Structure of iminobis(methylphosphonic) and cyclohexyliminobis(methylphosphonic) acids

Shkol'nikova, L. M.; Polyanchuk, G. V.; Dyatlova, N. M.; Medved, T. Ya.; Goryunova, I. B.; Кабачник, М. И.

doi:10.1007/bf01142780

Cited by 3 publications

(4 citation statements)

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“…Table 6 summarises selected bond distances and angles. Similarly, as with other iminodimethylenediphosphonates described previously (1, 3 and 5), 23,24 2 occurs in a zwitterionic form. The hydrogen atoms H(1), H( 5) and H (6) are located near to O(1), O (5) and O( 6) oxygens (see Fig.…”

Section: Crystal Structure Of Compoundsupporting

confidence: 79%

Interactions of zinc(II), magnesium(II) and calcium(II) with iminodimethylenediphosphonic acids in aqueous solutions †

Matczak-Jon¹,

Kurzak²,

Kamecka³

et al. 1999

J. Chem. Soc., Dalton Trans.

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N-Substituted iminodimethylenediphosphonic acids exhibited high complexation efficiency towards zinc(), magnesium() and calcium() ions. This results from both dinegatively charged phosphonate groups as well as the imino-nitrogen present in their structure. A significant preference for an equimolar stoichiometry and a formation of tridentate bonded species has been demonstrated in these systems. The only exception is the N-tetrahydrofurylmethyliminodimethylenediphosphonic acid with a tetrahydrofuryl moiety placed in the sterically favoured position that allows its oxygen atom to be an effective metal binding site. Iminodimethylenediphosphonic and N-methyliminodimethylenediphosphonic acids behave quite differently upon zinc() complexation forming presumably layered two-dimensional polymeric species. These species disappear upon dilution. The crystal structure of N-methyliminodimethylenediphosphonic acid has also been determined. A unique 3-D arrangement of this compound with a tetramer as a basic building unit has been indicated.

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Section: Crystal Structure Of Compoundsupporting

confidence: 79%

Interactions of zinc(II), magnesium(II) and calcium(II) with iminodimethylenediphosphonic acids in aqueous solutions †

Matczak-Jon¹,

Kurzak²,

Kamecka³

et al. 1999

J. Chem. Soc., Dalton Trans.

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“…Recently, another very short OH···O distance in BTP with 4-(dimethylamino)pyridine amounting to 2.431(2) Å also has been reported 4b. In the dimer structure of benzene-1,3,5-tris(methylphophonic acid), two similar OH···O bonds of 2.442 and 2.484 Å were found with negative charge assisted hydrogen bonding, as shown in Figure . The trianionic moieties {1,3,5-[(OH)PO 2 ] 3 -C 6 H 3 } 3- assembled with two hydrogen bonds along the b axis to form staircase-type layers as a result of the planar stacking of the benzene rings (Figure a).…”

Section: Resultsmentioning

confidence: 77%

Crystal-Engineered Three-Dimensional Hydrogen-Bonding Networks Built with 1,3,5-Benzenetri(phosphonic acid) and Bipyridine Synthons

Kong

Clearfield

Zoń

2005

Crystal Growth & Design

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The phosphonic acid 1,3,5-benzenetri(phosphonic acid) (BTP; 1,3,5-[(OH) 2 PO] 3 -C 6 H 3 ) can act as both a hydrogen bond donor and acceptor. BTP was reacted with two organic bases, 2,2′-bipyridine and 4,4′-bipyridine, in a 1:1 molar ratio. The bis-deprotonation and tris-deprotonation trigger the formation of self-complementary 3D hydrogen bonding architectures. Layers of the 2,2′-bipyridine compound are formed through hydrogen bonding of the phosphonic acid groups existing in the dianionic motifThe ratio of BTP to 2,2′-bipyridine is 1:1.5, with two of the phosphonic acid protons being transferred to the nitrogen atoms, leaving a negatively charged oxygen and a proton on each of the phosphonic acid groups. Discrete dimers are formed by three very short PO-H‚‚‚O-P type hydrogen bonds (2.45-2.48 Å) and one short PO-H‚‚‚OdP hydrogen bond at 2.56 Å interconnecting all dimers into extended layers in the bc plane. The protonated bipyridyls penetrated into the layers by formation of two NH + ‚‚‚O-P hydrogen bonds (2.72, 3.14 Å) to complete the 3D network. The compound with 4,4′-bipyridine is triclinic P1 h, in which the ratio of BTP to bipyridine is 1:1. Each amino nitrogen atom is protonated, leaving each phosphonic acid group negatively charged. One additional positive charge is provided by a hydronium ion. The BTP molecules align in hydrogen-bonded staircase chains along the b axis, in which the molecules are bonded together by double hydrogen bonds: P-O -‚‚‚HO-P. The staircases are then interwoven into each other by the NH + ‚‚‚O-P hydrogen bonds between the pyridyl and the phosphonic acid groups.

