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Hydrolysis of Alkyl Halides Induced by Metal Ions: M⁺–S_N1 and M⁺–S_N2 Reactions

Elisei Sergeevich Rudakov ¹

Elisei Sergeevich Rudakov

Ivan Vasil'evich Kozhevnikov ¹

Ivan Vasil'evich Kozhevnikov

Valerii Vladimirovich Zamashchikov ¹

Valerii Vladimirovich Zamashchikov

¹ Institute of Physical-Organic Chemistry and Coal Chemistry, Academy of Sciences of the Ukrainian SSR, Donetsk

10.1070/RC1974v043n04ABEH001808

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Published 30 November 1973

Communication , Volume 43, Issue 4, 305-316

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1974, Volume 43, Issue 4

1 April 1974

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Rudakov E. S., Kozhevnikov I. V., Zamashchikov V. V. Hydrolysis of Alkyl Halides Induced by Metal Ions: M+–SN1 and M+–SN2 Reactions // Russian Chemical Reviews. 1974. Vol. 43. No. 4. pp. 305-316.

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Rudakov E. S., Kozhevnikov I. V., Zamashchikov V. V. Hydrolysis of Alkyl Halides Induced by Metal Ions: M+–SN1 and M+–SN2 Reactions // Russian Chemical Reviews. 1974. Vol. 43. No. 4. pp. 305-316.

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TY - JOUR

DO - 10.1070/RC1974v043n04ABEH001808

UR - https://rcr.colab.ws/publications/10.1070/RC1974v043n04ABEH001808

TI - Hydrolysis of Alkyl Halides Induced by Metal Ions: M+–SN1 and M+–SN2 Reactions

T2 - Russian Chemical Reviews

AU - Rudakov, Elisei Sergeevich

AU - Kozhevnikov, Ivan Vasil'evich

AU - Zamashchikov, Valerii Vladimirovich

PY - 1974

DA - 1973/11/30

PB - ANO Editorial Board of the journal Uspekhi Khimii

SP - 305-316

IS - 4

VL - 43

ER -

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@article{1974_Rudakov,

author = {Elisei Sergeevich Rudakov and Ivan Vasil'evich Kozhevnikov and Valerii Vladimirovich Zamashchikov},

title = {Hydrolysis of Alkyl Halides Induced by Metal Ions: M+–SN1 and M+–SN2 Reactions},

journal = {Russian Chemical Reviews},

year = {1974},

volume = {43},

publisher = {ANO Editorial Board of the journal Uspekhi Khimii},

month = {Nov},

url = {https://rcr.colab.ws/publications/10.1070/RC1974v043n04ABEH001808},

number = {4},

pages = {305--316},

doi = {10.1070/RC1974v043n04ABEH001808}

}

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Rudakov, Elisei Sergeevich, et al. “Hydrolysis of Alkyl Halides Induced by Metal Ions: M+–SN1 and M+–SN2 Reactions.” Russian Chemical Reviews, vol. 43, no. 4, Nov. 1974, pp. 305-316. https://rcr.colab.ws/publications/10.1070/RC1974v043n04ABEH001808.

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Abstract

Investigations of the kinetics, mechanism, and driving forces of hydrolyses of alkyl halides and several inorganic halides, induced by metal ions M⁺ in aqueous media, are summarised. Relations between the rate and the Lewis acidity of M⁺ are examined, together with models of M⁺–S_N1 and M⁺–S_N2 reactions.
A list of 163 references is included.

References

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1948

A. A. Krasnovskii

Zhur. Fiz. Khim. , 1956

M. F. Shostakovskii

"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952

10.1021/ja01285a030

The Mechanism of Substitution Reactions: the Reaction of Benzyl Chloride with Mercuric Salts¹

Roberts I., Hammett L.P.

Journal of the American Chemical Society , 1937

10.1515/zpch-1924-10814

Die katalytische Zersetzung des Nitramids und ihre physikalisch-chemische Bedeutung

Brönsted J.N., Pedersen K.

