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Two single‐enantiomer amidophosphoesters: a database study on the chirality of (O) 2 P(O)(N)‐based structures
Author(s) -
Sabbaghi Fahimeh,
Pourayoubi Mehrdad,
Nečas Marek,
Damodaran Krishnan
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s205322961801673x
Subject(s) - chirality (physics) , enantiomer , chemistry , hydrogen bond , crystallography , stereochemistry , crystal structure , space group , molecule , x ray crystallography , chiral symmetry , physics , organic chemistry , diffraction , quantum mechanics , nambu–jona lasinio model , optics , quark
The crystal structures of two single‐enantiomer amidophosphoesters with an (O) 2 P(O)(N) skeleton, i.e. diphenyl [( R )‐(+)‐α‐methylbenzylamido]phosphate, (I), and diphenyl [( S )‐(−)‐α‐methylbenzylamido]phosphate, (II), both C 20 H 20 NO 3 P, are reported. In both structures, chiral one‐dimensional hydrogen‐bonded architectures, along [010], are mediated by N—H…OP interactions. The statistically identical assemblies include the noncentrosymmetric graph‐set motif C (4) and the compounds crystallize in the chiral space group P 2 1 . As a result of synergistic co‐operation from C—H…O interactions, a two‐dimensional superstructure is built including a noncentrosymmetric R 4 4 (22) hydrogen‐bonded motif. A Cambridge Structural Database survey was performed on (O) 2 P(O)(N)‐based structures in order to review the frequency of space groups observed in this family of compounds; the hydrogen‐bond motifs in structures with chiral space groups and the types of groups inducing chirality are discussed. The 2,3 J X –P ( X = H or C) coupling constants from the NMR spectra of (I) and (II) have been studied. In each compound, the two diastereotopic C 6 H 5 O groups are different, which is reflected in the different chemical shifts and some coupling constants.