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“…The crystal structure of the ligand has been reported in triclinic, space group P-1, with the cell parameters of a ) 5.575(2), b ) 8.003-(2), c ) 8.643(2) Å, R ) 110.10(2), β ) 88.68(2), and γ ) 100.16(2)°with Z ) 2 and the CCDC code DOZLAF. 10 The title ligand crystallized in our experiment is orthorhombic, P2 1 2 1 2 1 space group with Z ) 4 and different packing parameters. Table 1 gives the crystal data information, and the corresponding bond lengths and bond angles of all four compounds are deposited in Supporting Information.…”

Section: Resultsmentioning

confidence: 96%

“…Crystal Structure of NDP, 1. The crystal structure of the ligand has been reported in triclinic, space group P -1, with the cell parameters of a = 5.575(2), b = 8.003(2), c = 8.643(2) Å, α = 110.10(2), β = 88.68(2), and γ = 100.16(2)° with Z = 2 and the CCDC code DOZLAF …”

Section: Resultsmentioning

confidence: 99%

Crystal Engineered Acid−Base Complexes with 2D and 3D Hydrogen Bonding Systems Using a Bisphosphonic Acid as the Building Block

Kong

McBee

Clearfield

2004

Crystal Growth & Design

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The phosphonic acid iminobis(methylene phosphonic acid), NDP, [NH 2 (CH 2 PO 3 H) 2 ][H 3 O], exists as a zwitterion and can act as both a hydrogen bond donor and acceptor. NDP synthon was reacted with three organic bases, 2,2′-bipyridine, 4,4′-trimethylene-dipyridine, and a hexaazamacrocyclic crown ether, to construct highly stable hydrogen bonded structures. The 2,2′-bipyridine complex 2 is layered, the layers being formed through hydrogen bonding of the phosphonic acid groups. The layers are largely formed by strong PO-H‚‚‚ -O-P type hydrogen bonds (2.49-2.62 Å) with the protonated bipyridyls held between the layers by strong NH + ‚‚‚O-P hydrogen bonds. In complex 3, each amino-nitrogen atom is protonated leaving each phosphonic acid group negatively charged. The NDP molecules align in hydrogen bonded rows in which the molecules are bonded together by quadruple hydrogen bonds: two P-O -‚‚‚HO-P and two NH 2 + ‚‚‚O-P. The rows are then connected to each other by the NH 2 + ‚‚‚O-P hydrogen bonds between the pyridyl and the phosphonic acid groups. In compound 4, the azacrown ether ring encloses two NDP molecules with four such entities arranged in the unit cell according to the P2 1 /n symmetry. There are 14 water molecules per ring filling the voids between the rings creating a three-dimensional hydrogen bonding network.

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Structure of iminobis(methylphosphonic) and cyclohexyliminobis(methylphosphonic) acids

Cited by 3 publications

References 0 publications

Interactions of zinc(II), magnesium(II) and calcium(II) with iminodimethylenediphosphonic acids in aqueous solutions †

Interactions of zinc(II), magnesium(II) and calcium(II) with iminodimethylenediphosphonic acids in aqueous solutions †

Crystal-Engineered Three-Dimensional Hydrogen-Bonding Networks Built with 1,3,5-Benzenetri(phosphonic acid) and Bipyridine Synthons

Crystal Engineered Acid−Base Complexes with 2D and 3D Hydrogen Bonding Systems Using a Bisphosphonic Acid as the Building Block

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