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• W2335342405 startingPage "13079" @default.
• W2335342405 abstract "There are still some secrets left to this well-studied reaction. Previously unreported relationships discovered are as follows. The ordering of reactivities of C6H5X is the same as that of enthalpies of hydrogenation of the ring to the correspondingly substituted cyclohexane. The orientation of substitution (meta or ortho/para) is controlled by the dipole direction of the ipso-C-X bond, like an ON/OFF switch. The difference between the halogens and other deactivating groups is that the bond between the atom bonded to the ipso carbon has the positive end of the dipole on the ipso carbon for the halogens (C(δ+)-X(δ-)) but in the opposite direction (C(δ-)-X(δ+)) for other deactivating groups. This reverses the directing effect. For all X, including the halogens, ipso-C(δ+)-X(δ-) results in ortho/para substitution. p-(13)C NMR shifts of C6H5X greater than that of benzene predict meta substitution. A linear relationship exists between p-(13)C NMR shift and ΔHhyd, except for X = halogen. With halobenzenes, the ortho/para ratios of the products are linearly related to the ipso/ortho ratios of the (13)C shifts of C6H5X for chlorinations, brominations, nitrations, and protonations. The relative reactivities of the halobenzenes are linearly related to the p-(13)C NMR shifts. The electronegativities of X are linearly related to the (13)C NMR shifts of the ipso carbon." @default.
• W2335342405 created "2016-06-24" @default.
• W2335342405 creator A5034512665 @default.
• W2335342405 creator A5048429753 @default.
• W2335342405 creator A5086635894 @default.
• W2335342405 date "2013-12-03" @default.
• W2335342405 modified "2023-09-27" @default.
• W2335342405 title "Electrophilic Aromatic Substitution: Enthalpies of Hydrogenation of the Ring Determine Reactivities of C₆H₅X. The Direction of the C₆H₅–X Bond Dipole Determines Orientation of the Substitution" @default.
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• W2335342405 doi "https://doi.org/10.1021/jp409623j" @default.
• W2335342405 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24299174" @default.
• W2335342405 hasPublicationYear "2013" @default.
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