attack by the
89:
in the presence of a free secondary 3'-hydroxy group as a result of steric hindrance due to the
1302:
1264:
1230:
1197:
1142:
1120:
1054:
1035:
1004:
873:
729:
525:
156:
58:
39:
735:
In biochemistry, steric effects are often exploited in naturally occurring molecules such as
186:. The extent that a substituent favors the equatorial position gives a measure of its bulk.
179:
159:. The difference reflects the inhibition of attack on the compound with the sterically bulky
1294:
1256:
1222:
1217:
Pieter
Gijsman (2010). "Photostabilisation of Polymer Materials". In Norman S. Allen (ed.).
1189:
1168:
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789:
352:
77:
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323:
296:
1345:
1331:
189:
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348:
66:
35:
1355:
439:
906:
725:
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320:) is a measure of the steric properties of the monomers that comprise a polymer.
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537:
419:
183:
1226:
893:
748:
160:
152:
132:
120:
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917:
747:
structure. In pharmacology, steric effects determine how and at what rate a
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717:
561:
545:
86:
27:
Geometric aspects of ions and molecules affecting their shape and reactivity
1306:
985:
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459:
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128:
124:
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1119:(3rd ed.). New York: Oxford University Press. pp. 193–194.
736:
529:
194:
94:
1104:(fourth ed.). New York: John Wiley & Sons, Inc. p. 40.
1089:(first ed.). New York: John Wiley & Sons, Inc. p. 199.
1219:
Photochemistry and
Photophysics of Polymer Materials Photochemistry
517:
119:
Steric hindrance between adjacent groups can also affect torsional
1070:
Eliel, E.L.; Allinger, N.L.; Angyal, S.J.; G.A., Morrison (1965).
910:
902:
898:
892:
188:
1031:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
355:
are equal. Sterically hindered monomers give polymers with low
30:
945:
Reaction rate accelerate as result of steric hindrance in the
1338:
Steric: A Program to
Calculate the Steric Size of Molecules (
123:. Steric hindrance is responsible for the observed shape of
831:
1100:
Romers, C.; Altona, C.; Buys, H.R.; Havinga, E. (1969).
842:-based products ranging from petrochemicals to plastics.
127:
and the low rates of racemization of 2,2'-disubstituted
888:
An isolable selenenic acid owing to steric protection.
112:, whereas discussion of steric effects often focus on
81:
Regioselective dimethoxytritylation of the primary 5'-
361:
326:
299:
1221:. Hoboken: John Wiley & Sons. pp. 627–679.
374:
339:
312:
61:of ions and molecules. Steric effects complement
1001:Oligonucleotide synthesis: a practical approach
1253:Ullmann's Encyclopedia Of Industrial Chemistry
1186:Ullmann's Encyclopedia of Industrial Chemistry
1034:(6th ed.), New York: Wiley-Interscience,
751:will interact with its target bio-molecules.
8:
920:of the nitrogen (nitrogen is shown in blue)
1188:. Weinheim: Wiley-VCH. pp. a19_313.
366:
360:
331:
325:
304:
298:
542:
516:
384:
204:
76:
29:
964:
755:Prominent sterically hindered compounds
753:
767:Tris(2,4-di-tert-butylphenyl)phosphite
347:is the temperature where the rate of
7:
1074:. New York: Interscience Publishers.
743:site may be buried within a large
382:'s, which are usually not useful.
197:group is 1.74 as derived from the
25:
1348: (archived December 22, 2017)
1117:Polymer Chemistry an Introduction
1115:Stevens, Malcolm P. (1999). "6".
909:reactions, like forming the tetra
881:
872:is a monomer, the corresponding
862:
855:Hindered amine light stabilizers
847:
820:
778:
759:
897:The steric effect of tri-(tert-
716:Steric effects are critical to
1:
1334: (archived July 25, 2008)
954:, also known as steric strain
712:Significance and applications
139:Measures of steric properties
941:Sterically induced reduction
857:are widely used in polymers.
528:are measures of the size of
46:-butyl derivative is robust.
114:intramolecular interactions
1383:
1367:Physical organic chemistry
1227:10.1002/9780470594179.ch17
974:Angew. Chem. Int. Ed. Engl
1102:Topics in Stereochemistry
1087:Topics in Stereochemistry
1261:10.1002/14356007.o18_o03
1194:10.1002/14356007.a19_313
830:is used industrially as
811:, comprises the classic
536:. It is defined as the
391:Ceiling temperature (°C)
110:intermolecular reactions
1072:Conformational Analysis
828:2,6-Di-tert-butylphenol
999:Gait, Michael (1984).
986:10.1002/anie.197805201
921:
786:Tricyclohexylphosphine
544:Cone angles of common
534:coordination chemistry
522:
376:
341:
314:
202:
102:
47:
1085:Hirsch, J.A. (1967).
