Reactivity of beta-aroylacrylic acids with diazodiphenylmethane
Апстракт
The rate constants for 10 trans-substituted beta-aroylacrylic acids in their reaction with diazodiphenylmethane (DDM) were determined in ethanol at 30 degrees C. The intention was to study the transmission of electronic effects of substituents on the phenyl nuclei to the carboxylic group reaction center, through the -C(=O)-CH=CH-group. The obtained rate constants were analyzed with the classical Hammett equation and the extended Hammett and Taft equation. It was possible, using Taft's relationship, to effect the separation of the overall polar effect into inductive and resonance components. The pattern of transmission through the observed conjugated system has been discussed. Conformational variations caused by variable substituents in an aromatic ring were calculated using the MNDO-AM I semiempirical method. The inclusion of a calculated conformational effect considerably improves the regression.
Кључне речи:
beta-aroylacrylic acids / diazodiphenylmethane / Hammett equationИзвор:
Journal of the Serbian Chemical Society, 1998, 63, 5, 359-365Издавач:
- Serbian Chemical Society, Belgrade
Напомена:
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Stevović, Ljubomir S. AU - Drakulić, Branko AU - Juranić, Ivan AU - Drmanić, Saša AU - Jovanović, Bratislav Ž. PY - 1998 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/157 AB - The rate constants for 10 trans-substituted beta-aroylacrylic acids in their reaction with diazodiphenylmethane (DDM) were determined in ethanol at 30 degrees C. The intention was to study the transmission of electronic effects of substituents on the phenyl nuclei to the carboxylic group reaction center, through the -C(=O)-CH=CH-group. The obtained rate constants were analyzed with the classical Hammett equation and the extended Hammett and Taft equation. It was possible, using Taft's relationship, to effect the separation of the overall polar effect into inductive and resonance components. The pattern of transmission through the observed conjugated system has been discussed. Conformational variations caused by variable substituents in an aromatic ring were calculated using the MNDO-AM I semiempirical method. The inclusion of a calculated conformational effect considerably improves the regression. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Reactivity of beta-aroylacrylic acids with diazodiphenylmethane EP - 365 IS - 5 SP - 359 VL - 63 UR - https://hdl.handle.net/21.15107/rcub_technorep_157 ER -
@article{ author = "Stevović, Ljubomir S. and Drakulić, Branko and Juranić, Ivan and Drmanić, Saša and Jovanović, Bratislav Ž.", year = "1998", abstract = "The rate constants for 10 trans-substituted beta-aroylacrylic acids in their reaction with diazodiphenylmethane (DDM) were determined in ethanol at 30 degrees C. The intention was to study the transmission of electronic effects of substituents on the phenyl nuclei to the carboxylic group reaction center, through the -C(=O)-CH=CH-group. The obtained rate constants were analyzed with the classical Hammett equation and the extended Hammett and Taft equation. It was possible, using Taft's relationship, to effect the separation of the overall polar effect into inductive and resonance components. The pattern of transmission through the observed conjugated system has been discussed. Conformational variations caused by variable substituents in an aromatic ring were calculated using the MNDO-AM I semiempirical method. The inclusion of a calculated conformational effect considerably improves the regression.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane", pages = "365-359", number = "5", volume = "63", url = "https://hdl.handle.net/21.15107/rcub_technorep_157" }
Stevović, L. S., Drakulić, B., Juranić, I., Drmanić, S.,& Jovanović, B. Ž.. (1998). Reactivity of beta-aroylacrylic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 63(5), 359-365. https://hdl.handle.net/21.15107/rcub_technorep_157
Stevović LS, Drakulić B, Juranić I, Drmanić S, Jovanović BŽ. Reactivity of beta-aroylacrylic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society. 1998;63(5):359-365. https://hdl.handle.net/21.15107/rcub_technorep_157 .
Stevović, Ljubomir S., Drakulić, Branko, Juranić, Ivan, Drmanić, Saša, Jovanović, Bratislav Ž., "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane" in Journal of the Serbian Chemical Society, 63, no. 5 (1998):359-365, https://hdl.handle.net/21.15107/rcub_technorep_157 .