Dicyclohexylammonium hydrogen phenylphosphonate

Abstract

In the title salt, [(C6H11)2NH2]+·[C6H5PO2(OH)]−, the anion is monodeprotonated and acts as both a hydrogen-bond donor and acceptor. The anions are linked by pairs of O—H⋯O inter­actions, forming inversion dimers with R 2 2(8) ring motifs. These dimers are bridged by two dicyclo­hexyl­aminium cations via pairs of N—H⋯O hydrogen bonds, giving R 4 4(12) ring motifs, forming chains propagating along [010]. The chains are bridged by C—H⋯O inter­actions, forming a two-dimensional network lying parallel to (101).

Crystal Structures of Two Phosphonate Salts: Monocyclohexylammonium Hydrogen Phosphonate and Monocyclohexylammonium Phenyl Phosphonate

“…The hydrogen phosphonate anion with P-O distances ranging from 1.505 (2) Å to 1.579 (2) Å and angles comprised between 105.04 (7) and 116.65 (9)° describes a distorted tetrahedral geometry and are in the range of those previously reported [18][19][20]. The O atoms of the longer P-O bond are both involved in a very strong hydrogen bonding interaction [9,10,21], the significantly longer one being involved in a second strong hydrogen bond. The shortest P-O bond is that whose O atom act as acceptor of two symmetric hydrogen bonds.…”

“…To date, hundreds and hundreds structures of monocyclohexyl ammonium have been deposited in the CSD. The Dakar group focusing in phosphonate characterization has reported several works [8][9][10]. Recently, we published the crystalline structures of two triorganotin phosphonate polymers among with the first PH2bridged triorganotin phosphonate polymer [11].…”

Dicyclohexylammonium O,O’-Diphenyl Phosphate, [(C6H11)2NH2][(C6H5O)2P(O)(O)]: Spectroscopic Study, Crystal Structure, and Hirshfeld Surface Analysis

“…In the anion, the phosphorus atom has a distorted tetrahedral In the cation, the cyclohexyl rings adopt a chair conformation, and the NH 2 unit is situated in the equatorial position with respect to the rings. The large C-N-C angle, of 118.1(2) • , is a result of the steric bulk of the cyclohexyl rings, as has been also observed in the structures with the same cation, typically in [(C 6 H 11 ) 2 NH 2 ][C 6 H 5 PO 2 (OH)] (with CSD refcode ZARGOQ and the C-N-C angle of 118.80(10) • ) [9].…”

“…CSD study has been carried out to understand the similarities and conformational changes of the title compound. Fourteen structures (CSD REFCODES: CADGUJ [11], EFUMEX [12], GAGQOV [13], HAXRAZ [14], JOXMAK [15], LOKGUN [16], OBOTOQ [17], TEDFIR [18], WILKOR [19], YIWXOR [20], ZALTEL [21], ZALTIP [21], ZARGOQ [9], and ZETHIP [2]) containing the cation "dicyclohexylammonium" moiety were retrieved from the CSD. The bond lengths (Supplementary Table S1, Figure 5A), selected bond angles (Supplementary Table S2, Figure 5B), and selected torsion angles C14-C13-N1-C19 and C24-C19-N1-C13 (Supplementary Table S3, Figure 6) of the cation component are compared with the literature.…”

Pentafluorophenylphosphonic Acid as a New Building Block for Molecular Crystal Fabrication

“…Owing to this structural peculiarity, metal arylphosphonates are amenable to intercalation type reactions, exhibit ion exchange properties, can be used as heterogeneous acid catalysts, and show good prospects as proton conductors . Yet, despite the large body of literature available on these latter materials, only a limited number of papers have been published concerning the use of phenylphosphonic acid in crystal engineering studies. − Even more surprisingly, just one report could be found concerning the crystallographic characterization of fluorinated arylphosphonic acids, in sharp contrast with the fact that fluorine-containing molecules are now emerging as important building blocks for molecular assembly fabrication . We wish to continue this theme here and report on the synthesis of molecular crystals derived from pentafluorophenylphosphonic acid ( 4 ) (Scheme ).…”