1003:. Oxford: IRL Press.
896:
870:Titanium isopropoxide
813:frustrated Lewis pair
794:homogeneous catalysis
520:
377:
375:{\displaystyle T_{c}}
342:
340:{\displaystyle T_{c}}
315:
313:{\displaystyle T_{c}}
192:
80:
33:
1255:. pp. o18_o03.
952:Van der Waals strain
947:Thorpe–Ingold effect
936:Intramolecular force
732:to varying degrees.
359:
324:
297:
286:Ceiling temperatures
199:chemical equilibrium
155:10 faster than does
1155:10.1021/ja00713a007
1024:Smith, Michael B.;
549:
291:Ceiling temperature
922:
730:chemical reactions
543:
526:Ligand cone angles
523:
521:Ligand cone angle.
372:
337:
310:
203:
193:The A-value for a
103:
63:electronic effects
48:
1299:10.1021/ol016682s
1293:(22): 3569–3572.
1270:978-3-527-30673-2
1236:978-0-470-59417-9
1149:(10): 2956–2965.
1143:J. Am. Chem. Soc.
1126:978-0-19-512444-6
1041:978-0-471-72091-1
874:titanium ethoxide
709:
708:
510:
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157:neopentyl bromide
16:(Redirected from
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73:Steric hindrance
38:(R = H) readily
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1362:Stereochemistry
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51:Steric effects
36:cyclobutadiene
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1019:
1000:
994:
980:(7): 520–1.
977:
973:
967:
836:antioxidants
773:in polymers.
739:, where the
734:
726:pharmacology
722:biochemistry
715:
670:
524:
289:
213:
208:
184:cyclohexanes
178:
150:
142:
118:
113:
109:
105:
104:
55:conformation
50:
49:
43:
42:but the R =
840:hydrocarbon
538:solid angle
513:Cone angles
471:=C(Me)CH=CH
420:isobutylene
209:Substituent
121:bond angles
97:ring (Py =
34:The parent
1356:Categories
959:References
796:and, with
788:, a bulky
771:stabilizer
556:Angle (°)
503:PhC(Me)=CH
394:Structure
153:solvolyzes
133:binaphthyl
59:reactivity
918:lone pair
741:catalytic
718:chemistry
649:P(cyclo-C
546:phosphine
147:Rate data
125:rotaxanes
87:thymidine
85:group of
40:dimerizes
1307:11678710
1028:(2007),
925:See also
914:ammonium
792:used in
684:P(2,4,6-
548:ligands
460:isoprene
451:=CHCH=CH
400:ethylene
180:A-values
175:A-values
129:biphenyl
99:pyridine
83:hydroxyl
18:Hindered
1344:at the
1330:at the
745:protein
737:enzymes
530:ligands
487:PhCH=CH
480:styrene
388:Monomer
214:A-Value
171:group.
1305:
1267:
1233:
1200:
1123:
1057:
1038:
1007:
905:makes
724:, and
553:Ligand
279:>4
195:methyl
95:ribose
57:) and
911:alkyl
903:amine
899:butyl
575:P(OCH
264:2.15
254:CH(CH
249:1.75
234:1.74
1303:PMID
1265:ISBN
1231:ISBN
1198:ISBN
1121:ISBN
1055:ISBN
1036:ISBN
1005:ISBN
838:for
749:drug
705:212
679:182
673:-Bu)
664:179
643:145
622:132
608:P(CH
603:118
592:P(CH
586:107
431:=CMe
351:and
269:C(CH
131:and
44:tert
1295:doi
1257:doi
1223:doi
1190:doi
1169:doi
1151:doi
982:doi
798:B(C
628:P(C
569:87
532:in
484:395
464:466
444:585
424:175
411:=CH
404:610
161:(CH
1358::
1301:.
1289:.
1263:.
1229:.
1196:.
1147:92
978:17
976:.
832:UV
720:,
686:Me
669:P(
655:11
612:CH
562:PH
500:66
467:CH
447:CH
427:CH
407:CH
243:CH
239:CH
228:CH
223:0
101:).
1342:)
1328:)
1309:.
1297::
1291:3
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1239:.
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1192::
1171::
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1153::
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984::
901:)
815:.
808:3
806:)
804:5
802:F
800:6
701:3
699:)
696:2
694:H
692:6
690:C
688:3
675:3
671:t
659:3
657:)
653:H
651:6
638:3
636:)
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632:H
630:6
618:3
616:)
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610:2
598:3
596:)
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489:2
473:2
469:2
453:2
449:2
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429:2
413:2
409:2
368:c
364:T
333:c
329:T
306:c
302:T
293:(
275:3
273:)
271:3
260:2
258:)
256:3
245:3
241:2
230:3
220:H
169:C
167:3
165:)
163:3
20:)
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