CyclohexylmethylammoniumN,N′-dicyclohexyl-N,N′-dimethyl-N′′-(2,2,2-trifluoroacetyl)phosphonic triamide)

Yazdanbakhsh, Mohammad; Eshtiagh‐Hosseini, Hossein; Sabbaghi, Fahimeh

doi:10.1107/s1600536808040737

Cited by 3 publications

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“…The P═O and P-N bond lengths and the P-N-C bond angles are comparable to those in a similar previously reported proton transfer compound, {C 6 H 11 NH 2 CH 3 } + {CF 3 C(O)NP(O)[N(CH 3 )(C 6 H 11 )] 2 } - (Yazdanbakhsh et al, 2009).…”

Section: Data Collectionsupporting

confidence: 86%

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

et al. 2011

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In the anion of the title salt, C7H16N+·C21H35N3O3PS−, the P and S atoms are both in distorted tetrahedral environments and the angles at the tertiary N atoms confirm their sp 2 character. The two S=O groups are in syn and gauche conformations with respect to the phosphoryl group. In the crystal, N—H⋯O(=S) and N—H⋯O(=P) hydrogen bonds involving two anions and two cations form a centrosymmetric four-component cluster.

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Section: Data Collectionsupporting

confidence: 86%

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

et al. 2011

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“…The anti orientation is preferred for the C=O versus P=O unit [6,7]. Some researchers have employed the anionic form [P(O)NC(O)] -to obtain compounds with a non-anti orientation [8] and better donority properties [9]. Despite the numerous structures reported in this series [10][11][12][13][14][15][16][17][18][19], there are a few neutral structures with synclinal orientation [2,5,[13][14][15][16][17]19].…”

Section: Introductionmentioning

confidence: 99%

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

et al. 2010

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Different orientations of P(O) versus C(O) in P(O)NHC(O) skeleton have been discussed in two new phosphorus(V)-nitrogen compounds with formula XP(O)Y and XP(O)Z 2 where X = NHC(O)C 6 H 4 (4-F) and Y = NHCH 2 C(CH 3 ) 2 CH 2 NH (1), Z = NHC 6 H 4 (4-CH 3 ) (2). Compound 1 is the first example of an aliphatic diazaphosphorinane with a gauche orientation which has been studied by X-ray crystallography; the P=O bond is in the equatorial position of the ring. Both compounds show n J(F,C) and m J(F,H) coupling constants (n = 1, 2, 3 and 4; m = 3 and 4) and 3 J(P,C) [ 2 J(P,C). Quantum chemical calculations were performed with HF and Density Functional Theory (DFT) methods using 6-31?G(d,p) basis set. A tentative assignment of the observed vibrational bands for these molecules is discussed. Compound 1 shows a deshielded C atom of the carbonyl moiety (in 13 C NMR spectrum) relative to that of 2, which is supported by IR spectroscopy in which the considerably lower C=O frequency is observed for 1. Comparing the X-ray crystallography and IR spectra of 1 and 2 shows that the acyclic compound 2, containing P=O and C=O bonds in an anti position, are involving in a stronger N-HÁÁÁO=P hydrogen bond in crystal network. This leads to a weaker P=O and N C(O)NHP(O) -H bonds and stronger NÁÁÁO interaction. The N amide -H is involved in an intramolecular N-HÁÁÁO hydrogen bond.

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Database analysis of hydrogen bond patterns in phosphoric triamides completed with seven new compounds: a crystallographic and¹⁵N NMR study

et al. 2014

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We present the synthesis and characterization of seven new phosphoric triamides followed by analysis of hydrogen bond patterns of the new compounds as well as the phosphoric triamides found in the Cambridge Structural Database (CSD). The analysis of hydrogen bond patterns updates the previous work (Toghraee, Pourayoubi and Divjakovic in Polyhedron, 2011, 30, 1680) on phosphoric triamides with a CĲO)NHPĲO)ĳN] 2 skeleton, and extends the analysis to other phosphoric triamides i.e. ones without a CO attached to the N of N-PO. For the new phosphoric triamides we also investigated their spectroscopic features ( 31 P, 1 H, 13 C, and 15 N NMR, mass spectroscopy, IR spectroscopy), measured the 1 J( 15 N, 31 P) coupling constants and discussed the effective parameters.

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CyclohexylmethylammoniumN,N′-dicyclohexyl-N,N′-dimethyl-N′′-(2,2,2-trifluoroacetyl)phosphonic triamide)

Abstract: In the salt, C7H16N+·C16H28F3N3O2P−, the P atom shows tetrahedral coordination. Two ion pairs are linked by N—H⋯O hydrogen bonds across a center of inversion. The phosphoryl and carbonyl groups are staggered [O—P—N—C = 64.8 (3)°].

Cited by 3 publications

References 3 publications

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

Database analysis of hydrogen bond patterns in phosphoric triamides completed with seven new compounds: a crystallographic and¹⁵N NMR study

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CyclohexylmethylammoniumN,N′-dicyclohexyl-N,N′-dimethyl-N′′-(2,2,2-trifluoroacetyl)phosphonic triamide)

Abstract: In the salt, C7H16N+·C16H28F3N3O2P−, the P atom shows tetra­hedral coordination. Two ion pairs are linked by N—H⋯O hydrogen bonds across a center of inversion. The phosphoryl and carbonyl groups are staggered [O—P—N—C = 64.8 (3)°].

Cited by 3 publications

References 3 publications

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

Cyclohexyl(methyl)ammonium {bis[cyclohexyl(methyl)amino]phosphoryl}(4-methylphenylsulfonyl)azanide

Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

Database analysis of hydrogen bond patterns in phosphoric triamides completed with seven new compounds: a crystallographic and15N NMR study

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Abstract: In the salt, C7H16N+·C16H28F3N3O2P−, the P atom shows tetrahedral coordination. Two ion pairs are linked by N—H⋯O hydrogen bonds across a center of inversion. The phosphoryl and carbonyl groups are staggered [O—P—N—C = 64.8 (3)°].

Database analysis of hydrogen bond patterns in phosphoric triamides completed with seven new compounds: a crystallographic and¹⁵N NMR study