Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane
Abstract
The rate constants for the reaction of 2-methyl-cyclohex-1-enylcarboxylic, 2-phenylcyclohex-1-enylcarboxylic, and 2-methylbenzoic and 2-phenylbenzoic acids with diazodiphenyl-methane were determined in 14 various solvents at 30 degrees C. To explain the kinetic results through solvent effects, the second-order rate constants of the examined acids were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The quantitative relationship between the molecular structure and the chemical reactivity has been discussed, as well as the effect of geometry on the reactivity of the examined molecules. The geometric data of all the examined compounds corresponding to the energy minima in solvent, simulated as dielectric continuum, obtained using semiempirical MNDO-PM3 energy calc...ulations.
Source:
International Journal of Chemical Kinetics, 2007, 39, 12, 664-671Publisher:
- Wiley, Hoboken
Funding / projects:
- Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-MESTD-MPN2006-2010-142010)
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-MPN2006-2010-142063)
DOI: 10.1002/kin.20281
ISSN: 0538-8066
WoS: 000251341100003
Scopus: 2-s2.0-35948993754
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Nikolić, Jasmina AU - Ušćumlić, Gordana AU - Juranić, Ivan PY - 2007 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1144 AB - The rate constants for the reaction of 2-methyl-cyclohex-1-enylcarboxylic, 2-phenylcyclohex-1-enylcarboxylic, and 2-methylbenzoic and 2-phenylbenzoic acids with diazodiphenyl-methane were determined in 14 various solvents at 30 degrees C. To explain the kinetic results through solvent effects, the second-order rate constants of the examined acids were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The quantitative relationship between the molecular structure and the chemical reactivity has been discussed, as well as the effect of geometry on the reactivity of the examined molecules. The geometric data of all the examined compounds corresponding to the energy minima in solvent, simulated as dielectric continuum, obtained using semiempirical MNDO-PM3 energy calculations. PB - Wiley, Hoboken T2 - International Journal of Chemical Kinetics T1 - Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane EP - 671 IS - 12 SP - 664 VL - 39 DO - 10.1002/kin.20281 ER -
@article{ author = "Nikolić, Jasmina and Ušćumlić, Gordana and Juranić, Ivan", year = "2007", abstract = "The rate constants for the reaction of 2-methyl-cyclohex-1-enylcarboxylic, 2-phenylcyclohex-1-enylcarboxylic, and 2-methylbenzoic and 2-phenylbenzoic acids with diazodiphenyl-methane were determined in 14 various solvents at 30 degrees C. To explain the kinetic results through solvent effects, the second-order rate constants of the examined acids were correlated using the Kamlet-Taft solvatochromic equation. The correlations of the kinetic data were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The quantitative relationship between the molecular structure and the chemical reactivity has been discussed, as well as the effect of geometry on the reactivity of the examined molecules. The geometric data of all the examined compounds corresponding to the energy minima in solvent, simulated as dielectric continuum, obtained using semiempirical MNDO-PM3 energy calculations.", publisher = "Wiley, Hoboken", journal = "International Journal of Chemical Kinetics", title = "Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane", pages = "671-664", number = "12", volume = "39", doi = "10.1002/kin.20281" }
Nikolić, J., Ušćumlić, G.,& Juranić, I.. (2007). Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane. in International Journal of Chemical Kinetics Wiley, Hoboken., 39(12), 664-671. https://doi.org/10.1002/kin.20281
Nikolić J, Ušćumlić G, Juranić I. Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane. in International Journal of Chemical Kinetics. 2007;39(12):664-671. doi:10.1002/kin.20281 .
Nikolić, Jasmina, Ušćumlić, Gordana, Juranić, Ivan, "Solvent and structural effects on the kinetics of the reactions of 2-substituted cyclohex-1-enylcarboxylic and 2-substituted benzoic acids with diazodiphenyl with diazodiphenylmethane" in International Journal of Chemical Kinetics, 39, no. 12 (2007):664-671, https://doi.org/10.1002/kin.20281 . .