The gas-phase basicities (GB) of a series of ring-substituted phenylacetylenes were detd. Protonation occurs on the C≡C bond. A linear correlation exists between GB and the σ+ substituent parameters, which yields a ρ+ of -10.0. These results are compared with existing data for styrene derivs., which have consistently larger GB than their equally substituted PhC≡CH analogs and a very similar ρ+ of -10.7. These observations are briefly discussed also in terms of the protonation behavior of C:C and C≡C bonds in acidic aq. solns.
Gas-phase Basicity of Ring-substituted Phenylacetylenes / Franco, Marcuzzi; Giorgio, Modena; Cristina, Paradisi; C., Giancaspro; Speranza, Maurizio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 50:24(1985), pp. 4973-4975. [10.1021/jo00224a068]
Gas-phase Basicity of Ring-substituted Phenylacetylenes
SPERANZA, Maurizio
1985
Abstract
The gas-phase basicities (GB) of a series of ring-substituted phenylacetylenes were detd. Protonation occurs on the C≡C bond. A linear correlation exists between GB and the σ+ substituent parameters, which yields a ρ+ of -10.0. These results are compared with existing data for styrene derivs., which have consistently larger GB than their equally substituted PhC≡CH analogs and a very similar ρ+ of -10.7. These observations are briefly discussed also in terms of the protonation behavior of C:C and C≡C bonds in acidic aq. solns.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
