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Журнал структурной химии  / №1 2015

ULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL y-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES (300,00 руб.)

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Первый авторWahbi
АвторыSlimani H., Touil S.
Страниц8
ID359560
АннотацияWe report for the first time the synthesis of y-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with y-phosphonylketones. The full characterization of these compounds through their 1H, 31P, and 13C NMR spectra indicates that they are obtained as a mixture of Z and E isomers. An unambiguous method for the assignment of these configurations, based on the 13C chemical shifts of C2 carbon atoms in the a position with respect to the C=N double bond is used. The 31P chemical shifts are also of diagnostic importance in assigning the Z and E configurations. Indeed, the phosphorus atom is found to resonate at a slightly higher field in Z isomers.
УДК548.737:541.67
Wahbi, A. ULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL y-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES / A. Wahbi, H. Slimani, S. Touil // Журнал структурной химии .— 2015 .— №1 .— С. 41-48 .— URL: https://rucont.ru/efd/359560 (дата обращения: 06.12.2021)

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2015.  56,  1 UDC 548.737:541.67 MULTINUCLEAR NMR STRUCTURAL STUDY OF NOVEL t-IMINOPHOSPHONATE AND PHOSPHINE OXIDE DERIVATIVES A. Wahbi, H. Slimani, S. Touil Laboratory of Heteroatom Organic Chemistry, Department of Chemistry, Faculty of Sciences of Bizerta, University of Carthage, Jarzouna, Tunisia E-mail: soufiane.touil@fsb.rnu.tn Received August, 21, 2013 We report for the first time the synthesis of t-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with t-phosphonylketones. <...> The full characterization of these compounds through their 1H, 31P, and 13C NMR spectra indicates that they are obtained as a mixture of Z and E isomers. <...> An unambiguous method for the assignment of these configurations, based on the 13C chemical shifts of C2 carbon atoms in the h position with respect to the C=N double bond is used. <...> The 31P chemical shifts are also of diagnostic importance in assigning the Z and E configurations. <...> Indeed, the phosphorus atom is found to resonate at a slightly higher field in Z isomers. <...> INTRODUCTION Imines, also known as Schiff bases or azomethines, are very important compounds due to their broad spectrum of biological properties, including antimicrobial [ 1—4], antifungal [ 5, 6 ], anticancer [ 7—10], anti-HIV [ 11 ], and herbicidal [ 12 ] activities. <...> On the other hand, imines and their derivatives are recognized as key intermediates for the synthesis of biologically active nitrogen heterocycles such as those involved in alkaloid synthesis [16—19 ]. <...> The introduction of a phosphonate functionality on imines may be very interesting for the enhancement of the biological and complexing properties of these molecules, and for synthetic transformations leading to aminophosphonate derivatives and azaheterocyclic phosphonates which are known to exhibit a variety of pharmacological properties [ 20, 21 ]. <...> The configuration determination of the C=N double bond in imines is routinely accomplished using various experimental techniques, especially spectroscopic ones [22—24 ]. <...> In view of the above, and in the continuation of our studies on the preparation and potential synthetic applications of imines [25—27 ], we report here for the first time the synthesis of t-iminophosphonates and phosphine oxides from the acid-catalysed reaction of primary amines with t-phosphonylketones. <...> The full characterization of these compounds through their 1H, 31P, and 13C NMR spectra indicated that they were obtained as a mixture <...>