29th Iranian Organic Chemistry Conference , 2023-11-01

Title : ( Crystal structure of a new diazaphosphorinane-based amidophosphoester: (C6H5O)(C10H6)(NH)2P(O) )

Authors: Fahimeh Sabbaghi , Mehrdad Pourayoubi ,

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Crystal structure of a new diazaphosphorinane-based amidophosphoester: (C6H5O)(C10H6)(NH)2P(O) Fahimeh Sabbaghia* and Mehrdad Pourayoubib a) Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran, email: fahimeh_sabbaghi@yahoo.com b) Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran, email: pourayoubi@um.ac.ir Keywords: Amidophosphoester, Diazaphosphorinane, X-ray crystallography Amidophosphoester moieties are structural motifs often found in a variety of bioactive products as well as in different classes of drugs [1]. In this work, the crystal structure of a new diazaphosphorinane-holding amidophosphoester with the formula (C6H5O)(C10H6)(NH)2P(O) is studied (Figure). The asymmetric unit is composed of three independent molecules, which are similar in viewpoint of bond lengths/angles. The main differences of these molecules are related to some torsion angles, especially the ones defining the orientation of C6H5O moiety with regard to the P═O group. The C—O—P═O torsion angles of 167.1 (5)°, –66.1 (5)° and –78.8 (6)° show the +ap, –sc and –sc conformations (ap = antiperiplanar and sc = synclinal). Thus, the distances of phenyl groups (of C6H5O segments) from the naphthalene rings are different in three symmetry-independent molecules. In the crystal structure, the molecules are aggregated through N—H…O═P hydrogen bonds in a tape arrangement. This assembly includes eight-membered ring hydrogen bond motifs, constructed from connection between both symmetry-related and symmetry-independent molecules. The P═O groups take part as a double-hydrogen bond acceptor. Figure: The molecular structure of asymmetric unit of the title compound, atom color codes: P orange, O red, N blue, and H pink. References [1] Warren, T. K.; Jordan, R.; Lo, M. K.; Ray, A. S.; Mackman, R. L.; Soloveva, V.; et al. Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys. Nature, 2016, 531, 381–385.


, Amidophosphoester, Diazaphosphorinane, X-ray crystallography
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author = {فهیمه صباغی and Pourayoubi, Mehrdad},
title = {Crystal structure of a new diazaphosphorinane-based amidophosphoester: (C6H5O)(C10H6)(NH)2P(O)},
booktitle = {29th Iranian Organic Chemistry Conference},
year = {2023},
location = {قم, IRAN},
keywords = {Amidophosphoester; Diazaphosphorinane; X-ray crystallography},


%0 Conference Proceedings
%T Crystal structure of a new diazaphosphorinane-based amidophosphoester: (C6H5O)(C10H6)(NH)2P(O)
%A فهیمه صباغی
%A Pourayoubi, Mehrdad
%J 29th Iranian Organic Chemistry Conference
%D 2023