Oxyanion clusters with antielectrostatic hydrogen bonding (AEHB) in tetraalkylammonium hypodiphosphates

Emami, Marzieh; Ślepokura, Katarzyna; Trzebiatowska, Monika; Noshiranzadeh, Nader; Kinzhybalo, Vasyl

doi:10.1039/c8ce00880a

Cited by 11 publications

(12 citation statements)

References 44 publications

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“…The O•••HO-P hydrogen bonds range from 2.444 to 2.551 Å for Rb 2 [(H 2 P 2 O 6 )(H 4 P 2 O 6 )] and from 2.441 to 2.551 Å for Cs 2 [(H 2 P 2 O 6 )(H 4 P 2 O 6 )] molecule. The P–P distance is 2.175 Å for Rb and 2.182 Å for Cs salts, the P–O bond lengths range from 1.501 to 1.569 Å, and both distances are consistent with the results of other works [ 13 , 16 , 24 , 30 , 31 , 32 ]. Emami et al synthesized organic-inorganic salts of hypodiphosphoric acid tetraalkylammonium cations, which have been characterized by X-ray crystallography, IR spectroscopy, and NMR measurements in the solid state [ 30 ].…”

Section: Hypodiphosphoric Acidsupporting

confidence: 91%

The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review

Nycz¹

2021

Molecules

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The synthesis of hypodiphosphoric acid and its related compounds began in 1877, but no summary of the synthetic efforts has been reported. This review includes published papers related to the molecules containing the >P(=O)-P(=O)< fragment, which notably resembles the structure of the >P(=O)-O-P(=O)< moiety, the essential building block of many important molecules found in nature and in the field of medicinal chemistry. This review covers the strategies related to the synthesis of hypodiphosphoric acid (former name hypophosphoric acid), its ester form, and diphosphine dioxides. Finally, some properties and applications of these structures studied during this period are presented.

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Section: Hypodiphosphoric Acidsupporting

confidence: 91%

The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review

Nycz¹

2021

Molecules

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“…The dehydrated form crystallizes in the same group with the same lattice parameters. In contrast, Kinzhybalo and co-workers (2018) have reported a compound tetra-n-butylammonium hypodiphosphate hydrate [24] in which water is removed from the crystal upon heating, accompanied by a reorganization of the ions present in the crystal.…”

Section: Introductionmentioning

confidence: 96%

Single-Crystal-to-Single-Crystal Transformation and Catalytic Properties of New Hybrid Perhalidometallates

et al. 2021

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Two new organic–inorganic salts of perhalidometallates with protonated organic amine cations have been synthesized and characterized by X-ray diffraction and thermal analysis. (CHBMAH2)ZnBr4·3/2H2O 1 and (CHBMAH2)ZnCl4 4 [(CHBMAH2)2+: 1,3-cyclohexanebis(methylammonium)] were obtained in single-crystal form. The crystal packing in all of the obtained compounds is governed by the formation of various non-covalent intermolecular forces between tetrahalidometallate anions and organic cations, assisted by water molecules in the hydrates. Hirshfeld surface analysis denotes that the most important contributions to the crystal packing are X···H/H···X (X: Cl, Br, I) and H···H interactions. Interestingly, the compound 1,3-cyclohexanebis(methylammonium)tetrachloridozincate (II) dihydrate, (CHBMAH2)ZnCl4·2H2O 2, undergoes thermally-triggered single-crystal-to-single-crystal (SCSC) transformation upon dehydration to produce a supramolecular solid compound, 1,3-cyclohexanebis(methylammonium) tetrachloridozincate (II), (CHBMAH2)ZnCl4 4. The SCSC transformation causes changes in the lattice parameters and a structural rearrangement. Furthermore, the catalytic properties of (CHBMAH2)ZnCl4·2H2O 2 and (CHBMAH2)CdI4·2H2O 3 have been explored in the acetalization process using various uncommon alcohols, beyond methanol or ethanol, for the first time in the literature, with outstanding results, and opening the door to the formation of alternative acetals.

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“…Water removal from a crystal is often accompanied by a conformational change of the ions present ISSN 2053ISSN -2296 # 2019 International Union of Crystallography in the crystal. Emami et al (2018) have reported such a case in tetra-n-butylammonium hypodiphosphate hydrate. Therefore, understanding the nature of the dehydration process, its mechanism and the factors that affect it are needed.…”

Section: Introductionmentioning

confidence: 96%

The dehydration process in the DL-phenylglycinium trifluoromethanesulfonate monohydrate crystal revealed by XRD, vibrational and DSC studies

2019

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Thermal analysis, X-ray diffraction and temperature-dependent IR spectroscopy were used to study the dehydration process of crystalline dl-phenylglycinium trifluoromethanesulfonate monohydrate (PGTFH), C 8 H 10 NO 2 + ÁCF 3 -SO 3 À ÁH 2 O. PGTFH dehydrates in one step centred at 353 K and crystallizes in the monoclinic space group C2/c, whereas the anhydrous compound (PGTF) crystallizes in the triclinic space group P1. The dehydration process in PGTFH is preceded by a weakening of both the noncovalent aromatic-aromatic interactions and the packing contacts. This process is accompanied by the breakage of medium-strength O-HÁ Á ÁO hydrogen bonds between ions inside layers and a reorganization of the ions within the layers. This reorganization results in the formation of two different ion pairs (dl-phenylglycinium trifluoromethanesulfonate) and the formation of a new hydrogen-bond network. The dehydration process does not destroy the nature of the crystal structure. Both crystals, i.e. hydrated and anhydrous, have a layered structure, although the layers of each crystal are arranged somewhat differently.Note: (a) the values given before and after '/' are related to the cooling and heating processes, respectively.

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Oxyanion clusters with antielectrostatic hydrogen bonding (AEHB) in tetraalkylammonium hypodiphosphates

Abstract: Organic–inorganic salts of hypodiphosphoric acid with tetraalkylammonium cations have been synthesized and characterized by X-ray crystallography and IR spectroscopy.

Cited by 11 publications

References 44 publications

The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review

The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review

Single-Crystal-to-Single-Crystal Transformation and Catalytic Properties of New Hybrid Perhalidometallates

The dehydration process in the DL-phenylglycinium trifluoromethanesulfonate monohydrate crystal revealed by XRD, vibrational and DSC studies

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