N,N′-Dicyclohexyl-N′′,N′′-dimethylphosphoric triamide

Sabbaghi, Fahimeh; Pourayoubi, Mehrdad; Ahmadabad, Fatemeh Karimi; Azarkamanzad, Zahra; Valmoozi, Ali Asghar Ebrahimi

doi:10.1107/s160053681100287x

Cited by 8 publications

(9 citation statements)

References 13 publications

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“…Similar cases are observed in compounds containing an (N)P( O)(NH)(NH) moiety [MIFYIJ (Gholivand et al, 2002) and IKASAP (Sabbaghi, Pourayoubi, Karimi Ahmadabad, Azarkamanzad et al, 2011)], where 'one H-atom acceptor and two H-atom donor' sites exist in the molecules (the N atoms are not involved in hydrogen bonding as H-atom acceptors). In [N(CH 3 )(C 6 H 11 )]P(O)(NHC 5 H 4 -2-N) 2 (HIVLII; Gholivand et al, 2008), one of the N-H units is involved in an intramolecular hydrogen bond with one of the pyridine N atoms, the other N-H unit takes part in the P(O)Á Á ÁH-N hydrogen bond.…”

Section: Figuresupporting

confidence: 61%

The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

2012

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In the hydrogen-bond patterns of phenyl bis(2-chlorobenzylamido)phosphinate, C(20)H(19)Cl(2)N(2)O(2)P, (I), and N,N'-bis(2-chlorobenzyl)-N''-(2,2,2-trifluoroacetyl)phosphoric triamide, C(16)H(15)Cl(2)F(3)N(3)O(2)P, (II), the O atoms of the related phosphoryl groups act as double H-atom acceptors, so that the P=O···(H-N)(2) hydrogen bond in (I) and the P=O···(H-N(amide))(2) and C=O···H-N(C(O)NHP(O)) hydrogen bonds in (II) are responsible for the aggregation of the molecules in the crystal packing. The presence of a double H-atom acceptor centre is a result of the involvement of a greater number of H-atom donor sites with a smaller number of H-atom acceptor sites in the hydrogen-bonding interactions. This article also reviews structures having a P(O)NH group, with the aim of finding similar three-centre hydrogen bonds in the packing of phosphoramidate compounds. This analysis shows that the factors affecting the preference of the above-mentioned O atom to act as a double H-atom acceptor are: (i) a higher number of H-atom donor sites relative to H-atom acceptor centres in molecules with P(=O)(NH)(3), (N)P(=O)(NH)(2), C(=O)NHP(=O)(NH)(2) and (NH)(2)P(=O)OP(=O)(NH)(2) groups, and (ii) the remarkable H-atom acceptability of this atom relative to the other acceptor centre(s) in molecules containing an OP(=O)(NH)(2) group, with the explanation that the N atom bound to the P atom in almost all of the structures found does not take part in hydrogen bonding as an acceptor. Moreover, the differences in the H-atom acceptability of the phosphoryl O atom relative to the O atom of the alkoxy or phenoxy groups in amidophosphoric acid esters may be illustrated by considering the molecular packing of compounds having (O)(2)P(=O)(NH) and (O)P(=O)(NH)(N)groups, in which the unique N-H unit in the above-mentioned molecules almost always selects the phosphoryl O atom as a partner in forming hydrogen-bond interactions. The P atoms in (I) and (II) are in tetrahedral coordination environments, and the phosphoryl and carbonyl groups in (II) are anti with respect to each other (the P and C groups are separated by one N atom). In the crystal structures of (I) and (II), adjacent molecules are linked via the above-mentioned hydrogen bonds into a linear arrangement parallel to [100] in both cases, in (I) by forming R(2)(2)(8) rings and in (II) through a combination of R(2)(2)(10) and R(2)(1)(6) rings.

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Section: Figuresupporting

confidence: 61%

The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

2012

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“…1b) (MIFYIJ; Gholivand et al, 2002); (iii) formed via an R 2 2 (8) ring ( Fig. 1c) (IKASAP; Sabbaghi et al, 2011) [see Bernstein et al (1995) for nomenclature of hydrogen-bond motifs]. In the two latter cases, with POÁ Á Á(H-N)(H-N) groups, the phosphoryl O atom acts as a double hydrogen-bond acceptor.…”

mentioning

confidence: 99%

Two newXP(O)[NHC(CH₃)₃]₂phosphoramidates, withX= (CH₃)₂N and [(CH₃)₃CNH]₂P(O)(O)

