An Empirical Aromativcity Index (AIRT) Based on "Reversion to Type" in the Hydrolysis of Methyl Ethers, Methyl Thioethers, and Methyl Selenoethers Derived from Some Heterocyclic and Homocyclic Polyenes

DOI: 10.1016/S0040-4020(01)80460-9

Source and publish data:

Tetrahedron p. 7823 - 7838 (1992)

Update date:2022-07-30

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Authors:

Capon, Brian

Lew, Sing Quan

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Article abstract of DOI:10.1016/S0040-4020(01)80460-9

Hydronium ion catalysed hydrolysis and deuterium exchange in CD3CN-D2O (9:1 v/v) of the following compounds have been investigated: 1-methoxy-, 3-methoxy- and 1-methylthio-cyclohepta-1,3,5-triene, 1-methoxy-cyclooctatetraene, 2-methylthio-, 3-methylthio- and 2-methylseleno-benzofuran, 2-methylthio- and 3-methylthio-benzothiophene, and 2-methylthio-N-methyl-indole.The values of log k_ex/k_hyd for these compounds and those of a previous investigation have been used to define an aromaticity scale based on "reversion to type".

Full text of DOI:10.1016/S0040-4020(01)80460-9

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