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. (24th March 2013)

• Record Type: Journal Article
• Authors: Pourayoubi, Mehrdad; Toghraee, Maryam; Divjakovic, Vladimir; van der Lee, Arie; Mancilla Percino, Teresa; Leyva Ramírez, Marco A.; Saneei, Anahid
• Is Part Of: Acta crystallographica. Volume 69:Part 2(2013:Apr.)
• Page Start: 184
• Page End: 194
• Publication Date: 2013-03-24
• Subjects: Crystallography -- Periodicals; Crystallization -- Periodicals; Chemical structure -- Periodicals; Solid state physics -- Periodicals; 530.41105
• DOI: 10.1107/S0108768113002656
• Languages: English
• ISSNs: 0108-7681

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formula <italic>X</italic>C(O)NHP(O)<italic>Y</italic> [<italic>X</italic> = CF<sub>3</sub> (1) and CClF<sub>2</sub> (2), <italic>Y</italic> = NHCH<sub>2</sub>C(CH<sub>3</sub>)<sub>2</sub>CH<sub>2</sub>NH] involving a 1, 3‐diazaphosphorinane ring part, and three 2, 6‐Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>C(O)NHP(O)<italic>Z</italic><sub>2</sub> phosphoric triamides [<italic>Z</italic> = NHC(CH<sub>3</sub>)<sub>3</sub> (3), N(CH<sub>3</sub>)(C<sub>6</sub>H<sub>11</sub>) (4) and N(CH<sub>3</sub>)(CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>) (5)]. The characterization was performed by <sup>31</sup>P{<sup>1</sup>H}, <sup>1</sup>H, <sup>13</sup>C NMR, IR spectroscopy besides <sup>19</sup>F 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 <italic>sp</italic><sup>2</sup> 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)]<sub>2</sub> or C(O)—NH—P(O)[NH(C)]<sub>2</sub>. The participation of N<sub>CP</sub>—H...O=P [N<sub>CP</sub> = the nitrogen atom of the C(O)—NH—P(O) fragment], N—H...O=P, N—H...O=C and N<sub>CP</sub>—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 [N<sub>CP</sub>—H][N—H]...O=P, [N—H]<sub>2</sub>...O=P, [N—H]<sub>2</sub>...O=C and [N—H]<sub>3</sub>...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 <italic>versus</italic> N...O distances are studied.</p> </abstract>