769:
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838:
853:
67:
179:
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883:
507:
20:
1273:
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".
768:
810:
42:
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 (
1173:
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".
1240:
Klaus Köhler; Peter
Simmendinger; Wolfgang Roelle; Wilfried Scholz; Andreas Valet; Mario Slongo (2010). "Paints and Coatings, 4. Pigments, Extenders, and Additives".
369:
334:
307:
749:
140:
Relative rates of chemical reactions provide useful insights into the effects of the steric bulk of substituents. Under standard conditions, methyl bromide
852:
97:
is a consequence of steric effects. Steric hindrance is the slowing of chemical reactions due to steric bulk. It is usually manifested in
837:
132:
Because steric effects have profound impact on properties, the steric properties of substituents have been assessed by numerous methods.
1312:
168:
1129:
Tolman, Chadwick A. (1970-05-01). "Phosphorus ligand exchange equilibriums on zerovalent nickel. Dominant role for steric effects".
1156:
Stephan, Douglas W. "Frustrated Lewis pairs": a concept for new reactivity and catalysis. Org. Biomol. Chem. 2008, 6, 1535–1539.
755:
871:
1257:
1223:
1113:
1028:
171:
provide another measure of the bulk of substituents. A-values are derived from equilibrium measurements of monosubstituted
1355:
190:
above. It costs 1.74 kcal/mol for the methyl group to adopt to the axial position compared to the equatorial position.
1190:
1047:
997:
1326:
843:
717:. In organic chemistry, steric effects are nearly universal and affect the rates and activation energies of most
58:
result in structured groupings of molecules stabilized by the way that opposites attract and like charges repel.
786:
929:
1018:
105:. Steric hindrance is often exploited to control selectivity, such as slowing unwanted side-reactions.
1042:
E.L. Eliel, S.H. Wilen and L.N. Mander, Stereochemistry of
Organic Compounds, Wiley, New York (1994).
961:
Günther Maier; Stephan Pfriem; Ulrich Schäfer; Rudolf
Matusch (1978). "Tetra-tert-butyltetrahedrane".
529:
formed with the metal at the vertex and the hydrogen atoms at the perimeter of the cone (see figure).
1350:
935:
54:, which dictate the shape and reactivity of molecules. Steric repulsive forces between overlapping
43:
816:
905:
cation, difficult. It is difficult for electrophiles to get close enough to allow attack by the
78:
in the presence of a free secondary 3'-hydroxy group as a result of steric hindrance due to the
774:
759:
637:
522:
1172:
858:
801:
782:
724:
In biochemistry, steric effects are often exploited in naturally occurring molecules such as
175:. The extent that a substituent favors the equatorial position gives a measure of its bulk.
148:. The difference reflects the inhibition of attack on the compound with the sterically bulky
1239:
1206:
Pieter
Gijsman (2010). "Photostabilisation of Polymer Materials". In Norman S. Allen (ed.).
940:
924:
347:
312:
285:
187:
8:
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28:
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1245:
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1178:
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970:
919:
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341:
1334:
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309:) is a measure of the steric properties of the monomers that comprise a polymer.
79:
1215:
337:
55:
24:
1344:
1249:
1182:
428:
66:
736:
structure. In pharmacology, steric effects determine how and at what rate a
16:
Geometric aspects of ions and molecules affecting their shape and reactivity
1295:
974:
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714:
710:
178:
1014:
828:
824:
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172:
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149:
141:
121:
109:
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1108:(3rd ed.). New York: Oxford University Press. pp. 193–194.
906:
729:
706:
550:
534:
75:
1093:(fourth ed.). New York: John Wiley & Sons, Inc. p. 40.
1078:(first ed.). New York: John Wiley & Sons, Inc. p. 199.
1208:
Photochemistry and
Photophysics of Polymer Materials Photochemistry
902:
448:
388:
117:
113:
108:
Steric hindrance between adjacent groups can also affect torsional
87:
71:
1059:
Eliel, E.L.; Allinger, N.L.; Angyal, S.J.; G.A., Morrison (1965).
