Reactions of Aryl Diazonium Salts and Arylazo Alkyl Ethers. IV. Substituent Effects on the Rates of Some Reactions of syn-Arylazo Ethyl Ethers in Ethanol

TJ Broxton

doi:10.1071/ch9791031

Reactions of Aryl Diazonium Salts and Arylazo Alkyl Ethers. IV. Substituent Effects on the Rates of Some Reactions of syn-Arylazo Ethyl Ethers in Ethanol

Australian Journal of Chemistry ◽

10.1071/ch9791031 ◽

1979 ◽

Vol 32 (5) ◽

pp. 1031 ◽

Cited By ~ 4

Author(s):

TJ Broxton

Keyword(s):

Substituent Effects ◽

Diazonium Salts ◽

Recombination Mechanism ◽

Alkyl Ethers

Substituent effects on the rates of ionization (kIS), decomposition (kD) and syn-anti interconversion (kp) for a number of syn-arylazo ethyl ethers have been measured. The rates of ionization and syn-anti interconversion correlate well with sigma while the rates of decomposition correlate with σ+. Substituent effects on the ionization of the syn-ethers are compared to those for ionization of the anti-ethers. Substituent effects on the rate of syn-anti interconversion support the proposed ionization-recombination mechanism.

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Reactions of aryl diazonium salts and arylazo alkyl ethers. III. Substituent effects in the ionization of anti-arylazo ethyl ethers in ethanol

Australian Journal of Chemistry ◽

10.1071/ch9781519 ◽

1978 ◽

Vol 31 (7) ◽

pp. 1519 ◽

Cited By ~ 4

Author(s):

TJ Broxton

Keyword(s):

Substituent Effects ◽

Parameter Analysis ◽

Diazonium Salts ◽

Resonance Effects ◽

Inductive Effects ◽

Alkyl Ethers

A dual substituent parameter analysis of substituent effects on the ionization of anti-arylazo ethyl ethers in ethanol shows that the reaction is affected primarily by inductive effects. The reaction is insensitive to resonance effects and an explanation for this behaviour is offered.

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ChemInform Abstract: REACTIONS OF ARYL DIAZONIUM SALTS AND ARYLAZO ALKYL ETHERS. IV. SUBSTITUENT EFFECTS ON THE RATES OF SOME REACTIONS OF SYN-ARYLAZO ETHYL ETHERS IN ETHANOL

Chemischer Informationsdienst ◽

10.1002/chin.197941138 ◽

1979 ◽

Vol 10 (41) ◽

Author(s):

T. J. BROXTON

Keyword(s):

Substituent Effects ◽

Diazonium Salts ◽

Alkyl Ethers

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Reactions of aryl diazonium salts and arylazo alkyl ethers. VI. A comparison of the available methods for the measurement of the rate of ionization of (Z)-arylazo alkyl ethers in alcoholic solvents

Australian Journal of Chemistry ◽

10.1071/ch9820319 ◽

1982 ◽

Vol 35 (2) ◽

pp. 319 ◽

Cited By ~ 2

Author(s):

TJ Broxton ◽

MJ Mcleish

Keyword(s):

Substituent Effects ◽

Ionization Rate ◽

New Method ◽

Diazonium Salts ◽

Advantages And Disadvantages ◽

Diazonium Ions ◽

Alkyl Ethers ◽

Trapping Agent ◽

Ionization Rates

Two previously reported methods for the determination of the ionization rate of (Z)-arylazo alkyl ethers by using x-naphtholate ions as a trapping agent are compared. A new method, which uses thiophenolate ions to trap the free diazonium ions formed in this ionization, is reported. This method is recommended in preference to the earlier methods because it includes a correction for the effect of the ionic strength of the solution on the rate of ionization. Rates measured by the thiophenolate method are consequently lower than those measured by either of the two previous methods. The advantages and disadvantages of the new method are discussed. The magnitude of salt effects and substituent effects on the ionization of (Z)- and (E)-arylazo alkyl ethers are compared.

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