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

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".