882:
733:
674:
468:
1020:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
344:
are equal. Sterically hindered monomers give polymers with low
725:
518:
183:
83:
934:
Reaction rate accelerate as result of steric hindrance in the
1327:
Steric: A Program to
Calculate the Steric Size of Molecules (
1012:
899:
891:
887:
1272:
112:. Steric hindrance is responsible for the observed shape of
506:
1089:
Romers, C.; Altona, C.; Buys, H.R.; Havinga, E. (1969).
831:-based products ranging from petrochemicals to plastics.
116:
and the low rates of racemization of 2,2'-disubstituted
1088:
1058:
820:
19:
877:
An isolable selenenic acid owing to steric protection.
101:, whereas discussion of steric effects often focus on
70:
Regioselective dimethoxytritylation of the primary 5'-
350:
315:
288:
1210:. Hoboken: John Wiley & Sons. pp. 627–679.
363:
328:
301:
50:of ions and molecules. Steric effects complement
1342:
700:
127:
990:Oligonucleotide synthesis: a practical approach
1242:Ullmann's Encyclopedia Of Industrial Chemistry
1205:
1175:Ullmann's Encyclopedia of Industrial Chemistry
1023:(6th ed.), New York: Wiley-Interscience,
740:will interact with its target bio-molecules.
1052:
1082:
909:of the nitrogen (nitrogen is shown in blue)
1177:. Weinheim: Wiley-VCH. pp. a19_313.
1122:
1036:
881:
505:
177:
65:
18:
1103:
744:Prominent sterically hindered compounds
274:
1343:
1128:
1073:
756:Tris(2,4-di-tert-butylphenyl)phosphite
1067:
336:is the temperature where the rate of
1063:. New York: Interscience Publishers.
987:
61:
13:
732:site may be buried within a large
371:'s, which are usually not useful.
186:group is 1.74 as derived from the
14:
1367:
1337: (archived December 22, 2017)
1306:
1106:Polymer Chemistry an Introduction
1104:Stevens, Malcolm P. (1999). "6".
898:reactions, like forming the tetra
870:
861:is a monomer, the corresponding
851:
844:Hindered amine light stabilizers
836:
809:
767:
748:
1266:
1233:
1199:
1166:
1150:
886:The steric effect of tri-(tert-
705:Steric effects are critical to
1097:
1006:
981:
954:
501:
1:
1323: (archived July 25, 2008)
947:
943:, also known as steric strain
701:Significance and applications
128:Measures of steric properties
930:Sterically induced reduction
846:are widely used in polymers.
517:are measures of the size of
135:
35:-butyl derivative is robust.
7:
913:
163:
103:intramolecular interactions
10:
1372:
1356:Physical organic chemistry
1216:10.1002/9780470594179.ch17
963:Angew. Chem. Int. Ed. Engl
1091:Topics in Stereochemistry
1076:Topics in Stereochemistry
1250:10.1002/14356007.o18_o03
1183:10.1002/14356007.a19_313
819:is used industrially as
800:, comprises the classic
525:. It is defined as the
380:Ceiling temperature (°C)
99:intermolecular reactions
1061:Conformational Analysis
817:2,6-Di-tert-butylphenol
988:Gait, Michael (1984).
975:10.1002/anie.197805201
910:
775:Tricyclohexylphosphine
533:Cone angles of common
523:coordination chemistry
511:
365:
330:
303:
191:
91:
36:
1074:Hirsch, J.A. (1967).
992:. Oxford: IRL Press.
885:
859:Titanium isopropoxide
802:frustrated Lewis pair
783:homogeneous catalysis
509:
366:
364:{\displaystyle T_{c}}
331:
329:{\displaystyle T_{c}}
304:
302:{\displaystyle T_{c}}
181:
69:
22:
1244:. pp. o18_o03.
941:Van der Waals strain
936:Thorpe–Ingold effect
925:Intramolecular force
721:to varying degrees.
348:
313:
286:
275:Ceiling temperatures
188:chemical equilibrium
144:10 faster than does
1144:10.1021/ja00713a007
1013:Smith, Michael B.;
538:
280:Ceiling temperature
911:
719:chemical reactions
532:
515:Ligand cone angles
512:
510:Ligand cone angle.
361:
326:
299:
192:
182:The A-value for a
92:
52:electronic effects
37:
1288:10.1021/ol016682s
1282:(22): 3569–3572.
