Nucleophilic substitution at sulfur. Kinetics of displacement reactions involving trithionate ion

R. Dale. Ritter; James H. Krueger

doi:10.1021/ja00711a020

Nucleophilic substitution at sulfur. Kinetics of displacement reactions involving trithionate ion

Journal of the American Chemical Society ◽

10.1021/ja00711a020 ◽

1970 ◽

Vol 92 (8) ◽

pp. 2316-2321 ◽

Cited By ~ 10

Author(s):

R. Dale. Ritter ◽

James H. Krueger

Keyword(s):

Nucleophilic Substitution ◽

Displacement Reactions ◽

Kinetics Of

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Aromatic Nucleophilic Substitution. XVIII. Kinetics of Reactions of 2-(Acetylamino)ethyl 2,6-Dinitrophenyl Ether andN-Acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline with Sodium Isopropoxide

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.56.2752 ◽

1983 ◽

Vol 56 (9) ◽

pp. 2752-2755

Author(s):

Shizen Sekiguchi ◽

Motohiko Hirai ◽

Noboru Tomoto

Keyword(s):

Nucleophilic Substitution ◽

Aromatic Nucleophilic Substitution ◽

Kinetics Of

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Kinetics of Displacement Reactions at the Sulfur Atom. I. Isotopic Exchange between Sulfite and Alkylthiosulfates

Journal of the American Chemical Society ◽

10.1021/ja01601a020 ◽

1956 ◽

Vol 78 (20) ◽

pp. 5203-5208 ◽

Cited By ~ 19

Author(s):

Antonino Fava ◽

Gastone Pajaro

Keyword(s):

Sulfur Atom ◽

Isotopic Exchange ◽

Displacement Reactions ◽

Kinetics Of

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ChemInform Abstract: BRIDGING THE GAP BETWEEN THE GAS PHASE AND SOLUTION: TRANSITION IN THE KINETICS OF NUCLEOPHILIC DISPLACEMENT REACTIONS

Chemischer Informationsdienst ◽

10.1002/chin.198122113 ◽

1981 ◽

Vol 12 (22) ◽

Author(s):

D. K. BOHME ◽

G. I. MACKAY

Keyword(s):

Gas Phase ◽

Nucleophilic Displacement ◽

Displacement Reactions ◽

Kinetics Of

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Electrophilic Displacement Reactions. III. Kinetics of the Reaction between Hydrogen Peroxide and Benzeneboronic Acid1

Journal of the American Chemical Society ◽

10.1021/ja01632a070 ◽

1954 ◽

Vol 76 (3) ◽

pp. 870-874 ◽

Cited By ~ 94

Author(s):

Henry G. Kuivila

Keyword(s):

Hydrogen Peroxide ◽

Displacement Reactions ◽

Kinetics Of

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Kinetics of nucleophilic substitution in 1,1-diaryl-2-fluoroethylenes

Journal of the Chemical Society B Physical Organic ◽

10.1039/j29690001100 ◽

1969 ◽

pp. 1100 ◽

Cited By ~ 3

Author(s):

P. Beltrame ◽

P. L. Beltrame ◽

M. L. Cereda ◽

G. Lazzerini

Keyword(s):

Nucleophilic Substitution ◽

Kinetics Of

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ChemInform Abstract: NUCLEOPHILIC SUBSTITUTION ON NITROGEN, KINETICS OF REACTIONS OF HYDROXYLAMINE-O-SULFONATE ION

Chemischer Informationsdienst ◽

10.1002/chin.197401285 ◽

1974 ◽

Vol 5 (1) ◽

Author(s):

J. H. KRUEGER ◽

P. F. BLANCHET ◽

A. P. LEE ◽

B. A. SUDBURY

Keyword(s):

Nucleophilic Substitution ◽

Kinetics Of

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Catalysis in aromatic nucleophilic substitution. Part 12.1 Kinetics of the reactions of some 2-phenoxy- and 2-( p-nitrophenoxy)-3-nitro-5-X-thiophenes with benzylamine and N-benzylmethylamine in benzene

Journal of the Chemical Society Perkin Transactions 2 ◽

10.1039/a705667b ◽

1998 ◽

pp. 325-334 ◽

Cited By ~ 7

Author(s):

Giovanni Consiglio ◽

Vincenzo Frenna ◽

Elisabetta Mezzina ◽

Antonio Pizzolato ◽

Domenico Spinelli

Keyword(s):

Nucleophilic Substitution ◽

Aromatic Nucleophilic Substitution ◽

Kinetics Of

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Ligand displacement reactions. Part III. Kinetics of the reactions between trimethyl phosphite and some tricarbonyl(arene)tungsten complexes

Journal of the Chemical Society A Inorganic Physical Theoretical ◽

10.1039/j19690001604 ◽

1969 ◽

pp. 1604 ◽

Cited By ~ 15

Author(s):

A. Pidcock ◽

J. D. Smith ◽

B. W. Taylor

Keyword(s):

Trimethyl Phosphite ◽

Tungsten Complexes ◽

Ligand Displacement ◽

Displacement Reactions ◽

Kinetics Of

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Additions and Corrections-Nucleophilic Substitution in Aromatic Ethers. I. Kinetics of the Methanolysis of 2,4-Dinitrodiphenyl Ethers

Journal of the American Chemical Society ◽

10.1021/ja01180a644 ◽

1949 ◽

Vol 71 (12) ◽

pp. 4169-4169

Author(s):

Yoshiro. Ogata ◽

Masaya. Okano

Keyword(s):

Nucleophilic Substitution ◽

Kinetics Of

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Kinetics of the chlorination of azobenzene and comparison with azoxybenzene

Australian Journal of Chemistry ◽

10.1071/ch9842249 ◽

1984 ◽

Vol 37 (11) ◽

pp. 2249

Author(s):

KA Ahmed ◽

PJ Hanhela ◽

M Hassan ◽

J Miller ◽

DB Paul

Keyword(s):

Nucleophilic Substitution ◽

Kinetic Data ◽

Electrophilic Substitution ◽

Relative Rate ◽

Molecular Chlorine ◽

Partial Rate ◽

Reaction Proceeds ◽

Kinetics Of ◽

No Activation

The activating effect of the phenylazo substituent in electrophilic substitution has been examined. The rates and partial rate factors for chlorination of azobenzene with molecular chlorine and protonated chlorine acetate have been determined relative to benzene. Whereas the chlorine acetate reaction proceeds readily (relative rate 4900) there is virtually no activation to chlorination by molecular chlorine. Complexes between azobenzene and bromine were, however, isolated and chatacterized. Their formation implies that during molecular halogenation reactions the electrophile is essentially unavailable. The relative chlorination rates for azobenzene and azoxybenzene have also been established: the phenylazo group is more activating towards protonated chlorine acetate whereas azoxybenzene (which does not complex with halogens) is the more reactive with molecular chlorine. The chlorination results confirm the versatility of the phenylazo group which is the first substituent for which kinetic data have been obtained quantifying activation of aromatic electrophilic, radical and nucleophilic substitution.

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