Zeitschrift fur Physikalische Chemie , 1924

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1953

10.1016/S0040-4039(01)96702-4

Brőnsted type correlation for tert. butyl halide solvolysis under the action of metal ions

Rudakov E.S., Kozhevnikov I.V.

Tetrahedron Letters , 1971

V. N. Kondrat'ev

"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959

V. H. Lynch

Carnegie Inst. Year Book , 1954

10.

T. A. Kryukova

"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959

11.

T. T. Bannister

Diss. Abstr. , 1959

12.

10.1007/BF00624365

A note on the rates of solvolysis of some alkyl chlorides

Anataraman R., Saramma K.

Die Naturwissenschaften , 1963

13.

10.1139/v65-233

ELECTROPHILIC CATALYSIS IN SOLVOLYTIC REACTIONS: VII. SOLVENT EFFECT

Anantaraman R., Saramma K.

Canadian Journal of Chemistry , 1965

14.

10.1139/v66-364

ELECTROPHILIC CATALYSIS IN SOLVOLYTIC REACTIONS: IX. INDUCTOMERIC EFFECT

Anantaraman R., Nair M.R.

Canadian Journal of Chemistry , 1966

15.

A. S. Holt

"Research in Photosynthesis" , 1957

16.

10.1021/ja00871a005

The Effects of Aqueous Electrolytes on the Activity Coefficient of t-Butyl Chloride and of its Solvolysis Transition State

Clarke G.A., Taft R.W.

Journal of the American Chemical Society , 1962

17.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1958

18.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1951

19.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1959

20.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1954

21.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1958

22.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1958

23.

N. V. Vostrilova

Dokl. Akad. Nauk Uzbek. SSR , 1958

24.

M. S. Ashkinazi

Dokl. Akad. Nauk SSSR , 1951

25.

G. W. Robinson

J. Chem. Phys. , 1955

26.

B. Ya. Dain

1957

27.

A. A. Krasnovskii

Biofizika , 1956

28.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1955

29.

10.3891/acta.chem.scand.21-0397

Kinetics of the Hydrolysis of Alkyl Halides in Perchloric Acid-Water Mixtures.

Koskikallio J., Williams D.R., Nilsson Å., Sandström J., Theorell H., Blinc R., Paušak S., Ehrenberg L., Dumanović J.

Acta Chemica Scandinavica , 1967

30.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1954

31.

10.1039/jr9600001972

401. Electrophilic catalysis in nucleophilic substitution and elimination. Part II. Kinetics and mechanisms of reaction of t-butyl chloride with pyridine, tribenzylamine, radio-chloride ions and hydrogen radio-chloride in nitromethane

Pocker Y.

Journal of the Chemical Society (Resumed) , 1960

32.

10.1021/ja00710a047

Electrostatic catalysis of ionic aggregates. I. Ionization and dissociation of trityl chloride and hydrogen chloride in lithium perchlorate-diethyl ether solutions

Pocker Y., Buchholz R.F.

Journal of the American Chemical Society , 1970

33.

10.1021/jo01278a028

Leaving group effects in solvolysis reactions

Buckson R.L., Smith S.G.

Journal of Organic Chemistry , 1967

34.

10.1021/ja01264a020

The Role of Neighboring Groups in Replacement Reactions. I. Retention of Configuration in the Reaction of Some Dihalides and Acetoxyhalides with Silver Acetate¹

Winstein S., Buckles R.E.

Journal of the American Chemical Society , 1942

35.

Z. K. Maizus

Dokl. Akad. Nauk SSSR , 1960

36.

J. Billon

Bull. Soc. chim. France , 1960

37.

L. M. Kosobutskaya

Dokl. Akad. Nauk SSSR , 1950

38.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1956

39.

V. F. Gachkovskii

Biofizika , 1959

40.

10.1021/j100849a019

Theoretical relations among rate constants, barriers, and Broensted slopes of chemical reactions

Marcus R.A.

The Journal of Physical Chemistry , 1968

41.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1950

42.