1259:978-3-527-30673-2
1225:978-0-470-59417-9
1138:(10): 2956–2965.
1132:J. Am. Chem. Soc.
1115:978-0-19-512444-6
1030:978-0-471-72091-1
863:titanium ethoxide
698:
697:
499:
498:
272:
271:
146:neopentyl bromide
1363:
1315:chem.swin.edu.au
1313:Steric Effects (
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920:Collision theory
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823:stabilizers and
813:
779:phosphine ligand
771:
758:, a widely used
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342:depolymerization
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95:Steric hindrance
62:Steric hindrance
27:(R = H) readily
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1351:Stereochemistry
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1335:Wayback Machine
1321:Wayback Machine
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1276:Organic Letters
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80:dimethoxytrityl
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56:electron clouds
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40:Steric effects
25:cyclobutadiene
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429:1,3-butadiene
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1038:
1019:
1015:March, Jerry
1008:
989:
983:
969:(7): 520–1.
966:
962:
956:
825:antioxidants
762:in polymers.
728:, where the
723:
715:pharmacology
711:biochemistry
704:
659:
513:
278:
202:
197:
173:cyclohexanes
167:
139:
131:
107:
102:
98:
94:
93:
44:conformation
39:
38:
32:
31:but the R =
829:hydrocarbon
527:solid angle
502:Cone angles
460:=C(Me)CH=CH
409:isobutylene
198:Substituent
110:bond angles
86:ring (Py =
23:The parent
1345:Categories
948:References
785:and, with
777:, a bulky
760:stabilizer
545:Angle (°)
492:PhC(Me)=CH
383:Structure
142:solvolyzes
122:binaphthyl
48:reactivity
907:lone pair
730:catalytic
707:chemistry
638:P(cyclo-C
535:phosphine
136:Rate data
114:rotaxanes
76:thymidine
74:group of
29:dimerizes
1296:11678710
1017:(2007),
914:See also
903:ammonium
781:used in
673:P(2,4,6-
537:ligands
449:isoprene
440:=CHCH=CH
389:ethylene
169:A-values
164:A-values
118:biphenyl
88:pyridine
72:hydroxyl
1333:at the
1319:at the
734:protein
726:enzymes
519:ligands
476:PhCH=CH
469:styrene
377:Monomer
203:A-Value
160:group.
1294:
1256:
1222:
1189:
1112:
1046:
1027:
996:
894:makes
713:, and
542:Ligand
268:>4
184:methyl
84:ribose
46:) and
900:alkyl
892:amine
888:butyl
564:P(OCH
253:2.15
243:CH(CH
238:1.75
223:1.74
1292:PMID
1254:ISBN
1220:ISBN
1187:ISBN
1110:ISBN
1044:ISBN
1025:ISBN
994:ISBN
827:for
738:drug
694:212
668:182
662:-Bu)
653:179
632:145
611:132
597:P(CH
592:118
581:P(CH
575:107
420:=CMe
340:and
258:C(CH
120:and
33:tert
1284:doi
1246:doi
1212:doi
1179:doi
1158:doi
1140:doi
971:doi
787:B(C
617:P(C
558:87
521:in
473:395
453:466
433:585
413:175
400:=CH
393:610
150:(CH
1347::
1290:.
1278:.
1252:.
1218:.
1185:.
1136:92
967:17
965:.
821:UV
709:,
675:Me
658:P(
644:11
601:CH
551:PH
489:66
456:CH
436:CH
416:CH
396:CH
232:CH
228:CH
217:CH
212:0
90:).
1331:)
1317:)
1298:.
1286::
1280:3
1262:.
1248::
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1228:.
1214::
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1142::
1118:.
1002:.
977:.
973::
890:)
804:.
797:3
795:)
793:5
791:F
789:6
690:3
688:)
685:2
683:H
681:6
679:C
677:3
664:3
660:t
648:3
646:)
642:H
640:6
627:3
625:)
623:5
621:H
619:6
607:3
605:)
603:3
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587:3
585:)
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568:)
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494:2
478:2
462:2
458:2
442:2
438:2
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357:c
353:T
322:c
318:T
295:c
291:T
282:(
264:3
262:)
260:3
249:2
247:)
245:3
234:3
230:2
219:3
209:H
158:C
156:3
154:)
152:3
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