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 and Krishnan DAMODARAN

Basic information

Original name

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

Authors

SABBAGHI, Fahimeh (364 Islamic Republic of Iran), Mehrdad POURAYOUBI (364 Islamic Republic of Iran), Marek NEČAS (203 Czech Republic, guarantor, belonging to the institution) and Krishnan DAMODARAN (840 United States of America)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Full Text

Impact factor

Impact factor: 1.090

RIV identification code

RIV/00216224:14310/19:00109265

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1107/S205322961801673X

UT WoS

000454742800012

Keywords in English

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

Abstract

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.

Links

MUNI/A/1467/2014, interní kód MU

Name: Pokročilé metody syntézy a komplexní studium vlastností molekulárních a nanostrukturních systémů (Acronym: Monasyst)

Investor: Masaryk University, Category A

Citovat

SABBAGHI, Fahimeh, Mehrdad POURAYOUBI, Marek NEČAS and 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, vol. 75, JAN 2019, p. 77-84. ISSN 2053-2296. Available from: https://dx.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 = {http://dx.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 and 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, vol.~75, JAN 2019, p.~77-84. ISSN~2053-2296. Available from: https://dx.doi.org/10.1107/S205322961801673X.

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