10.1021/ja01042a082

Broensted coefficients larger than 1 and less than 0 for proton removal from carbon acids

Bordwell F.G., Boyle W.J., Hautala J.A., Yee K.C.

Journal of the American Chemical Society , 1969

43.

10.1021/ja01054a003

Unusual slopes of free energy plots in kinetics

Marcus R.A.

Journal of the American Chemical Society , 1969

44.

10.1021/ja00713a062

Deviant Broensted relations

Kresge A.J.

Journal of the American Chemical Society , 1970

45.

10.1021/ja00731a018

Vinyl ether hydrolysis. III. Broensted relations and transition state structure

Kresge A.J., Chen H., Chiang Y., Murrill E., Payne M.A., Sagatys D.S.

Journal of the American Chemical Society , 1971

46.

10.1021/ja00731a034

Broensted coefficients and .rho. values as guides to transition-state structures in deprotonation reactions

Bordwell F.G., Boyle W.J.

Journal of the American Chemical Society , 1971

47.

10.1021/ja00723a019

Equilibrium and kinetic acidities of nitroalkanes and their relation to transition state structures

Bordwell F.G., Boyle W.J., Yee K.

Journal of the American Chemical Society , 1970

48.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1955

49.

10.1039/j19710001610

Substitution at saturated carbon. Part XII. Calculation of the electrostatic contribution to free energies of transfer from methanol to aqueous methanol and to water of solutes and transition states. A new method for the examination of transition states

Abraham M.H., Johnston G.F.

Journal of the Chemical Society A Inorganic Physical Theoretical , 1971

50.

G. Glacomello

Gazzetta. , 1935

51.

10.1021/ja00729a022

Mercuric chloride promoted reactions of p-chlorobenzhydryl chloride

Diaz A.F., Reich I.L., Winstein S.

Journal of the American Chemical Society , 1970

52.

10.1021/ja00759a055

Carbon to metal chlorine exchange. III. Mercuric chloride promoted reactions of exonorbornyl chloride

Hardy J.P., Ceccon A., Diaz A.F., Winstein S.

Journal of the American Chemical Society , 1972

53.

10.1021/ja00762a029

Carbon-to-metal chlorine exchange. IV. Mercuric salt promoted acetolysis of exo-norbornyl chloride

Hardy J.P., Diaz A.F., Winstein S.

Journal of the American Chemical Society , 1972

54.

10.1021/jo01278a058

Silver ion-assisted solvolysis of phenacyl halides in aqueous ethanol

Pasto D.J., Garves K.

Journal of Organic Chemistry , 1967

55.

10.1021/ja01579a005

Kinetics and Mechanism of the Reactions between Chloroaquochromium(III) Ions and Silver Ion

Elving P.J., Zemel B.

Journal of the American Chemical Society , 1957

56.

10.1021/ic50026a018

Aquation of Chloropentaaquochromium(III) Ion Catalyzed by Mercury(II) Complexes

Espenson J.H., Birk J.P.

Inorganic Chemistry , 1965

57.

R. Livingston

"Research in Photosynthesis" , 1957

58.

10.1021/ja00708a018

Induced solvolysis of halochromium(III) and azidochromium(III) ions and the spontaneous solvolysis of iodochromium(III) ion in water-methanol mixed solvents

Ferraris S.P., King E.L.

Journal of the American Chemical Society , 1970

59.

10.1021/ja01559a001

The Mechanisms of Substitution Reactions of Octahedral Complexes: The Induced Aquation of the Halogenopentamminecobaltic Ions by Metal Cations

Posey F.A., Taube H.

Journal of the American Chemical Society , 1957

60.

10.1021/ic50063a014

Rates of some mercury(II)-catalyzed aquations of chloroaminecobalt(III) complexes

Bifano C., Linck R.G.

Inorganic Chemistry , 1968

61.

10.1039/j19710000118

Kinetics of thallium(III)[and mercury(II)]-catalysed aquations of the chloropenta-amminecobalt(III) and cis- and trans-dichlorobis(ethylenediamine)cobalt(III) complexes

Foong S.W., Kipling B., Sykes A.G.