Pourayoubi¹,

Tarahhomi²,

Ahmadabad³

et al. 2012

Acta Crystallogr C

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In N,N'-di-tert-butyl-N'',N''-dimethylphosphoric triamide, C(10)H(26)N(3)OP, (I), and N,N',N'',N'''-tetra-tert-butyl[oxybis(phosphonic diamide), [corrected] C(16)H(40)N(4)O(3)P(2), (II), the extended structures are mediated by P(O)...(H-N)(2) interactions. The asymmetric unit of (I) consists of six independent molecules which aggregate through P(O)...(H-N)(2) hydrogen bonds, giving R(2)(1)(6) loops and forming two independent chains parallel to the a axis. Of the 12 independent tert-butyl groups, five are disordered over two different positions with occupancies ranging from 1/6 to 5/6. In the structure of (II), the asymmetric unit contains one molecule. P(O)...(H-N)(2) hydrogen bonds give S(6) and R(2)(2)(8) rings, and the molecules form extended chains parallel to the c axis. The structures of (I) and (II), along with similar structures having (N)P(O)(NH)(2) and (NH)(2)P(O)(O)P(O)(NH)(2) skeletons extracted from the Cambridge Structural Database, are used to compare hydrogen-bond patterns in these families of phosphoramidates. The strengths of P(O)[...H-N](x) (x = 1, 2 or 3) hydrogen bonds are also analysed, using these compounds and previously reported structures with (N)(2)P(O)(NH) and P(O)(NH)(3) fragments.

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“…In compounds having an (N)P(O)(NH) 2 skeleton, three different linear arrangements were observed: a) through P(O)···H-N hydrogen bonds in which one N-H unit doesn't cooperate in H-bonding (NUVROL [107], Scheme 27 and HIVLII [67], Scheme 28), b) through R 2 1 (6) (in [(CH 3 ) 2 [62] and the compound with refcode IKASAP [47], Scheme 29 (bottom)), two latter cases via P(O)···(H-N)(H-N) grouping in which the phosphoryl oxygen atom acts as a double-H acceptor.…”

Section: General Features Of Phosphoramidate Compoundsmentioning

confidence: 99%

“…Scheme 29. Refcodes MIFYIJ (top) [114] and IKASAP (bottom) [47] www.intechopen.com Scheme 30. Refcodes BIXFOE (top) [115] and GOMDOB (bottom) [116] …”

Section: General Features Of Phosphoramidate Compoundsmentioning

confidence: 99%

“…The preparation of some compounds containing the P-Cl bonds, such as 4-CH 3 C 6 H 4 OP(O)Cl 2 and [(CH 3 ) 2 N]P(O)Cl 2 , were performed through the reaction between corresponding phenol derivatives or amine hydrochloride salts [for example para-cresol or dimethylamine hydrochloride salt for the mentioned phosphorus-chlorine compounds] with an excess amount of POCl 3 and then the removal of the remaining POCl 3 in a reduced pressure [32,47].…”

Section: Synthesis and Purification Of Phosphoramidates And Phosphorimentioning

confidence: 99%

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Phosphoramidates: Molecular Packing and Hydrogen Bond Strength in Compounds Having a P(O)(N)n(O)3-n (n = 1, 2, 3) Skeleton

Pourayoubi¹,

Sabbaghi²,

Divjaković³

et al. 2012

Advances in Crystallization Processes

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N,N′-Dicyclohexyl-N′′,N′′-dimethylphosphoric triamide

Cited by 8 publications

References 13 publications

The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

Two newXP(O)[NHC(CH₃)₃]₂phosphoramidates, withX= (CH₃)₂N and [(CH₃)₃CNH]₂P(O)(O)

Phosphoramidates: Molecular Packing and Hydrogen Bond Strength in Compounds Having a P(O)(N)n(O)3-n (n = 1, 2, 3) Skeleton

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N,N′-Dicyclohexyl-N′′,N′′-dimethylphosphoric triamide

Cited by 8 publications

References 13 publications

The double H-atom acceptability of the P=O group in newXP(O)(NHCH2C6H4-2-Cl)2phosphoramidates [X= C6H5O– and CF3C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

The double H-atom acceptability of the P=O group in newXP(O)(NHCH2C6H4-2-Cl)2phosphoramidates [X= C6H5O– and CF3C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

Two newXP(O)[NHC(CH3)3]2phosphoramidates, withX= (CH3)2N and [(CH3)3CNH]2P(O)(O)

Phosphoramidates: Molecular Packing and Hydrogen Bond Strength in Compounds Having a P(O)(N)n(O)3-n (n = 1, 2, 3) Skeleton

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The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

The double H-atom acceptability of the P=O group in newXP(O)(NHCH₂C₆H₄-2-Cl)₂phosphoramidates [X= C₆H₅O– and CF₃C(O)NH–]: a database analysis of compounds having a P(O)(NHR) group

Two newXP(O)[NHC(CH₃)₃]₂phosphoramidates, withX= (CH₃)₂N and [(CH₃)₃CNH]₂P(O)(O)