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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F19%3A00109265" target="_blank" >RIV/00216224:14310/19:00109265 - isvavai.cz</a>

Výsledek na webu

<a href="http://scripts.iucr.org/cgi-bin/paper?S205322961801673X" target="_blank" >http://scripts.iucr.org/cgi-bin/paper?S205322961801673X</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1107/S205322961801673X" target="_blank" >10.1107/S205322961801673X</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY

ISSN

2053-2296

e-ISSN

—

Svazek periodika

75

Číslo periodika v rámci svazku

JAN 2019

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

77-84

Kód UT WoS článku

000454742800012

EID výsledku v databázi Scopus

2-s2.0-85059295399