Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane
Efekti supstituenata i strukture na kinetiku reakcije N-(supstituisanih)-m- i -p-aminobenzoevih kiselina sa diazodifenilmetanom
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The rate constants for the reaction of twenty-two N-(substituted phenylmethylene)- m- and -p-aminobenzoic acids with diazodiphenylmethane were determined in absolute ethanol at 30 °C. The effects of substituents on the reactivity of the investigated compounds were interpreted by correlation of the rate constants with LFER equations. The results of quantum mechanical calculations of the molecular structure together with experimental results gave a better insight into the effects of structure on the transmission of electronic effects of the substituents. New σ constants for substituted benzylideneamino group were calculated.
Konstante brzina reakcija između dvadeset dve N-(supstituisane fenilmetilen)-m- i -p-aminobenzoeve kiseline i diazodifenilmetana određene su u apsolutnom etanolu na 30 °C. Efekti supstituenata na reaktivnost ispitivanih jedinjenja su interpretirani korelacijom reakcionih konstanti pomoću LFER jednačina. Rezultati kvantno-mehaničkih računanja molekulske strukture zajedno sa eksperimentalnim rezultatima omogućili su bolje razumevanje uticaja strukture na prenos elektronskih efekata supstituenata. Izračunate su nove σ konstante za supstituisane benzilidenamino grupe.
Кључне речи:
rate constants / substituent and structural effects / geometry optimizationИзвор:
Journal of the Serbian Chemical Society, 2007, 72, 12, 1191-1200Издавач:
- Serbian Chemical Society, Belgrade
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Jovanović, Bratislav Ž. AU - Marinković, Aleksandar AU - Vitnik, Željko AU - Juranić, Ivan PY - 2007 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1114 AB - The rate constants for the reaction of twenty-two N-(substituted phenylmethylene)- m- and -p-aminobenzoic acids with diazodiphenylmethane were determined in absolute ethanol at 30 °C. The effects of substituents on the reactivity of the investigated compounds were interpreted by correlation of the rate constants with LFER equations. The results of quantum mechanical calculations of the molecular structure together with experimental results gave a better insight into the effects of structure on the transmission of electronic effects of the substituents. New σ constants for substituted benzylideneamino group were calculated. AB - Konstante brzina reakcija između dvadeset dve N-(supstituisane fenilmetilen)-m- i -p-aminobenzoeve kiseline i diazodifenilmetana određene su u apsolutnom etanolu na 30 °C. Efekti supstituenata na reaktivnost ispitivanih jedinjenja su interpretirani korelacijom reakcionih konstanti pomoću LFER jednačina. Rezultati kvantno-mehaničkih računanja molekulske strukture zajedno sa eksperimentalnim rezultatima omogućili su bolje razumevanje uticaja strukture na prenos elektronskih efekata supstituenata. Izračunate su nove σ konstante za supstituisane benzilidenamino grupe. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane T1 - Efekti supstituenata i strukture na kinetiku reakcije N-(supstituisanih)-m- i -p-aminobenzoevih kiselina sa diazodifenilmetanom EP - 1200 IS - 12 SP - 1191 VL - 72 UR - https://hdl.handle.net/21.15107/rcub_technorep_1114 ER -
@article{ author = "Jovanović, Bratislav Ž. and Marinković, Aleksandar and Vitnik, Željko and Juranić, Ivan", year = "2007", abstract = "The rate constants for the reaction of twenty-two N-(substituted phenylmethylene)- m- and -p-aminobenzoic acids with diazodiphenylmethane were determined in absolute ethanol at 30 °C. The effects of substituents on the reactivity of the investigated compounds were interpreted by correlation of the rate constants with LFER equations. The results of quantum mechanical calculations of the molecular structure together with experimental results gave a better insight into the effects of structure on the transmission of electronic effects of the substituents. New σ constants for substituted benzylideneamino group were calculated., Konstante brzina reakcija između dvadeset dve N-(supstituisane fenilmetilen)-m- i -p-aminobenzoeve kiseline i diazodifenilmetana određene su u apsolutnom etanolu na 30 °C. Efekti supstituenata na reaktivnost ispitivanih jedinjenja su interpretirani korelacijom reakcionih konstanti pomoću LFER jednačina. Rezultati kvantno-mehaničkih računanja molekulske strukture zajedno sa eksperimentalnim rezultatima omogućili su bolje razumevanje uticaja strukture na prenos elektronskih efekata supstituenata. Izračunate su nove σ konstante za supstituisane benzilidenamino grupe.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane, Efekti supstituenata i strukture na kinetiku reakcije N-(supstituisanih)-m- i -p-aminobenzoevih kiselina sa diazodifenilmetanom", pages = "1200-1191", number = "12", volume = "72", url = "https://hdl.handle.net/21.15107/rcub_technorep_1114" }
Jovanović, B. Ž., Marinković, A., Vitnik, Ž.,& Juranić, I.. (2007). Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 72(12), 1191-1200. https://hdl.handle.net/21.15107/rcub_technorep_1114
Jovanović BŽ, Marinković A, Vitnik Ž, Juranić I. Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society. 2007;72(12):1191-1200. https://hdl.handle.net/21.15107/rcub_technorep_1114 .
Jovanović, Bratislav Ž., Marinković, Aleksandar, Vitnik, Željko, Juranić, Ivan, "Substituent and structural effects on the kinetics of the reaction of N-(substituted phenylmethylene)-m- and -p-aminobenzoic acids with diazodiphenylmethane" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1191-1200, https://hdl.handle.net/21.15107/rcub_technorep_1114 .