Journal of the Chemical Society A Inorganic Physical Theoretical , 1971

62.

10.1039/jr9630002788

517. Catalysis of the elimination of chloride ion from chloro(ethylenediaminetriacetatoacetate)cobaltate(III) and its conjugate acid by metal cations

Dyke R., Higginson W.C.

Journal of the Chemical Society (Resumed) , 1963

63.

1930

64.

10.1039/j19690001164

Catalysis by metal cations. Part II. A further study of the elimination of chloride ion from chloro(ethylenediaminetriacetatoacetate)cobaltate(III) catalysed by metal cations

Tanner S.P., Higginson W.C.

Journal of the Chemical Society A Inorganic Physical Theoretical , 1969

65.

10.1039/jr9640002375

447. The aquation of fluoropentamminecobalt(III) cation in neutral and in acidic solutions

Chan S.C.

Journal of the Chemical Society (Resumed) , 1964

66.

10.1021/ja01600a019

Mechanism of Substitution Reactions of Complex Ions. XI.¹ Rates of Hydrolysis and Racemization of Difluoro-bis-(ethylenediamine)-cobalt(III)^2,3

Basolo F., Matoush W.R., Pearson R.G.

Journal of the American Chemical Society , 1956

67.

10.1021/ja01467a004

Kinetics of Hydrolysis of cis-Difluoro-bis-(ethylenediamine)-chromium(III) Cation¹

Fehrmann K.R., Garner C.S.

Journal of the American Chemical Society , 1961

68.

10.1021/ic50026a019

The Rate of Aquation of Halopentaaquochromium(III) Ion in Acidic Aqueous Solution

Swaddle T.W., King E.L.

Inorganic Chemistry , 1965

69.

10.1021/ic50096a004

Substitution reactions of metallic complexes of .beta.,.beta.',.beta."-triaminotriethylamine. V. Kinetics acid hydrolysis of difluoro(triaminotriethylamine)cobalt(III)ion

Madan S.K., Kuo K.

Inorganic Chemistry , 1971

70.

10.1016/0022-1902(69)80024-2

The acid catalyzed hydrolysis of hexafluorophosphate

Gebala A.E., Jones M.M.

Journal of Inorganic and Nuclear Chemistry , 1969

71.

10.1038/197786a0

Influence of Polyvalent Cations on the Rate of Electro-reductio n and Aquation of Co(NH3)5Xn+ Complexes

VLČEK A.A.

Nature , 1963

72.

10.1021/ja00998a044

Catalysis and inhibition of the hydrolysis of xenon difluoride

Beck M.T., Dozsa L.

Journal of the American Chemical Society , 1967

73.

10.1021/ja00707a013

Ligand substitution catalysis via hard acid-hard base interaction

Clark H.R., Jones M.M.

Journal of the American Chemical Society , 1970

74.

10.1021/ic50042a010

Catalytic Hydrolysis of Hydroxopentafluoroarsenate(V) Ion in the Presence of Iron(III) Complexes

Johnson W.L., Jones M.M.

Inorganic Chemistry , 1966

75.

10.1021/ja01609a037

Model Reactions of Phosphorus-containing Enzyme Inactivators. IV.^1a The Catalytic Activity of Certain Metal Salts and Chelates in the Hydrolysis of Diisopropyl Fluorophosphate^1b

Wagner-Jauregg T., Hackley B.E., Lies T.A., Owens O.O., Proper R.

Journal of the American Chemical Society , 1955

76.

10.1021/ja01569a013

Metal Chelate Compounds as Catalysts in the Hydrolysis of Isopropyl Methylphosphonofluoridate and Diisopropylphosphorofluoridate¹

Courtney R.C., Gustafson R.L., Westerback S.J., Hyytiainen H., Chaberek S.C., Martell A.E.

Journal of the American Chemical Society , 1957

77.

10.1021/ja00871a007

A Kinetic Study of the Copper(II) Chelate-catalyzed Hydrolysis of Isopropyl Methylphosphonofluoridate (Sarin)

Gustafson R.L., Martell A.E.

