Home / Articles / Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds

Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds

Vladimir Ivanovich Galkin 1
Vladimir Ivanovich Galkin
, 
Rustem Damirovich Sayakhov 1
Rustem Damirovich Sayakhov
, 
Rafael Askhatovich Cherkasov 1
Rafael Askhatovich Cherkasov
1 Kazan State University
10.1070/RC1991v060n08ABEH001113
Published 30 November 1990
Communication , Volume 60, Issue 8, 815-829
30
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Galkin V. I., Sayakhov R. D., Cherkasov R. A. Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds // Russian Chemical Reviews. 1991. Vol. 60. No. 8. pp. 815-829.
GOST all authors (up to 50)
Copy cite
Galkin V. I., Sayakhov R. D., Cherkasov R. A. Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds // Russian Chemical Reviews. 1991. Vol. 60. No. 8. pp. 815-829.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1991v060n08ABEH001113
UR - https://rcr.colab.ws/publications/10.1070/RC1991v060n08ABEH001113
TI - Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds
T2 - Russian Chemical Reviews
AU - Galkin, Vladimir Ivanovich
AU - Sayakhov, Rustem Damirovich
AU - Cherkasov, Rafael Askhatovich
PY - 1991
DA - 1990/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 815-829
IS - 8
VL - 60
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1991_Galkin,
author = {Vladimir Ivanovich Galkin and Rustem Damirovich Sayakhov and Rafael Askhatovich Cherkasov},
title = {Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds},
journal = {Russian Chemical Reviews},
year = {1991},
volume = {60},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1991v060n08ABEH001113},
number = {8},
pages = {815--829},
doi = {10.1070/RC1991v060n08ABEH001113}
}
MLA
Cite this
MLA
Copy cite
Galkin, Vladimir Ivanovich, et al. “Steric effects: the problem of their quantitative assessment and manifestation in the reactivity of organoelement compounds.” Russian Chemical Reviews, vol. 60, no. 8, Nov. 1991, pp. 815-829. https://rcr.colab.ws/publications/10.1070/RC1991v060n08ABEH001113.
Views / Visits / Downloads
17 / 17 / 3

Abstract

Literature data on the methods of quantitatively assessing steric effects and their manifestation in the reactivity of various organoelement compounds is systematised. The authors' own results are considered in the light of a model of frontal steric effects and of a calculated scale of steric constants RS, the high effectiveness of which has been demonstrated in more than 100 reaction series involving organic and organoelement compounds. The bibliography contains 202 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Treatment of Steric Effects
Gallo R.
Progress in Physical Organic Chemistry , 1983
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
Progress in the Theory of Acids and Bases
Kabachnik M.I.
Russian Chemical Reviews , 1979
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
26.
26
B. Ya. Dain
1957
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
33.
Calculation of steric effects in reactions
DeTar D.F.
Journal of the American Chemical Society , 1974
34.
Quantitative predictions of steric acceleration
DeTar D.F.
Journal of the American Chemical Society , 1974
35.
Theoretical calculation of steric effects in ester hydrolysis
DeTar D.F., Tenpas C.J.
Journal of the American Chemical Society , 1976
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
39
V. F. Gachkovskii
Biofizika , 1959
40.
40
A. A. Krasnovskii
Biofizika , 1960
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
42.
Theoretische Behandlung des Einflusses sterischer Effekte auf die Reaktivität aliphatischer Verbindungen I
Becker F.
Zeitschrift fur Naturforschung - Section A Journal of Physical Sciences , 1959
43.
Myricetin - ein charakteristisches Flavonol der Hamamelidaceae und Anacardiaceae
Reznik H., Egger K.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1960
44.
Theoretische Behandlung des Einflusses sterischer Effekte auf die Reaktivität aliphatischer Verbindungen
Becker F.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1961
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
The (p→d)π-bond in trisilylamine
Perkins P.G.
Chemical Communications (London) , 1967
48.
Ground states of molecules. 59. MNDO study of SN2 reactions and related processes
Carrion F., Dewar M.J.
Journal of the American Chemical Society , 1984
51.
Charge-density analysis of rotational barriers
Allen L.C., Jorgensen W.L.
Journal of the American Chemical Society , 1971
52.
Semiempirical calculation of barriers to pyramidal inversion for first- and second-row elements
Rauk A., Andose J.D., Frick W.G., Tang R., Mislow K.
Journal of the American Chemical Society , 1971
54.
Theoretical study of substituent effects. Analysis of steric repulsion by means of paired interacting orbitals
Fujimoto H., Mizutani Y., Endo J., Jinbu Y.
