15th Iranian Chemistry Conference , 2011-09-04

Title : ( Synthesis and crystal structure of N-(2-fluorobenzoyl)-N\',N\'-diisopropylphosphoric triamide )

Authors: Atekeh Tarahhomi , Mehrdad Pourayoubi ,

Citation: BibTeX | EndNote

Abstract

Recently, the chemistry of phosphoramidates has been considered due to their antivirus and anticancer activities, their coordination chemistry and having a decisive role in catalytic and metabolism processes. Phosphoramidates of the general formula RC(O)NHP(O)X2, are potential O,O\'-donor ligands for metal complexation, particularly for lanthanide ions. Following the previous works about carbacylamidophosphates with a C(═O)NHP(═O) skeleton such as P(O)[NHC(O)C6H4(4-F)][HNC6H4CH3]2 and P(O)[NHC(O)C6H3(2,6-F2)][[HNC(CH3)]3]2, here, we report the synthesis and crystal structure of title compound, P(O)[NHC(O)C6H4(2-F)][HNCH(CH3)2]2. This compound appears as two crystallographically independent molecules (A and B) that in each one, the two intermolecular P=O…H―Namide and one C=O…H―NC(O)NHP(O) HBs are responsible to connection of the molecules together as 1-D chains. This result was opposite to that commonly observed for carbacylamido phosphates which show a tendency of phosphoryl group rather than the carbonyl counterpart to form hydrogen bond with the more acidic NH of C(O)NHP(O) skeleton, whereas, the NH of NHR\' unit is hydrogen-bonded to C(O). Molecules A and B are very close to each other from a structural point of view. The phosphoryl and carbonyl groups are anti to each other and the phosphorus atom has a distorted tetrahedral configuration. The bond angles around the P atom are in the range of 107.11 (8)° to 114.81 (8)°. The Pamide–N bond lengths (1.618(6) Å and 1.604(6) Å for A and 1.606(6) Å and 1.612(6) Å for B) are shorter than the P–NC(O)NHP(O) bond (1.705(4) Å for A and 1.698(5) Å for B). The P═O bond lengths (of 1.486(4) Å for A and 1.480(3) Å for B) are standard for phosphoramidate compounds.

Keywords

, Phosphoramidates, O, O\'-donor ligands, crystal structure, C(O)NHP(O) skeleton.
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@inproceedings{paperid:1024992,
author = {Tarahhomi, Atekeh and Pourayoubi, Mehrdad},
title = {Synthesis and crystal structure of N-(2-fluorobenzoyl)-N\',N\'-diisopropylphosphoric triamide},
booktitle = {15th Iranian Chemistry Conference},
year = {2011},
location = {همدان, IRAN},
keywords = {Phosphoramidates; O;O\'-donor ligands; crystal structure; C(O)NHP(O) skeleton.},
}

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%0 Conference Proceedings
%T Synthesis and crystal structure of N-(2-fluorobenzoyl)-N\',N\'-diisopropylphosphoric triamide
%A Tarahhomi, Atekeh
%A Pourayoubi, Mehrdad
%J 15th Iranian Chemistry Conference
%D 2011

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