Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, Volume (69), No (2), Year (2013-4) , Pages (184-194)

Title : ( Analysis of N—H…O hydrogen bonds in new C(O)—NH—P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database )

Authors: Mehrdad Pourayoubi , maryam toghraee , Vladimir Divjakovic , Arie van der Lee , Teresa Mancilla Percino , Marco A. Leyva Ramírez , Anahid Saneei ,

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Abstract

Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formula XC(O)NHP(O)Y [X = CF3 (1) and CClF2 (2), Y = NHCH2C(CH3)2CH2NH] involving a 1,3-diazaphosphorinane ring part, and three 2,6-Cl2C6H3C(O)NHP(O)Z2 phosphoric triamides [Z = NHC(CH3)3 (3), N(CH3)(C6H11) (4) and N(CH3)(CH2C6H5) (5)]. The characterization was performed by 31P{1H}, 1H, 13C NMR, IR spectroscopy besides 19F NMR for fluorine containing compounds (1) and (2), and X-ray single-crystal structure analysis for (1), (3), (4) and (5). In each molecule the P atom has a distorted tetrahedral environment. The N atoms bonded to P atom have mainly sp2 character with a very slight tendency to a pyramidal coordination for some amido groups. Different types of N—H…O hydrogen bonds have been analyzed for (1), (3), (4) and (5) and 118 other structures (including 194 hydrogen bonds) deposited in the Cambridge Structural Database, containing either C(O)—NH—P(O)[N(C)(C)]2 or C(O)—NH—P(O)[NH(C)]2. The participation of NCP—H…O P [NCP = the nitrogen atom of the C(O)—NH—P(O) fragment], N—H…O═P, N—H…O═C and NCP—H…O═C hydrogen bonds in different hydrogen-bonded motifs are discussed. Moreover, the involvement of the O atoms of C═O or P═O in the [NCP—H][N—H]…O═P, [N—H]2…O═P, [N—H]2…O═C and [N—H]3…O═C groups are considered. A histogram of N…O distances, the distribution of N—H…O angles and the scatterplot of N—H…O angles versus N…O distances are studied.

Keywords

, C(O)—NH—P(O)-based phosphoric triamides, CSD, X-ray crystallography, N-H...O hydrogen bond
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@article{paperid:1034164,
author = {Pourayoubi, Mehrdad and Toghraee, Maryam and Vladimir Divjakovic and Arie Van Der Lee and Teresa Mancilla Percino and Marco A. Leyva Ramírez and Saneei, Anahid},
title = {Analysis of N—H…O hydrogen bonds in new C(O)—NH—P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database},
journal = {Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials},
year = {2013},
volume = {69},
number = {2},
month = {April},
issn = {2052-5206},
pages = {184--194},
numpages = {10},
keywords = {C(O)—NH—P(O)-based phosphoric triamides; CSD; X-ray crystallography; N-H...O hydrogen bond},
}

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%0 Journal Article
%T Analysis of N—H…O hydrogen bonds in new C(O)—NH—P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database
%A Pourayoubi, Mehrdad
%A Toghraee, Maryam
%A Vladimir Divjakovic
%A Arie Van Der Lee
%A Teresa Mancilla Percino
%A Marco A. Leyva Ramírez
%A Saneei, Anahid
%J Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
%@ 2052-5206
%D 2013

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