Acta Crystallographica Section C: Structural Chemistry, ( ISI ), Volume (69), No (10), Year (2013-10) , Pages (1181-1185)

Title : ( New rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH3)(cyclo-C6H11) and NH(C3H5)] and rac-(C6H5CH2NH)-P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates )

Authors: Mehrdad Pourayoubi , fatemeh karimi , Hossein Eshtiagh Hosseini , Monika Kučeráková , Václav Eigner , Michal Dušek ,

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The mixed-amide phosphinates, rac-phenyl (N-methylcyclohexylamido)(p-tolylamido)phosphinate, C20H27N2O2P, (I), and rac-phenyl (allylamido)(p-tolylamido)phosphinate, C16H19N2O2P, (II), were synthesized from the racemic phosphorus–chlorine compound (R,S)-(Cl)P(O)(OC6H5)(NHC6H4-p-CH3). Furthermore, the phosphorus–chlorine compound ClP(O)(OC6H5)(NH-cyclo-C6H11) was synthesized for the first time and used for the synthesis of rac-phenyl (benzylamido)(cyclohexylamido)phosphinate, C19H25N2O2P, (III). The strategies for the synthesis of racemic mixed-amide phosphinates are discussed. The P atom in each compound is in a distorted tetrahedral (N1)P(═O)(O)(N2) environment. In (I) and (II), the p-tolylamido substituent makes a longer P—N bond than those involving the N-methylcyclohexylamido and allylamido substituents. In (III), the differences between the P—N bond lengths involving the cyclohexylamido and benzylamido substituents are not significant. In all three structures, the phosphoryl O atom takes part with theN—H unit in hydrogen bonding interactions, viz. an N—H…O═P hydrogen bond for (I) and (N—H)(N—H)…O═P hydrogen bonds for (II) and (III), building linear arrangements along [001] for (I) and along [010] for (III), and a ladder arrangement along [100] for (II).

Keywords

, crystal structure; racemic mixed, amide phosphinates; P—N bonds; N—H…O═P hydrogen
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@article{paperid:1037918,
author = {Pourayoubi, Mehrdad and Karimi, Fatemeh and Eshtiagh Hosseini, Hossein and Monika Kučeráková and Václav Eigner and Michal Dušek},
title = {New rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH3)(cyclo-C6H11) and NH(C3H5)] and rac-(C6H5CH2NH)-P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates},
journal = {Acta Crystallographica Section C: Structural Chemistry},
year = {2013},
volume = {69},
number = {10},
month = {October},
issn = {2053-2296},
pages = {1181--1185},
numpages = {4},
keywords = {crystal structure; racemic mixed-amide phosphinates; P—N bonds; N—H…O═P hydrogen bonds},
}

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%0 Journal Article
%T New rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH3)(cyclo-C6H11) and NH(C3H5)] and rac-(C6H5CH2NH)-P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates
%A Pourayoubi, Mehrdad
%A Karimi, Fatemeh
%A Eshtiagh Hosseini, Hossein
%A Monika Kučeráková
%A Václav Eigner
%A Michal Dušek
%J Acta Crystallographica Section C: Structural Chemistry
%@ 2053-2296
%D 2013

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