TY  - JOUR
AU  - Assaleh, Fathi H.
AU  - Marinković, Aleksandar
AU  - Nikolić, Jasmina
AU  - Drmanić, Saša
AU  - Brković, Danijela V
AU  - Prlainović, Nevena
AU  - Jovanović, Bratislav Ž.
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3265
AB  - Linear free energy relationships (LFER) were applied to the kinetic data for the reaction of 5-substituted orotic acids, series 1, with diazodiphenylmethane (DDM) in N,N-dimethylformamide and compared with results obtained for 2-substituted benzoic acids, series 2. The correlation analysis of the kinetic data with sigma substituent parameters was carried out using SSP (single substituent parameter) methods. From the sign and value of proportinality constant rho, lower sensitivity to the substituent effect was obtained in series 1, 0.876, than in the series 2, 1.877. Evaluation of substituent "ortho-effect" was performed using the Charton model, which includes the steric substituent parameter, and Fujita and Nishioka's model, which describes the total ortho-effect as contribution of ordinary polar effect, the ortho-steric and ortho-polar effects. Results of correlations, obtained by using the Charton model, showed highest contribution of the polar effect, 0.861 vs. 2.101, whereas the steric effect is of lowest significance, 0.117 vs. 0.055, for series 1 and 2, respectively. Also, a low negative value of coefficient with the steric effect, -0.08, obtained from the Fujita-Nishioka model indicated low steric effect, influencing a decrease of the reaction rate in series 1. The structural and substituent effects were also studied by using the density functional theory method, and together with kinetic data, it gave a better insight into the influence of the effect of both geometry and substituent on the pi-electron density shift induced reactivity of investigated acids. geometry and substituent on the pi-electron density shift induced reactivity of investigated acids.
PB  - Wiley, Hoboken
T2  - International Journal of Chemical Kinetics
T1  - A LFER Kinetic Study of The Reaction of 5-Substituted Orotic Acids with Diazodiphenylmethane
EP  - 378
IS  - 7
SP  - 367
VL  - 48
DO  - 10.1002/kin.20997
ER  - 

@article{
author = "Assaleh, Fathi H. and Marinković, Aleksandar and Nikolić, Jasmina and Drmanić, Saša and Brković, Danijela V and Prlainović, Nevena and Jovanović, Bratislav Ž.",
year = "2016",
abstract = "Linear free energy relationships (LFER) were applied to the kinetic data for the reaction of 5-substituted orotic acids, series 1, with diazodiphenylmethane (DDM) in N,N-dimethylformamide and compared with results obtained for 2-substituted benzoic acids, series 2. The correlation analysis of the kinetic data with sigma substituent parameters was carried out using SSP (single substituent parameter) methods. From the sign and value of proportinality constant rho, lower sensitivity to the substituent effect was obtained in series 1, 0.876, than in the series 2, 1.877. Evaluation of substituent "ortho-effect" was performed using the Charton model, which includes the steric substituent parameter, and Fujita and Nishioka's model, which describes the total ortho-effect as contribution of ordinary polar effect, the ortho-steric and ortho-polar effects. Results of correlations, obtained by using the Charton model, showed highest contribution of the polar effect, 0.861 vs. 2.101, whereas the steric effect is of lowest significance, 0.117 vs. 0.055, for series 1 and 2, respectively. Also, a low negative value of coefficient with the steric effect, -0.08, obtained from the Fujita-Nishioka model indicated low steric effect, influencing a decrease of the reaction rate in series 1. The structural and substituent effects were also studied by using the density functional theory method, and together with kinetic data, it gave a better insight into the influence of the effect of both geometry and substituent on the pi-electron density shift induced reactivity of investigated acids. geometry and substituent on the pi-electron density shift induced reactivity of investigated acids.",
publisher = "Wiley, Hoboken",
journal = "International Journal of Chemical Kinetics",
title = "A LFER Kinetic Study of The Reaction of 5-Substituted Orotic Acids with Diazodiphenylmethane",
pages = "378-367",
number = "7",
volume = "48",
doi = "10.1002/kin.20997"
}

Assaleh, F. H., Marinković, A., Nikolić, J., Drmanić, S., Brković, D. V., Prlainović, N.,& Jovanović, B. Ž.. (2016). A LFER Kinetic Study of The Reaction of 5-Substituted Orotic Acids with Diazodiphenylmethane. in International Journal of Chemical Kinetics
Wiley, Hoboken., 48(7), 367-378.
https://doi.org/10.1002/kin.20997

Assaleh FH, Marinković A, Nikolić J, Drmanić S, Brković DV, Prlainović N, Jovanović BŽ. A LFER Kinetic Study of The Reaction of 5-Substituted Orotic Acids with Diazodiphenylmethane. in International Journal of Chemical Kinetics. 2016;48(7):367-378.
doi:10.1002/kin.20997 .

Assaleh, Fathi H., Marinković, Aleksandar, Nikolić, Jasmina, Drmanić, Saša, Brković, Danijela V, Prlainović, Nevena, Jovanović, Bratislav Ž., "A LFER Kinetic Study of The Reaction of 5-Substituted Orotic Acids with Diazodiphenylmethane" in International Journal of Chemical Kinetics, 48, no. 7 (2016):367-378,
https://doi.org/10.1002/kin.20997 . .