21th iranian inorganic chemistry seminar , 2019-08-28

Title : ( Synthesis, spectroscopic characterization and crystal structure of a new chiral amidophosphoester )

Authors: negin lal zakaria , Mehrdad Pourayoubi , Erika Samolova ,

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Abstract

The chiral amidophosphoester families have found widespread use in the preparation of different classes of drugs, and for processing of biologically active compounds [1]. We report here the synthesis of single-enantiomer amidophosphoester (C6H5O)2P(O)[(R)-(+)-NHCH(CH3)(C6H4-4-CH3)] (I) and its characterization by IR, NMR, mass, optical rotation and single crystal X-ray diffraction. The compound crystallizes in monoclinic system with chiral space group P21. The asymmetric unit is composed of two independent molecules. The P atoms have a distorted tetrahedral (O)2P(O)(N) configuration. In the crystal, chiral one-dimensional hydrogen-bonded architecture, formed along b axis, is mediated by classical N—H…O(P) and weak C—H…O(P) hydrogen bonds. This architecture includes D_1^1 (2), R_2^2 (10), C_2^2(8) and C_2^1 (8) graph-set motifs. In the IR spectrum, the band centered at 3174 cm–1 is attributed to the NH stretching frequency. The melting point of title structure (393 K) is a few lower than the closely related analogous compound (C6H5O)2P(O)[(R)-(+)NHCH(CH3)(C6H5)]2 (408 K) [2]. The phosphorus signal appears at –0.07 ppm, in comparison with the signal at –0.81 ppm for this analogous compound noted [2]. The two diastereotopic phenyl groups reveal two sets of signals in 1H- and 13C{1H}-NMR spectra. The specific optical rotation is measured as 〖[α]〗_D^20 = 51° (c 0.009, MeOH).

Keywords

, amidophosphoester, chirality, NMR, X-ray crystallography.
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@inproceedings{paperid:1075614,
author = {Lal Zakaria, Negin and Pourayoubi, Mehrdad and اریکا سامولووا},
title = {Synthesis, spectroscopic characterization and crystal structure of a new chiral amidophosphoester},
booktitle = {21th iranian inorganic chemistry seminar},
year = {2019},
location = {اراک, IRAN},
keywords = {amidophosphoester; chirality; NMR; X-ray crystallography.},
}

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%0 Conference Proceedings
%T Synthesis, spectroscopic characterization and crystal structure of a new chiral amidophosphoester
%A Lal Zakaria, Negin
%A Pourayoubi, Mehrdad
%A اریکا سامولووا
%J 21th iranian inorganic chemistry seminar
%D 2019

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