ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reactivity-structure correlations for anisole and eleven of its substituted derivatives established from bromination rate constants in liquid SO2, unlike observations in water, show the reaction to be highly sensitive to substituent effects, (ρH2O+ = -7.1; ρSO2+ = -10.51). This result is ascribed to the solvation of the methoxy group which decreases the conjugation of para-substituted (ρO+ = -9.70) compared to that of ortho-substituted derivatives (ρP+ = -8.86). The highly solvated transition state lies far from reactants on the reaction coordinate and the positive charge developed in this state is nearly unity.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660410