Dihydrogen phosphate mediated supramolecular frameworks in 2- and 4-chloroanilinium dihydrogen phosphate salts

Balamurugan, P.; Jagan, R.; Sivakumar, K.

doi:10.1107/s0108270110001940

Cited by 15 publications

(8 citation statements)

References 30 publications

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“…1). The bond distances and angles of the cation are comparable with the related 4-chloroanilinium structures (Balamurugan et al, 2010;Ploug-Sørenson & Andersen, 1985;Rahmouni et al, 2010;Smith et al, 2005Smith et al, , 2007Smith et al, , 2009. The planes of the cation and the hydrogen maleate anion are oriented at an angle of 15.6 (1)° to each other.…”

Section: Methodssupporting

confidence: 68%

4-Chloroanilinium 3-carboxyprop-2-enoate

Anitha¹,

Athimoolam²,

Bahadur³

et al. 2012

Acta Cryst E

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In the title compound, C6H7ClN+·C4H3O4 −, the cations and anions lie on mirror planes and hence only half of the molecules are present in the asymmeric unit. The 4-chloroanilinium cation and hydrogen maleate anion in the asymmetric unit are each planar and are oriented at an angle of 15.6 (1)° to one another and perpendicular to the b axis. A characterestic intramolecular O—H⋯O hydrogen bond, forming an S(7) motif, is observed in the maleate anion. In the crystal, the cations and anions are linked by N—H⋯O hydrogen bonds, forming layers in the ab plane. The aromatic rings of the cations are sandwiched between hydrogen-bonded chains and rings formed through the amine group of the cation and maleate anions, leading to alternate hydrophobic (z = 0 or 1) and hydrophilic layers (z = 1/2) along the c axis.

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Section: Methodssupporting

confidence: 68%

4-Chloroanilinium 3-carboxyprop-2-enoate

Anitha¹,

Athimoolam²,

Bahadur³

et al. 2012

Acta Cryst E

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“…2). The building blocks of the inorganic layer are deformed H 2 PO 4 tetrahedra with two narrow groups of O-P-O angles (median values $105 and $111 ) and with the P-O bond lengths falling into two groups (Table 1); the P-O(H) bonds are, as expected, longer than the other presumably P O bonds (Blessing, 1986;Mahmoudkhani & Langer, 2002;Demir et al, 2003;Smrčok et al, 2009;Balamurugan et al, 2010;Kaman et al, 2011;Marouani et al, 2011). Examination of the geometry of the anilinium cations forming the organic layers shows that the values of the bond distances, bond angles and torsion angles have expected values (Elmokhtar et al, 1995).…”

Section: Commentmentioning

confidence: 60%

Anilinium dihydrogen phosphate

Kaman

Smrčok²,

Gyepes³

et al. 2012

Acta Crystallogr C

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The triclinic structure of the title compound, C(6)H(8)N(+)·H(2)PO(4)(-), with three symmetry-independent structural units (Z' = 3), is formed of separate organic and inorganic layers alternating along the b axis. The building blocks of the inorganic layer are deformed H(2)PO(4) tetrahedra assembled into infinite ladders by short and hence strong hydrogen bonds. The anilinium cations forming the organic layer are not hydrogen bonded to one another, but they are anchored by four N-H···O crosslinks between the dihydrogen phosphate chains of adjacent ladders. Two H atoms of each -NH(3) group then form one normal and one bifurcated N-H···O hydrogen bond to the P=O oxygens of two tetrahedra of one chain, while the third H atom is hydrogen bonded to the nearest O atom of an adjacent chain belonging to another dihydrogen phosphate ladder.

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“…This finds valid applications in gas or chemical storage, sensors, catalysis and ion exchange (Tranchemontagne et al, 2009;Allendorf et al, 2009). As a continuation of research on the supramolecular architectures of inorganic oxy-acid-based salts (Balamurugan et al, 2010), we report here the crystal structures and supramolecular frameworks in two dihydrogen phosphate salts, namely 1-methylpiperazine-1,4-diium bis(dihydrogen phos- ISSN 2053ISSN -2296 # 2015 International Union of Crystallography phate), (I), and 2-(pyridin-2-yl)pyridinium dihydrogen phosphate-orthophosphoric acid (1/1), (II).…”

Section: Introductionmentioning

confidence: 94%

A dihydrogen phosphate anionic network as a host lattice for cations in 1-methylpiperazine-1,4-diium bis(dihydrogen phosphate) and 2-(pyridin-2-yl)pyridinium dihydrogen phosphate–orthophosphoric acid (1/1)

2015

Self Cite

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In the salt 1-methylpiperazine-1,4-diium bis(dihydrogen phosphate), C5H13N2(2+)·2H2PO4(-), (I), and the solvated salt 2-(pyridin-2-yl)pyridinium dihydrogen phosphate-orthophosphoric acid (1/1), C10H9N2(+)·H2PO4(-)·H3PO4, (II), the formation of O-H...O and N-H...O hydrogen bonds between the dihydrogen phosphate (H2PO4(-)) anions and the cations constructs a three- and two-dimensional anionic-cationic network, respectively. In (I), the self-assembly of H2PO4(-) anions forms a two-dimensional pseudo-honeycomb-like supramolecular architecture along the (010) plane. 1-Methylpiperazine-1,4-diium cations are trapped between the (010) anionic layers through three N-H...O hydrogen bonds. In solvated salt (II), the self-assembly of H2PO4(-) anions forms a two-dimensional supramolecular architecture with open channels projecting along the [001] direction. The 2-(pyridin-2-yl)pyridinium cations are trapped between the open channels by N-H...O and C-H...O hydrogen bonds. From a study of previously reported structures, dihydrogen phosphate anions show a supramolecular flexibility depending on the nature of the cations. The dihydrogen phosphate anion may be suitable for the design of the host lattice for host-guest supramolecular systems.

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Dihydrogen phosphate mediated supramolecular frameworks in 2- and 4-chloroanilinium dihydrogen phosphate salts

Cited by 15 publications

References 30 publications

4-Chloroanilinium 3-carboxyprop-2-enoate

4-Chloroanilinium 3-carboxyprop-2-enoate

Anilinium dihydrogen phosphate

A dihydrogen phosphate anionic network as a host lattice for cations in 1-methylpiperazine-1,4-diium bis(dihydrogen phosphate) and 2-(pyridin-2-yl)pyridinium dihydrogen phosphate–orthophosphoric acid (1/1)

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