Journal of Organic Chemistry , 1989
55.
Topological Indices in Organic Chemistry
Stankevich M.I., Stankevich I.V., Zefirov N.S.
Russian Chemical Reviews , 1988
56.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
57.
Topological Indices
Balaban A.T., Chiriac A., Motoc I., Simon Z.
Overlap Determinant Method in the Theory of Pericyclic Reactions , 1980
58.
58
N. E. Khomutov
1953
59.
Kinetic Steric Factors and Connectivity Indices
Schug J.C., Viersx J.W., Seeman J.I.
Journal of Pharmaceutical Sciences , 1984
60.
60
A. N. Terenin
Optika i Spektrosk. , 1956
61.
On the Effects of Intramolecular van der Waals Forces
Bartell L.S.
Journal of Chemical Physics , 1960
65.
The nature of seat-ligand fitting in coordination space. Part 1. An introduction of ‘coordination seat’
Xing-Fu L., Tian-Gi S., Ao-Ling G., Guang-Li S., Peng-Nian S.
Inorganica Chimica Acta , 1987
69.
Steric effects in metal cluster compounds
Mingos D.M.
Inorganic Chemistry , 1982
70.
70
N. Bubnov
Biofizika , 1960
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
75.
Some peculiarities of structure, stability and reactivity of compounds containing metal—metal bonds
Titova S.N., Bychkov V.T., Domrachev G.A., Razuvaev G.A., Zakharov L.N., Alexandrov G.G., Struchkov Y.T.
Inorganica Chimica Acta , 1981
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
Intermolecular interaction of bis(alkylcyclopentadienyl)tungsten dihalogenides with tetracyanoethylene and tetracyanoquinodimethane studied by UV absorption spectroscopy
Tumanov A.A., Zakharov L.N., Sennikov P.G., Egorochkin A.N., Razuvaev G.A., Smirnov A.S., Dodonov V.A.
Journal of Organometallic Chemistry , 1984
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
A new method for evaluating the steric hindrance by substituent
Komatsuzaki T., Sakakibara K., Hirota M.
Tetrahedron Letters , 1989
83.
Steric effects on the formation of alkyl radicals and alkyl carbenium ions
Charton M.
Journal of the Chemical Society Perkin Transactions 2 , 1983
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
Some Observations Concerning Steric Factors
Newman M.S.
Journal of the American Chemical Society , 1950
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
Linear Steric Energy Relationships
Taft R.W.
Journal of the American Chemical Society , 1953
91.
Quantitative Separation of Hyperconjugation Effects from Steric Substituent Constants
Hancock C.K., Meyers E.A., Yager B.J.
Journal of the American Chemical Society , 1961
93.
The Change in the Six Number as a Variable in Quantitative Structure-Reactivity Correlations of Esters
Hancock C.K., Yager B.J., Falls C.P., Schreck J.O.
Journal of the American Chemical Society , 1963
95.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
96
L. M. Vorob'eva
Biokhimiya , 1958
97.
Effects of alkyl groups on rates of SN2 reactions
DeTar D.F.
Journal of Organic Chemistry , 1980
101.
Steric effects-II
Panaye A., MacPhee J.A., Dubois J.
Tetrahedron , 1980
103.
Steric effects. I. Esterification and acid-catalyzed hydrolysis of esters
Charton M.
Journal of the American Chemical Society , 1975
104.
Steric effects. II. Base-catalyzed ester hydrolysis
Charton M.
Journal of the American Chemical Society , 1975
105.
Steric effects. III. Bimolecular nucleophilic substitution
Charton M.
Journal of the American Chemical Society , 1975
106.
Steric effects. 7. Additional V constants
Charton M.
Journal of Organic Chemistry , 1976
107.
Steric effects. 12. Substituents at phosphorus
Charton M., Charton B.I.
Journal of Organic Chemistry , 1978
109.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
113.
Effects of alkyl groups on rates of acyl-transfer reactions
DeTar D.F.
Journal of Organic Chemistry , 1980
114.
Quantitative Models of Steric Effects
Unger S.H., Hansch C.
Progress in Physical Organic Chemistry , 1976
115.
Steric effects on conformationally mobile systems. The iodomethylation of 1-methyl-2-arylpyrrolidines related to nicotine
Seeman J.I., Secor H.V., Hartung H., Galzerano R.
Journal of the American Chemical Society , 1980
116.
Steric and conformational effects in nicotine chemistry
Seeman J.I., Secor H.V., Chavdarian C.G., Sanders E.B., Bassfield R.L., Whidby J.F.
Journal of Organic Chemistry , 1981
117.
