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

J 2019

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

SABBAGHI, Fahimeh; Mehrdad POURAYOUBI; Marek NEČAS a Krishnan DAMODARAN

Základní údaje

Originální název

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

Autoři

SABBAGHI, Fahimeh (364 Írán); Mehrdad POURAYOUBI (364 Írán); Marek NEČAS (203 Česká republika, garant, domácí) a Krishnan DAMODARAN (840 Spojené státy)

Vydání

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, CHESTER, INT UNION CRYSTALLOGRAPHY, 2019, 2053-2296

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Full Text

Impakt faktor

Impact factor: 1.090

Kód RIV

RIV/00216224:14310/19:00109265

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1107/S205322961801673X

UT WoS

000454742800012

EID Scopus

2-s2.0-85059295399

Klíčová slova anglicky

single enantiomer; amidophosphoester; phosphate; hydrogen bonding; crystal structure; NMR; diastereotopic

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 11. 5. 2020 13:18, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

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.

Návaznosti

MUNI/A/1467/2014, interní kód MU

Název: Pokročilé metody syntézy a komplexní studium vlastností molekulárních a nanostrukturních systémů (Akronym: Monasyst)

Investor: Masarykova univerzita, Pokročilé metody syntézy a komplexní studium vlastností molekulárních a nanostrukturních systémů, DO R. 2020_Kategorie A - Specifický výzkum - Studentské výzkumné projekty

Citovat

SABBAGHI, Fahimeh; Mehrdad POURAYOUBI; Marek NEČAS a Krishnan DAMODARAN. Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)(2)P(O)(N)-based structures. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY. CHESTER: INT UNION CRYSTALLOGRAPHY, 2019, roč. 75, JAN 2019, s. 77-84. ISSN 2053-2296. Dostupné z: https://doi.org/10.1107/S205322961801673X.

@article{1504910,
   author = {Sabbaghi, Fahimeh and Pourayoubi, Mehrdad and Nečas, Marek and Damodaran, Krishnan},
   article_location = {CHESTER},
   article_number = {JAN 2019},
   doi = {https://doi.org/10.1107/S205322961801673X},
   keywords = {single enantiomer; amidophosphoester; phosphate; hydrogen bonding; crystal structure; NMR; diastereotopic},
   language = {eng},
   issn = {2053-2296},
   journal = {ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY},
   title = {Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)(2)P(O)(N)-based structures},
   url = {http://scripts.iucr.org/cgi-bin/paper?S205322961801673X},
   volume = {75},
   year = {2019}
}

TY  - JOUR
ID  - 1504910
AU  - Sabbaghi, Fahimeh - Pourayoubi, Mehrdad - Nečas, Marek - Damodaran, Krishnan
PY  - 2019
TI  - Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)(2)P(O)(N)-based structures
JF  - ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
VL  - 75
IS  - JAN 2019
SP  - 77-84
EP  - 77-84
PB  - INT UNION CRYSTALLOGRAPHY
SN  - 20532296
KW  - single enantiomer
KW  - amidophosphoester
KW  - phosphate
KW  - hydrogen bonding
KW  - crystal structure
KW  - NMR
KW  - diastereotopic
UR  - http://scripts.iucr.org/cgi-bin/paper?S205322961801673X
L2  - http://scripts.iucr.org/cgi-bin/paper?S205322961801673X
N2  - 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.
ER  -

SABBAGHI, Fahimeh; Mehrdad POURAYOUBI; Marek NEČAS a Krishnan DAMODARAN. Two single-enantiomer amidophosphoesters: a database study on the chirality of (O)(2)P(O)(N)-based structures. \textit{ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY}. CHESTER: INT UNION CRYSTALLOGRAPHY, 2019, roč.~75, JAN 2019, s.~77-84. ISSN~2053-2296. Dostupné z: https://doi.org/10.1107/S205322961801673X.

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