Journal of the American Chemical Society , 1962

78.

A. A. Krasnovskii

Dokl. Akad. Nauk SSSR , 1949

79.

10.1016/0020-1650(72)80144-2

Brönsted type correlation for metal ion induced aquation of halogeno complexes. Role of charge of the complex

Kozhevnikov I.V., Rudakov E.S.

Inorganic and Nuclear Chemistry Letters , 1972

80.

10.1021/ic50095a014

Kinetics of the aquation of dichlorotetraaquochromium(III) catalyzed by monosubstituted mercury(II) complexes

Birk J.P.

Inorganic Chemistry , 1971

81.

10.1021/ic50086a008

Kinetics of the aquation of the isomeric dichlorotetraaquochromium(III) ions catalyzed by mercury(II) ion

Birk J.P.

Inorganic Chemistry , 1970

82.

10.1021/ic50038a041

Kinetics and Mechanism of the Reaction of Chloropentaamminechromium(III) Ion and Mercury(II)

Espenson J.H., Hubbard S.R.

Inorganic Chemistry , 1966

83.

10.1039/j19690000202

Octahedral cobalt(III) complexes of the chloropenta-ammine type. Part XV. The mercury(II)-catalysed aquation of some cis-chloro(amine)-bis(ethylenediamine)cobalt(III) cations in aqueous solution

Chan S.C., Chan S.F.

Journal of the Chemical Society A Inorganic Physical Theoretical , 1969

84.

10.1039/j19660000138

Octahedral cobalt(III) complexes of the chloropentammine type. Part IV. The hydrolyses of cis-chloroallylamine- and cis-chloropropargylamine-bis(ethylenediamine)cobalt(III) cations

Chan S.C., Leh F.

Journal of the Chemical Society A Inorganic Physical Theoretical , 1966

85.

10.1021/ic50103a052

Mercury(II)-catalyzed aquation of monochloroiron(III)

Carlyle D.W., Gibson D.

Inorganic Chemistry , 1971

86.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1958

87.

J. F. Arens

"Advances in Organic Chemistry" , 1960

88.

10.1021/ja01401a015

THE VELOCITY OF IONIC REACTIONS

Brönsted J.N., Livingston R.

Journal of the American Chemical Society , 1927

89.

A. A. Krasnovskii

Izd. Akad. Nauk SSSR, Moscow , 1955

90.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1951

91.

L. M. Vorob'eva

Biokhimiya , 1956

92.

10.1039/jr9610004637

907. The mechanism and steric course of octahedral aquation. Part IV. The aquation of cis- and trans-dichloro- and cis- and trans-chlorohydroxo-bis(ethylenediamine)cobalt(III) salts

Baldwin M.E., Chan S.C., Tobe M.L.

Journal of the Chemical Society (Resumed) , 1961

93.

V. B. Evstigneev

Dokl. Akad. Nauk SSSR , 1956

94.

10.1021/ja01018a017

The kinetics of the spontaneous and mercury(II)-catalyzed aquation and isomerization of the sulfur-bonded monothiocyanate complex of chromium(III)

Orhanovic M., Sutin N.

Journal of the American Chemical Society , 1968

95.

10.1021/ja01096a051

The Preparation and Isomerization of the Sulfur-Bonded Monothiocyanate Complex of Chromium(III)¹

Haim A., Sutin N.

Journal of the American Chemical Society , 1965

96.

10.1021/ic50037a037

The Mechanism of the Reaction of Carbonatopentaamminecobalt(III) witn Divalent Ions

Jordan R.B., Sargeson A.M., Taube H.

Inorganic Chemistry , 1966

97.

10.1039/jr9610004624

905. The concerted action of fluoride and silver ions on diethyl ethylphosphonothiolate in aqueous solution

Saville B.

Journal of the Chemical Society (Resumed) , 1961

98.

10.1039/jr9620004062

793. Solvolysis of unsaturated sulphides assisted by silver ion

Saville B.

