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Syntheses and structures of four new mixed‐amide phosphoric triamides
Author(s) -
Keikha Mojtaba,
Pourayoubi Mehrdad,
Tarahhomi Atekeh,
Lee Arie van der
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229616001595
Subject(s) - amide , chemistry , substituent , molecule , phosphoric acid , hydrogen bond , medicinal chemistry , x ray crystallography , stereochemistry , organic chemistry , diffraction , physics , optics
Phosphoric triamides have extensive applications in biochemistry and are also used as O ‐donor ligands. Four new mixed‐amide phosphoric triamide structures, namely rac ‐ N ‐ tert ‐butyl‐ N ′, N ′′‐dicyclohexyl‐ N ′′‐methylphosphoric triamide, C 17 H 36 N 3 OP, (I), rac ‐ N , N ′‐dicyclohexyl‐ N ′‐methyl‐ N ′′‐( p ‐tolyl)phosphoric triamide, C 20 H 34 N 3 OP, (II), N , N ′, N ′′‐tricyclohexyl‐ N ′′‐methylphosphoric triamide, C 19 H 38 N 3 OP, (III), and 2‐[cyclohexyl(methyl)amino]‐5,5‐dimethyl‐1,3,2λ 5 ‐diazaphosphinan‐2‐one, C 12 H 26 N 3 OP, (IV), have been synthesized and studied by X‐ray diffraction and spectroscopic methods. Structures (I) and (II) are the first diffraction studies of acyclic racemic mixed‐amide phosphoric triamides. The P—N bonds resulting from the different substituent –N(CH 3 )(C 6 H 11 ), (C 6 H 11 )NH–, 4‐CH 3 ‐C 6 H 4 NH–, ( tert ‐C 4 H 9 )NH– and –NHCH 2 C(CH 3 ) 2 CH 2 NH– groups are compared, along with the different molecular volumes and electron‐donor strengths. In all four structures, the molecules form extended chains through N—H…O hydrogen bonds.