Two single-enantiomer (R and S) Amidophosphoesters

سال انتشار: 1397
محل انتشار: بیستمین کنگره شیمی ایران
کد COI اختصاصی: IRANCC20_794
زبان مقاله: انگلیسی
تعداد مشاهده: 387

نویسندگان

Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran

Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

Department of Chemistry, Masaryk University, Kotlarska ۲, ۶۱۱۳۷ Brno, Czech Republic,CEITEC - Central European Institute of Technology, Masaryk University, Kamenice ۵, ۶۲۵۰۰ Brno, Czech Republic

Krishnan Damodaran

Department of Chemistry, University of Pittsburgh, Pittsburgh, PA ۱۵۲۶۰, USA

چکیده

The compound (C6H5O)2P(O)[NHCH(CH3)(C6H5)] exists in previously published papers, with together its melting point, elemental analysis and selected mass spectrum peaks, and with no sign of the type of NHCH(CH3)(C6H5) fragment as R, S or racemic. Here, the crystal structures of (C6H5O)2P(O)[NH(+)CH(CH3)(C6H5)] and (C6H5O)2P(O)[NH(–)CH(CH3)(C6H5)] are reported. The compounds are named as diphenyl (R-(+)-α-methylbenzylamido)phosphate, (I), and diphenyl (S-(–)-α-methylbenzylamido)phosphate, (II). In both structures, the chiral one-dimensional hydrogen-bonded architectures, along [010], are built from NH…OP interactions; however, they are mirror images of each other. The assemblies of these compounds include the non-centrosymmetric graph-set motif C(4) and the compounds crystallize in the chiral space group P21. Figure 1 shows the assembly of the structure (II), for a typical example. For each molecule, the two C6H5O groups bonded to phosphorus are different in NMR media (monitored by 1H and 13C NMR). For both compounds, the phosphorus signal exactly appears at –0.81 ppm (DMSO-d6), in a calibrated condition (concentration, temperature).

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