Journal of the Chemical Society (Resumed) , 1962

99.

V. V. Zolotarev

1938

100.

10.1016/S0040-4039(01)88066-7

The kinetics and mechanism of metal ion promoted thiol ester hydrolysis

Satchell D.P., Secemski I.I.

Tetrahedron Letters , 1969

101.

10.1039/j29700001306

Acylation. Part XXXIV. The kinetics and mechanism of metal ion-promoted hydrolysis of S-esters, -acids, and -anhydrides in aqueous solution

Satchell D.P., Secemski I.I.

Journal of the Chemical Society B Physical Organic , 1970

102.

102

F. Fichter

Helv. Chim. Acta , 1922

103.

10.1515/zpch-1909-0118

Chemical dynamics of the alkyl iodides. Part II

Burke Κ.Α., Donnan F.G.

Zeitschrift fur Physikalische Chemie , 1909

104.

10.1039/CT9109700346

XXXIX.—Reactivity of the halogens in organic compounds. Part IV. Interaction of bromoacetic, α-bromopropionic, and α-bromobutyric acids and their sodium salts with silver salts in aqueous solution. Catalytic action of silver halides

Senter G.

Journal of the Chemical Society Transactions , 1910

105.

10.1039/CT9119900095

XI.—Reactivity of the halogens in organic compounds. Part V. Interaction of esters of the bromo-substituted fatty acids with silver nitrate in alcoholic solution

Senter G.

Journal of the Chemical Society Transactions , 1911

106.

10.1039/jr9370001236

255. Reaction kinetics and the Walden inversion. Part IV. Action of silver salts in hydroxylic solvents on β-n-octyl bromide and α-phenylethyl chloride

Hughes E.D., Ingold C.K., Masterman S.

Journal of the Chemical Society (Resumed) , 1937

107.

10.1039/jr9370001243

256. Reaction kinetics and the Walden inversion. Part V. Action of silver salts in hydroxylic solvents on α-bromopropionic acid, its methyl ester, and sodium salt

Cowdrey W.A., Hughes E.D., Ingold C.K.

Journal of the Chemical Society (Resumed) , 1937

108.

10.1039/jr9460000166

47. Mechanism of substitution at a saturated carbon atom. Part XXIX. The rôle of steric hindrance. (Section D) the mechanism of the reaction of neopentyl bromide with aqueous ethyl alcohol

Dostrovsky I., Hughes E.D.

Journal of the Chemical Society (Resumed) , 1946

109.

10.1039/jr9460000169

48. Mechanism of substitution at a saturated carbon atom. Part XXX. The rôle of steric hindrance. (Section E) a comparison of the rates of reaction of methyl, ethyl, n-propyl, isobutyl, and neopentyl halides with silver nitrate in aqueous ethyl alcohol

Dostrovsky I., Hughes E.D.

Journal of the Chemical Society (Resumed) , 1946

110.

10.1039/JR9460000173

50. Mechanism of substitution at a saturated carbon atom. Part XXXII. The rôle of steric hindrance. (Section G) magnitude of steric effects, range of occurrence of steric and polar effects, and place of the wagner rearrangement in nucleophilic substitution and elimination

Dostrovsky I., Hughes E.D., Ingold C.K.

Journal of the Chemical Society (Resumed) , 1946

111.

10.1021/ja01388a016

THE ALCOHOLYSIS AND HYDROLYSIS OF SOME ALKYL HALIDES IN NEUTRAL SOLUTION

Nicolet B.H., Stevens D.R.

Journal of the American Chemical Society , 1928

112.

10.1021/ja01388a031

THE REACTION OF ISOPROPYL IODIDE WITH MERCURIC CHLORIDE

Nicolet B.H., Potts W.M.

Journal of the American Chemical Society , 1928

113.

10.1021/ja01186a050

Electrophilic Attack on Halogen in a Homogeneous Medium: Reaction of Mercuric Nitrate with some Primary and Secondary Alkyl Bromides

Benfey O.T.

