MECHANISM OF BENZIDINE AND SEMIDINE REARRANGEMENTS. PART X. SUBSTRATE- ISOTOPE EFFECTS ON KINETICS AND PRODUCTS OF ACID REARRANGEMENT OF THE HYDRAZOBENZENES
Hydrazobenzene, its 4,4'-dideutero-derivatives, and a derivative C - deuterated everywhere except in 4,4'-positions, were rearranged with acid in aqueous dioxan and in aqueous and anhydrous ethanol; and comparisons were made of the rearrangement rates and product proportions. The products are benzidine 76 to 72%, and diphenyline 24 to 28%, the small variation depending on the solvent. Neither in para- nor in ortho-positions does deuteration make a detectable difference either to reaction rates or to product ratios. The aromatic proton losses are concluded to occur after the activation barrier for rearrangement has been surmounted, and after the mechanism has decisively branched towards the individual products. (auth)
- Research Organization:
- University Coll., London
- NSA Number:
- NSA-16-032990
- OSTI ID:
- 4777924
- Journal Information:
- Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc., Journal Name: Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc.; ISSN JCSOA
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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