Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects
Само за регистроване кориснике
2004
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
H-1 NMR spectroscopy was used to investigate hydrogen bonding in the structurally related (Z)- and (E)-5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes consist of the intramolecularly H-bonded E-isomer and intermolecularly H-bonded Z-isomer in varying proportions which depend on the solvent polarity. For a representative of the series, (E)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone (1), the lack of a concentration and temperature dependence of the large chemical NH shift (delta 12.06ppm) in CDCl3 indicates strong intramolecular resonance-assisted hydrogen-bond formation (RAHB). The upfield chemical shifts of the NH proton of the (Z)-1 isomer as a function of temperature increase and the large 1H NMR Deltadelta/DeltaT value (-11.82ppbdegreesC(-1), Z/E=60:40, or -10.33ppbdegreesC(-1), Z/E = 20: 80) in CDCl3 are explained in terms of a decrease in intermolecular H-bonding resu...lting in a greater amount of free or unassociated Z-isomer. Copyright (C) 2004 John Wiley Sons, Ltd.
Кључне речи:
push-pull alkenes / Z/E isomerization / hydrogen bonding / temperature effect / H-1 NMR spectroscopyИзвор:
Journal of Physical Organic Chemistry, 2004, 17, 2, 118-123Издавач:
- John Wiley & Sons Ltd, Chichester
DOI: 10.1002/poc.700
ISSN: 0894-3230
WoS: 000188820800005
Scopus: 2-s2.0-0442280598
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Shirazi, A AU - Džambaski, Z. AU - Baranac-Stojanović, Marija AU - Minić, Dragica M. PY - 2004 UR - https://cherry.chem.bg.ac.rs/handle/123456789/567 AB - H-1 NMR spectroscopy was used to investigate hydrogen bonding in the structurally related (Z)- and (E)-5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes consist of the intramolecularly H-bonded E-isomer and intermolecularly H-bonded Z-isomer in varying proportions which depend on the solvent polarity. For a representative of the series, (E)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone (1), the lack of a concentration and temperature dependence of the large chemical NH shift (delta 12.06ppm) in CDCl3 indicates strong intramolecular resonance-assisted hydrogen-bond formation (RAHB). The upfield chemical shifts of the NH proton of the (Z)-1 isomer as a function of temperature increase and the large 1H NMR Deltadelta/DeltaT value (-11.82ppbdegreesC(-1), Z/E=60:40, or -10.33ppbdegreesC(-1), Z/E = 20: 80) in CDCl3 are explained in terms of a decrease in intermolecular H-bonding resulting in a greater amount of free or unassociated Z-isomer. Copyright (C) 2004 John Wiley Sons, Ltd. PB - John Wiley & Sons Ltd, Chichester T2 - Journal of Physical Organic Chemistry T1 - Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects VL - 17 IS - 2 SP - 118 EP - 123 DO - 10.1002/poc.700 ER -
@article{ author = "Marković, R. and Shirazi, A and Džambaski, Z. and Baranac-Stojanović, Marija and Minić, Dragica M.", year = "2004", abstract = "H-1 NMR spectroscopy was used to investigate hydrogen bonding in the structurally related (Z)- and (E)-5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these typical push-pull alkenes consist of the intramolecularly H-bonded E-isomer and intermolecularly H-bonded Z-isomer in varying proportions which depend on the solvent polarity. For a representative of the series, (E)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone (1), the lack of a concentration and temperature dependence of the large chemical NH shift (delta 12.06ppm) in CDCl3 indicates strong intramolecular resonance-assisted hydrogen-bond formation (RAHB). The upfield chemical shifts of the NH proton of the (Z)-1 isomer as a function of temperature increase and the large 1H NMR Deltadelta/DeltaT value (-11.82ppbdegreesC(-1), Z/E=60:40, or -10.33ppbdegreesC(-1), Z/E = 20: 80) in CDCl3 are explained in terms of a decrease in intermolecular H-bonding resulting in a greater amount of free or unassociated Z-isomer. Copyright (C) 2004 John Wiley Sons, Ltd.", publisher = "John Wiley & Sons Ltd, Chichester", journal = "Journal of Physical Organic Chemistry", title = "Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects", volume = "17", number = "2", pages = "118-123", doi = "10.1002/poc.700" }
Marković, R., Shirazi, A., Džambaski, Z., Baranac-Stojanović, M.,& Minić, D. M.. (2004). Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects. in Journal of Physical Organic Chemistry John Wiley & Sons Ltd, Chichester., 17(2), 118-123. https://doi.org/10.1002/poc.700
Marković R, Shirazi A, Džambaski Z, Baranac-Stojanović M, Minić DM. Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects. in Journal of Physical Organic Chemistry. 2004;17(2):118-123. doi:10.1002/poc.700 .
Marković, R., Shirazi, A, Džambaski, Z., Baranac-Stojanović, Marija, Minić, Dragica M., "Configurational isomerization of push-pull thiazoliclinone derivatives controlled by intermolecular and-intramolecular RAHB: H-1 NMR dynamic investigation of concentration and temperature effects" in Journal of Physical Organic Chemistry, 17, no. 2 (2004):118-123, https://doi.org/10.1002/poc.700 . .