Journal of the American Chemical Society , 1948

114.

10.1021/ja01116a044

Relative Reactivities of Organic Halides in Displacement Reactions. II. Reaction of Mercuric Nitrate with Some Normal Chain Alkyl and Aralkyl Bromides¹

Oae S., Werf C.A.

Journal of the American Chemical Society , 1953

115.

10.1039/jr9600004940

958. Solvolysis and rearrangement of n-propyl bromide under the influence of mercury salts in slightly aqueous formic acid

Coe J.S., Gold V.

Journal of the Chemical Society (Resumed) , 1960

116.

10.1021/ja01628a064

The Mechanism of the Reaction of Silver Nitrite with Alkyl Halides. The Contrasting Reactions of Silver and Alkali Metal Salts with Alkyl Halides. The Alkylation of Ambident Anions1,2

Kornblum N., Smiley R.A., Blackwood R.K., Iffland D.C.

Journal of the American Chemical Society , 1955

117.

10.1021/ja01514a020

Reactions of Alkyl Halides with Silver Nitrate in Pyridine¹

Vona J.A., Steigman J.

Journal of the American Chemical Society , 1959

118.

10.1021/ja01488a051

Ion-Pair Formation in the Reactions of Alkyl Iodides with Silver Salts

Hammond G.S., Hawthorne M.F., Waters J.H., Graybill B.M.

Journal of the American Chemical Society , 1960

119.

119

V. V. Levchenko

Zhur. Obshch. Khim. , 1947

120.

10.1021/ja00949a018

Electrophilic Catalysis in Nucleophilic Substitution and Elimination. III. Conductances of Some Silver and Tetraethylammonium Salts in Acetonitrile and the Kinetics of Reaction of 2-Octyl Bromide with Tetraethylammonium and Silver Nitrates in That Solvent^1,2

Pocker Y., Kevill D.N.

Journal of the American Chemical Society , 1965

121.

10.1021/ja00949a019

Electrophilic Catalysis in Nucleophilic Substitution and Elimination. IV. Kinetics of Reaction of 2-Octyl Bromide with Tetraethylammonium and Silver Perchlorates and Nitrites in Acetonitrile^1,2

Pocker Y., Kevill D.N.

Journal of the American Chemical Society , 1965

122.

10.1021/ja00949a020

Electrophilic Catalysis in Nucleophilic Substitution and Elimination. V. Stereochemical Studies Involving Reactions of (+)-2-Octyl Bromide in Acetonitrile^1,2

Pocker Y., Kevill D.N.

Journal of the American Chemical Society , 1965

123.

10.1021/ja00950a015

Electrophilic Catalysis in Nucleophilic Substitution and Elimination. VI. The Reaction of Silver Perchlorate and of Silver Perchlorate-Tetra-n-butylammonium Perchlorate Mixtures with 2-Octyl Bromide in Benzene^1,2

Pocker Y., Kevill D.N.

Journal of the American Chemical Society , 1965

124.

124

V. V. Levchenko

Zhur. Obshch. Khim. , 1952

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.

10.1039/jr9640002542

488. The kinetics of the reaction of methyl iodide with silver nitrate and silver perchlorate in aqueous solution

Colcleugh D.W., Moelwyn-Hughes E.A.

Journal of the Chemical Society (Resumed) , 1964

133.

10.1002/9780470171837.ch5

Solvolysis in Water

Robertson R.E.

Progress in Physical Organic Chemistry , 1967

134.

10.1139/v66-094

EFFECT OF α-METHYLATION ON THE PARAMETERS CHARACTERIZING HYDROLYSIS IN WATER FOR A SERIES OF HALIDES AND SULFONATES

Heppolette R.L., Robertson R.E.

Canadian Journal of Chemistry , 1966

135.

135

V. V. Korshak

Dokl. Akad. Nauk SSSR , 1945

136.

136

V. V. Korshak

Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954

137.

10.1070/RC1970v039n10ABEH002047

Dual Reactivity of Ambident Anions

Shevelev S.A.

Russian Chemical Reviews , 1970

138.

