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Dynamic Structure of Organic Compounds in Solution According to NMR Data and Quantum Chemical Calculations: III. Noradrenalineстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Дата последнего поиска статьи во внешних источниках: 21 мая 2019 г.
- Авторы: Ganina T.A., Chertkov V.A.
- Журнал: Russian Journal of Organic Chemistry, Pleiades Publishing ltd
- Том: 55
- Номер: 3
- Год издания: 2019
- Первая страница: 354
- Последняя страница: 361
- DOI: 10.1134/S107042801903014X
- Аннотация: Parameters of restricted internal rotation about the C–C bond of the O–C–C–N fragment in the neutral and protonated forms of noradrenaline in D2O, CD3OD, and DMSO-d6 were estimated by quantum molecular dynamics and NMR methods. The one-dimensional internal rotation potentials were calculated in the MP2/aug-cc-pVTZ approximation. The multiplet structure of the 1H NMR spectra of neutral and protonated noradrenaline in the given solvent series was resolved, and signals of diastereotopic methylene protons pro-S and pro-R were assigned. The conformational dependences of the proton coupling constants were calculated at the FPT-DFT 6-311++G(2df,2p) level of theory. The relative contributions of different rotamers were evaluated by solving a series of inverse vibrational problems in terms of the large-amplitude vibration model to achieve the best agreement between the calculated and experimental coupling constants. The neutral form of noradrenaline was shown to prefer conformation g+, while conformer g– was found to be the minor one. Protonation of noradrenaline molecule essentially stabilizes conformer g–. In all cases, the contribution of conformer t with transoid orientation of the oxygen and nitrogen atoms did not exceed 1%. The obtained data can be useful for the construction of a quantitative model for noradrenaline binding to receptors at the molecular level.
- Добавил в систему: Чертков Вячеслав Алексеевич