The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane
Само за регистроване кориснике
1985
Чланак у часопису (Објављена верзија)
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Приказ свих података о документуАпстракт
The conformational equilibrium has been measured for r-1,c-3-dichloro-t-5-methylcyclohexane(2) in six solvents from the 500 MHz and 400 MHz 1H NMR spectra. The room-temperature and low-temperature C1H couplings are used as well as the vicinal proton-proton coupling constants based on the MM2-calculated dihedral angles and the empirically generalized Karplus equation. The equilibrium exhibits a very weak solvent dependence; ΔGaa-ee varies from 1.22 kcal mol-1 in CDCl3 to 0.87 kcal mol-1 in DMSO-d6. The free energy difference, Δaa-ee II 0.90 kcal mol-1, in CD2Cl2 is determined by peak-area NMR measurements at -100°C. The reaction field theory is used to calculate the variation of Δaa-ee with solvent polarity. The calculated solvent shift δΔGaa-ee (CDCl3 to DMSO-d6) is -0.21 kcal mol-1, compared with -0.35 kcal mol-1 determined experimentally.
Кључне речи:
solvent effect / conformational equilibrium / proton / Karplus equationИзвор:
Journal of Molecular Structure, 1985, 131, 3-4, 261-266Издавач:
- Elsevier
Институција/група
IHTMTY - JOUR AU - Došen-Mićović, Ljiljana AU - Jeremić, D. PY - 1985 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4519 AB - The conformational equilibrium has been measured for r-1,c-3-dichloro-t-5-methylcyclohexane(2) in six solvents from the 500 MHz and 400 MHz 1H NMR spectra. The room-temperature and low-temperature C1H couplings are used as well as the vicinal proton-proton coupling constants based on the MM2-calculated dihedral angles and the empirically generalized Karplus equation. The equilibrium exhibits a very weak solvent dependence; ΔGaa-ee varies from 1.22 kcal mol-1 in CDCl3 to 0.87 kcal mol-1 in DMSO-d6. The free energy difference, Δaa-ee II 0.90 kcal mol-1, in CD2Cl2 is determined by peak-area NMR measurements at -100°C. The reaction field theory is used to calculate the variation of Δaa-ee with solvent polarity. The calculated solvent shift δΔGaa-ee (CDCl3 to DMSO-d6) is -0.21 kcal mol-1, compared with -0.35 kcal mol-1 determined experimentally. PB - Elsevier T2 - Journal of Molecular Structure T1 - The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane VL - 131 IS - 3-4 SP - 261 EP - 266 DO - 10.1016/0022-2860(85)87027-7 ER -
@article{ author = "Došen-Mićović, Ljiljana and Jeremić, D.", year = "1985", abstract = "The conformational equilibrium has been measured for r-1,c-3-dichloro-t-5-methylcyclohexane(2) in six solvents from the 500 MHz and 400 MHz 1H NMR spectra. The room-temperature and low-temperature C1H couplings are used as well as the vicinal proton-proton coupling constants based on the MM2-calculated dihedral angles and the empirically generalized Karplus equation. The equilibrium exhibits a very weak solvent dependence; ΔGaa-ee varies from 1.22 kcal mol-1 in CDCl3 to 0.87 kcal mol-1 in DMSO-d6. The free energy difference, Δaa-ee II 0.90 kcal mol-1, in CD2Cl2 is determined by peak-area NMR measurements at -100°C. The reaction field theory is used to calculate the variation of Δaa-ee with solvent polarity. The calculated solvent shift δΔGaa-ee (CDCl3 to DMSO-d6) is -0.21 kcal mol-1, compared with -0.35 kcal mol-1 determined experimentally.", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane", volume = "131", number = "3-4", pages = "261-266", doi = "10.1016/0022-2860(85)87027-7" }
Došen-Mićović, L.,& Jeremić, D.. (1985). The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane. in Journal of Molecular Structure Elsevier., 131(3-4), 261-266. https://doi.org/10.1016/0022-2860(85)87027-7
Došen-Mićović L, Jeremić D. The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane. in Journal of Molecular Structure. 1985;131(3-4):261-266. doi:10.1016/0022-2860(85)87027-7 .
Došen-Mićović, Ljiljana, Jeremić, D., "The solvent effect on the conformational equilibrium of 1,3-dichloro-5-methylcylclohexane" in Journal of Molecular Structure, 131, no. 3-4 (1985):261-266, https://doi.org/10.1016/0022-2860(85)87027-7 . .