10.1021/ja01080a026

Substitution at a Saturated Carbon Atom. IV. A Clarification of the Mechanism of Solvolyses of 2-Octyl Sulfonates. Stereochemical Considerations¹

Weiner H., Sneen R.A.

Journal of the American Chemical Society , 1965

139.

10.1021/ja01080a027

Substitution at a Saturated Carbon Atom. V. A Clarification of the Mechanism of Solvolyses of 2-Octyl Sulfonates. Kinetic Considerations¹

Weiner H., Sneen R.A.

Journal of the American Chemical Society , 1965

140.

10.1021/ja01030a026

Substitution at a saturated carbon atom. X. Unification of mechanisms Snl and Sn2

Sneen R.A., Larsen J.W.

Journal of the American Chemical Society , 1969

141.

10.1021/ja01050a016

Substitution at a saturated carbon atom. XII. Generality of the ion-pair mechanism of nucleophilic substitution

Sneen R.A., Larsen J.W.

Journal of the American Chemical Society , 1969

142.

10.1139/v70-643

Studies in solvolysis. Part II. Some comments on the ion-pair mechanism for displacements at a primary carbon atom

Scott J.M.

Canadian Journal of Chemistry , 1970

143.

10.1021/ja01043a055

Metal ion promoted hydrolysis of fluorocarbons

Clark H.R., Jones M.M.

Journal of the American Chemical Society , 1969

144.

10.1016/0021-9517(72)90131-5

The metal ion assisted hydrolysis of organic fluorides

CLARK H.

Journal of Catalysis , 1972

145.

10.1021/ja01183a075

Kinetic Evidence for a Termolecular Mechanism in Displacement Reactions of Triphenylmethyl Halides in Benzene Solution

Swain C.G.

Journal of the American Chemical Society , 1948

146.

10.1021/ja01150a113

Concerted Displacement Reactions. VI. m- and p-Substituent Effects as Evidence for a Unity of Mechanism in Organic Halide Reactions¹

Swain C.G., Langsdorf W.P.

Journal of the American Chemical Society , 1951

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.

10.1039/c19670000247

Evidence for an alkyl halide–silver ion complex in an S_NAg⁺reaction

Kevill D.N., Likhite V.V.

Chemical Communications (London) , 1967

153.

153

1899

154.

10.1016/S0040-4039(01)84483-X

Silver-ion assisted reactions of chloroformate esters in benzene

Kevill D.N., Reis W.A., Kevill J.B.

Tetrahedron Letters , 1972

155.

10.1021/j100886a504

The Role of Silver Nitrate Ion Pairs in the Alkyl Halide—Silver Nitrate Reaction

Parfitt G.D., Smith A.L., Walton A.G.

The Journal of Physical Chemistry , 1965

156.

10.1039/j29690000042

Heterogeneous catalysis in solution. Part IV. The effect of solids on some organic substitution reactions

Walton P.S., Spiro M.

Journal of the Chemical Society B Physical Organic , 1969

157.

10.1021/ja01156a072

The Argentation of Organic Iodides

Andrews L.J., Keefer R.M.

Journal of the American Chemical Society , 1951

158.

10.1021/ja01492a014

Catalyzed Hydrolysis of Benzyl Chloride

Koshy S., Anantaraman R.

Journal of the American Chemical Society , 1960

159.

159

J. Tafel

Z. Elektrochem. , 1911

160.

160

1912

161.

161

Friedl.

162.

10.1002/zaac.19603040505

Radiochemische Messung der L�slichkeit von Silberhalogeniden in Silbernitratl�sungen und die Komplexbildung der Silberhalogenide mit Silberionen

Lieser K.H.

Zeitschrift fur Anorganische und Allgemeine Chemie , 1960

163.

163

Friedl.

164.

164

1917

165.

10.1021/ja00732a026

Silver ion assisted solvolysis of .alpha.-bromoisobutyrophenone

Pasto D.J., Sevenair J.P.

Journal of the American Chemical Society , 1971

166.

166

1917