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Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study

Samo za registrovane korisnike
2013
Autori
Cvijetić, Ilija
Vitorović-Todorović, Maja D.
Juranić, Ivan
Drakulić, Branko
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the propos...ed reaction mechanism, which includes a highly ordered transition state.

Ključne reči:
Thia-Michael addition / Aroylacrylic acid phenylamides / Kinetics / Quantum chemical calculations / NMR spectroscopy
Izvor:
Monatshefte Fur Chemie, 2013, 144, 12, 1815-1824
Izdavač:
  • Springer Wien, Wien
Projekti:
  • Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-172035)
  • High-Performance Computing Infrastructure for South East Europe's Research Communities (EU-261499)

DOI: 10.1007/s00706-013-1084-6

ISSN: 0026-9247

WoS: 000327083100009

Scopus: 2-s2.0-84961983959
[ Google Scholar ]
2
2
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2689
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija
IHTM
TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan
AU  - Drakulić, Branko
PY  - 2013
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/2689
AB  - The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study
VL  - 144
IS  - 12
SP  - 1815
EP  - 1824
DO  - 10.1007/s00706-013-1084-6
ER  - 
@article{
author = "Cvijetić, Ilija and Vitorović-Todorović, Maja D. and Juranić, Ivan and Drakulić, Branko",
year = "2013",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2689",
abstract = "The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study",
volume = "144",
number = "12",
pages = "1815-1824",
doi = "10.1007/s00706-013-1084-6"
}
Cvijetić I, Vitorović-Todorović MD, Juranić I, Drakulić B. Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study. Monatshefte Fur Chemie. 2013;144(12):1815-1824
Cvijetić, I., Vitorović-Todorović, M. D., Juranić, I.,& Drakulić, B. (2013). Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study.
Monatshefte Fur ChemieSpringer Wien, Wien., 144(12), 1815-1824.
https://doi.org/10.1007/s00706-013-1084-6
Cvijetić Ilija, Vitorović-Todorović Maja D., Juranić Ivan, Drakulić Branko, "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study" 144, no. 12 (2013):1815-1824,
https://doi.org/10.1007/s00706-013-1084-6 .

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