The Analysis of the Ortho Effect
Fujita T., Nishioka T.
Progress in Physical Organic Chemistry , 1976
119.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
120.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
Nature of the ortho effect. II. Composition of the Taft steric parameters
Charton M.
Journal of the American Chemical Society , 1969
124.
Hyperconjugation as a parameter in correlation analysis
Charton M., Charton B.I.
Journal of Organic Chemistry , 1982
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
129.
129
J. Wiemann
Bull. Soc. chim. France , 1955
130.
130
J. Wiemann
Bull. Soc. chim. France , 1958
131.
131
N. Thooi
Compt. rend. , 1958
132.
STRUCTURE AND PROPERTIES OF ORGANOPHOSPHORUS COMPOUNDS
Kodolov V.I., Spasskii S.S.
Russian Chemical Reviews , 1964
133.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
134.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
135.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
136.
Strain effects on amine basicities
Alder R.W.
Chemical Reviews , 1989
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
139
I. L. Knunyants
1959
140.
140
1912
141.
141
Friedl.
142.
142
1913
143.
143
Friedl.
144.
144
1912
145.
145
Friedl.
146.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
147.
147
Y. Sasada
Acta Cryst. , 1898
148.
148
P. Kresse
Chem. Abs. , 1960
149.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
153
1899
154.
154
Friedl.
155.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
156.
A kinetic study of the chlorination of tertiary alcoholamines in alkaline media
Antelo J.M., Arce F., Armesto J.L., Garcia-Verdugo A., Penedo F.J., Varela A.
International Journal of Chemical Kinetics , 1985
157.
157
1903
158.
158
Friedl.
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
161.
161
Friedl.
163.
163
Friedl.
164.
Preparation of silylalkanethiols
Gornowicz G.A., Ryan J.W., Speier J.L.
Journal of Organic Chemistry , 1968
165.
Zur synthese von siloxanen
Scheim U., Grosse-Ruyken H., Rühlmann K., Porzel A.
Journal of Organometallic Chemistry , 1985
166.
The Acid Dissociation Constants of Aromatic Phosphonic Acids. I. Meta and Para Substituted Compounds1
Jaffé H.H., Freedman L.D., Doak G.O.
Journal of the American Chemical Society , 1953
167.
The Acid Dissociation Constants of Aromatic Phosphonic Acids. II. Compounds with Ortho Substituents
Jaffé H.H., Freedman L.D., Doak G.O.
Journal of the American Chemical Society , 1954
168.
168
1918
169.
169
Friedl.
170.
170
1918
171.
171
Friedl.
172.
172
1918
173.
Electronic effects of alkyl groups
Bordwell F.G., Fried H.E.
Tetrahedron Letters , 1977
174.
174
S. Calvert
India Rubber Tire Rev. , 1926
175.
175
I. Mayer
1966
176.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
177.
177
J. Henry
Proc. R. Irish Acad. , 1945
178.
178
1946
179.
179
Chem. Abs. , 1947
180.
180
1946
181.
181
Chem. Abs. , 1947
182.
182
1947
183.
183
Chem. Abs. , 1947
184.
184
F. Haurowitz
"The Chemistry and Function of Proteins" , 1965
185.
185
1954
186.
186
Chem. Abs. , 1956
187.
187
1954
188.
188
Chem. Abs. , 1955
189.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
190.
190
H. Law
J. Chem. Soc. , 1912
191.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
192.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
193.
193
E. Pannain
Gazzetta , 1909
194.
Mechanism of the oxidation of alkyl aryl and diphenyl sulfides by chromium(VI)
Srinivasan C., Chellamani A., Rajagopal S.
Journal of Organic Chemistry , 1985
195.
195
M. Allen
J. Chem. Soc. , 1961
197.
197
J. Sicher
Chem. Listy , 1955
198.
198
W. Cohen
Rec. Trav. chim. , 1919
199.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
200.
200
Ref. Zh. Khim. , 1975
201.
201
A. Aladjem
1969
202.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
203.
203
L. Andrieux
Compt. rend. , 1929
204.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
205.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
206.
206
J. Petersen
Z. Phys. Chem. , 1900
207.
207
F. Fichter
"Organische Elektrochemie" , 1942
208.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
209.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
210.
210
H. L. Wheeler
Chem. Zentr. , 1908
211.
211
C. Schall
Z. Elektrochem. , 1923
212.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
213.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) , 1966
214.
214
L. V. Pavlova
1965
215.
215
N. D. Tomashov
Zh. Prikl. Khim. , 1970
216.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
217.
217
1925
218.
218
Chem. Zentr. II , 1925
219.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955