18th Iranian Inorganic Chemistry Conference , 2017-03-07

Title : ( New single-enantiomer, racemic and diastereomer phosphorus-nitrogen compounds )

Authors: Fatemeh Karimi Ahamadabad , Mehrdad Pourayoubi , Marek Nečas , Monika Kučeraková , Michal Dušek ,

Citation: BibTeX | EndNote

Abstract

Chirality (handedness) is ubiquitous in nature at the molecular level. Many essential biochemical substances such as natural amino acids are chiral. In recent years, the optically active compounds have attracted remarkably attention due to their uses in the production of chiral drugs, polymers, inorganic compounds and advanced materials. In this work, two racemic phosphorus-chlorine reagents, rac-ClP(O)(OC6H5)(cyclo-NHC6H11) (I1) and rac-ClP(O)(OC6H5)(NHC6H4-p-CH3) (I2) and two single-enantiomer phosphorus-chlorine reagents, ClP(O)(R-(+){NHCH(CH3)(C6H5)}2 (I3) and ClP(O)(S-(-){NHCH(CH3)(C6H5)}2 (I4) were prepared and characterized. In the next step, four mixed-amide phosphinates rac-XP(O)(OC6H5)(cyclo-NHC6H11) [X = NH(cyclo-C5H9) (1), NHC5H9-4-CH3 (2)] and rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH2CH3)2 (3) and N(CH2C6H5)2 (4)] were synthesized and characterized by single crystal X-ray diffraction. Two pairs of diastereomer phosphorus-nitrogen compounds {R-(+)(C6H5)CH(CH3)NH}P(O)(OC6H5)(cyclo-NHC6H11) [5a (RR) & 5b (RS)] and {S-(-)(C6H5)CH(CH3)NH}P(O)(OC6H5)(NHC6H4-p-CH3) [6a (SR) & 6b (SS)] were prepared. In all structures, the P atom is in a chiral environment, resulting from two amido and one phenoxy bonded to phosphorus. In the four structures 5a, 5b, 6a & 6b there are two chiral centers on the P and C atoms.

Keywords

, Chirality, Racemic compound, Single crystal X-ray analysis
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@inproceedings{paperid:1063113,
author = {Karimi Ahamadabad, Fatemeh and Pourayoubi, Mehrdad and Marek Nečas and Monika Kučeraková and Michal Dušek},
title = {New single-enantiomer, racemic and diastereomer phosphorus-nitrogen compounds},
booktitle = {18th Iranian Inorganic Chemistry Conference},
year = {2017},
location = {مشهد, IRAN},
keywords = {Chirality; Racemic compound; Single crystal X-ray analysis},
}

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%0 Conference Proceedings
%T New single-enantiomer, racemic and diastereomer phosphorus-nitrogen compounds
%A Karimi Ahamadabad, Fatemeh
%A Pourayoubi, Mehrdad
%A Marek Nečas
%A Monika Kučeraková
%A Michal Dušek
%J 18th Iranian Inorganic Chemistry Conference
%D 2017

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