Publication details

Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)(2)P(O)(N)-based structures

Authors

SABBAGHI Fahimeh POURAYOUBI Mehrdad NEČAS Marek DAMODARAN Krishnan

Year of publication 2019
Type Article in Periodical
Magazine / Source ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
MU Faculty or unit

Faculty of Science

Citation
Web Full Text
Doi http://dx.doi.org/10.1107/S205322961801673X
Keywords single enantiomer; amidophosphoester; phosphate; hydrogen bonding; crystal structure; NMR; diastereotopic
Description The crystal structures of two single-enantiomer amidophosphoesters with an (O)(2)P(O)(N) skeleton, i. e. diphenyl [(R)-(+)-alpha-methylbenzylamido] phosphate, (I), and diphenyl [(S)-(-)-alpha-methylbenzylamido] phosphate, (II), both C20H20-NO3P, are reported. In both structures, chiral one-dimensional hydrogenbonded architectures, along [010], are mediated by N-H center dot center dot center dot OP interactions. The statistically identical assemblies include the noncentrosymmetric graph-set motif C(4) and the compounds crystallize in the chiral space group P21. As a result of synergistic co-operation from C-H center dot center dot center dot O interactions, a two-dimensional superstructure is built including a noncentrosymmetric R-4(4)(22) hydrogenbonded 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 C6H5O groups are different, which is reflected in the different chemical shifts and some coupling constants.
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