Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study
Vodonična veza u push-pull 5-supstituisanim 2-alkiliden-4-oksotiazolidinima: 1H-NMR spektroskopsko proučavanje
Abstract
Application of dynamic H-1-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alklidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these topical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series. (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone, a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied.
Primenom dinamičke 1H-NMR spektroskopije došlo se do boljeg razumevanja o vrsti vodoničnih veza koje postoje u strukturno sličnim 5-supstituisanim 2-alkiliden-4-oksotiazolidinima u polarnim i apolarnim rastvaračima. Uravnotežene smese ovih tipičnih push-pull alkena u CDCl3 sadrže (E)-izomer vezan intramolekulskom vodoničnom vezom kao i intermolekulski vodoničnom vezom vezan (Z)-izomer u različitim odnosima, koji zavise od polarnosti rastvarača. U slučaju tipičnog predstavnika serije (Z)-2-(5-etoksikarbonilmetil-4-oksotiazolidin- 2-iliden)-1-feniletanona uticaj koncentracije na stepen stvaranja intermolekulske vodonične veze u apolarnom CDCl3 je takođe proučavan.
Keywords:
push-pull alkenes / hydrogen bonding / hydrogen bonding / 1H-NMR spectroscopy / H-1-NMR spectroscopeSource:
Journal of the Serbian Chemical Society, 2003, 68, 1, 1-7Publisher:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0301001M
ISSN: 0352-5139
WoS: 000180807300001
Scopus: 2-s2.0-0037286126
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Shirazi, A AU - Džambaski, Z. AU - Baranac-Stojanović, Marija AU - Minić, Dragica M. PY - 2003 UR - https://cherry.chem.bg.ac.rs/handle/123456789/535 AB - Application of dynamic H-1-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alklidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these topical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series. (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone, a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied. AB - Primenom dinamičke 1H-NMR spektroskopije došlo se do boljeg razumevanja o vrsti vodoničnih veza koje postoje u strukturno sličnim 5-supstituisanim 2-alkiliden-4-oksotiazolidinima u polarnim i apolarnim rastvaračima. Uravnotežene smese ovih tipičnih push-pull alkena u CDCl3 sadrže (E)-izomer vezan intramolekulskom vodoničnom vezom kao i intermolekulski vodoničnom vezom vezan (Z)-izomer u različitim odnosima, koji zavise od polarnosti rastvarača. U slučaju tipičnog predstavnika serije (Z)-2-(5-etoksikarbonilmetil-4-oksotiazolidin- 2-iliden)-1-feniletanona uticaj koncentracije na stepen stvaranja intermolekulske vodonične veze u apolarnom CDCl3 je takođe proučavan. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study T1 - Vodonična veza u push-pull 5-supstituisanim 2-alkiliden-4-oksotiazolidinima: 1H-NMR spektroskopsko proučavanje VL - 68 IS - 1 SP - 1 EP - 7 DO - 10.2298/JSC0301001M ER -
@article{ author = "Marković, R. and Shirazi, A and Džambaski, Z. and Baranac-Stojanović, Marija and Minić, Dragica M.", year = "2003", abstract = "Application of dynamic H-1-NMR spectroscopy added to the understanding of the hydrogen bonds existing in the structurally related 5-substituted-2-alklidene-4-oxothiazolidines in polar and apolar solvents. The equilibrated mixtures of these topical push-pull alkenes in CDCl3 consist of the intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions which depend on the solvent polarity. For the representative of the series. (Z)-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone, a concentration effect on the degree of intermolecular hydrogen bonding in apolar CDCl3 has been studied., Primenom dinamičke 1H-NMR spektroskopije došlo se do boljeg razumevanja o vrsti vodoničnih veza koje postoje u strukturno sličnim 5-supstituisanim 2-alkiliden-4-oksotiazolidinima u polarnim i apolarnim rastvaračima. Uravnotežene smese ovih tipičnih push-pull alkena u CDCl3 sadrže (E)-izomer vezan intramolekulskom vodoničnom vezom kao i intermolekulski vodoničnom vezom vezan (Z)-izomer u različitim odnosima, koji zavise od polarnosti rastvarača. U slučaju tipičnog predstavnika serije (Z)-2-(5-etoksikarbonilmetil-4-oksotiazolidin- 2-iliden)-1-feniletanona uticaj koncentracije na stepen stvaranja intermolekulske vodonične veze u apolarnom CDCl3 je takođe proučavan.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study, Vodonična veza u push-pull 5-supstituisanim 2-alkiliden-4-oksotiazolidinima: 1H-NMR spektroskopsko proučavanje", volume = "68", number = "1", pages = "1-7", doi = "10.2298/JSC0301001M" }
Marković, R., Shirazi, A., Džambaski, Z., Baranac-Stojanović, M.,& Minić, D. M.. (2003). Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 68(1), 1-7. https://doi.org/10.2298/JSC0301001M
Marković R, Shirazi A, Džambaski Z, Baranac-Stojanović M, Minić DM. Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study. in Journal of the Serbian Chemical Society. 2003;68(1):1-7. doi:10.2298/JSC0301001M .
Marković, R., Shirazi, A, Džambaski, Z., Baranac-Stojanović, Marija, Minić, Dragica M., "Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: H-1-NMR spectroscopic study" in Journal of the Serbian Chemical Society, 68, no. 1 (2003):1-7, https://doi.org/10.2298/JSC0301001M . .