Protonated Trithiocarbonic Acid − Synthesis, Spectroscopic Characterization and the Crystal Structure of C(SH)3+AsF6−

Minkwitz, R.; Neikes, Frank; Lohmann, Ulrike

doi:10.1002/1099-0682(20021)2002:1<27::aid-ejic27>3.0.co;2-o

Cited by 20 publications

(19 citation statements)

References 27 publications

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“…The expected octahedral geometry of the hexafluoridoarsenate is slightly distorted by a hydrogen bond (O1‐(H1)⋅⋅⋅F2). All As−F bond lengths are with 1.705(2) Å to 1.775(2) Å in a typical range for an [AsF 6 ] − anion …”

Section: Resultssupporting

confidence: 66%

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Investigations on Squaric Acid in Superacidic Media

Schickinger

Cibu

Zischka

et al. 2018

Chemistry A European J

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The syntheses of [OC(COX) ][MF ] and [(COX) ][MF ] ⋅2 HF were carried out in superacidic media XF/MF (M=As, Sb; X=H, D). The degree of protonation is highly dependent on the stoichiometric ratio of the Lewis acid with regard to squaric acid. The salts of diprotonated squaric acid were characterized by Raman spectroscopy and, in the case of [(COH) ][MF ] ⋅2 HF (M=As, Sb), by single-crystal X-ray structure analyses. [(COH) ][AsF ] crystallizes in the monoclinic space group P2 /n with two formula units per unit cell. Analysis of the vibrational spectra was achieved with the support of quantum chemical calculations of the cation [(COH) ] ⋅4 HF on the PBE1PBE/6-311G++(3df,3pd) level of theory. Furthermore, a salt of monoprotonated squaric acid, [OC(COH) ][AsF ], was characterized by a single-crystal X-ray structure analysis. It crystallizes in the monoclinic space group P2 /n with four formula units per unit cell. The protonation of squaric acid leads to a change of the carbon skeleton, which is discussed for the entire series, starting with the dianion of squaric acid and ending with the tetrahydroxy dication.

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Section: Resultssupporting

confidence: 66%

“…All As−F bonds are, with bond distances between 1.703(1) Å and 1.750(1) Å, in the typical range for an [AsF 6 ] − anion. The ideal octahedral geometry of the [AsF 6 ] − anion is slightly distorted, due to the As1−F4 (1.750(1) Å) and A1s−F2 (1.735(1) Å) bonds being involved in hydrogen bonding …”

Section: Resultsmentioning

confidence: 99%

Investigations on Squaric Acid in Superacidic Media

Schickinger

Cibu

Zischka

et al. 2018

Chemistry A European J

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“…The As‐F bond lengths of the [AsF 6 ] − anion are range from 1.710(3) Å to 1.750(3) Å. These values are typical for an [AsF 6 ] − anion . The anions form slightly distorted octahedrons.…”

Section: Resultsmentioning

confidence: 99%

The Tetrahydroxydicarbenium Cation [(HO)₂CC(OH)₂]²⁺: Synthesis and Structure

et al. 2018

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Oxalic acid forms in superacidic solutions HF/MF5 (M = As, Sb) its corresponding mono‐ and diprotonated salts [HOOCC(OH)2][MF6] and [(HO)2CC(OH)2][MF6]2 (M = As, Sb). The number of protonations is strongly dependent on the stoichiometric ratio of the Lewis acid with regard to oxalic acid. Mono‐ and diprotonated salts were characterized by vibrational spectroscopy and in the case of [HOOCC(OH)2][AsF6] (1) and [(HO)2CC(OH)2][SbF6]2 (4) by a single‐crystal X‐ray structure analysis. The salts crystallize in the monoclinic space groups P21/c and P21/n with eight, respectively four, formula units per unit cell. The vibrational spectra were compared to quantum chemical calculations of the cations [HOOCC(OH)2]+ and [(OH)2CC(OH)2]2+⋅4HF. In addition to this, an MEP analysis together with the NPA charges of [(OH)2CC(OH)2]2+, [(OH)2CC(OH)2]2+⋅6HF and oxalic acid were calculated to locate the positive charge. The protonation of oxalic acid does not lead to a remarkable change of the C‐C bond length, which is discussed for the entire series of the oxalic skeleton, starting with the dianion and ending with the tetrahydroxy dication.

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“…These values are typical for an [AsF 6 ] -anion. [8] The anions form slightly distorted octahedrons. The As-F bonds, which are involved in hydrogen bonds (As1-F6, As1-F2, and As2-F7, As2-F8, and As2-F12) are slightly longer than the other As-F bonds.…”

Section: Crystal Structure Of [H 2 C(cnh) 2 ][Asf 6 ]mentioning

confidence: 99%

Protonation of Malononitrile in Superacidic Solutions

Schickinger

Morgenstern

Stierstorfer

et al. 2017

Zeitschrift anorg allge chemie

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Abstract. Malononitrile reacts in superacidic solutions HF/MF 5 (M = As, Sb) with formation of the corresponding salts [H 2 C(CNX) 2 ][MF 6 ] 2 (M = As, Sb; X = H, D). The occurrence of double protonation is strongly dependent on the stoichiometric ratio of the Lewis acid with regard to malononitrile. Deuterated species were obtained by replacing hydrogen fluoride with deuterium fluoride. The double protonated salts

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Protonated Trithiocarbonic Acid − Synthesis, Spectroscopic Characterization and the Crystal Structure of C(SH)3+AsF6−

Cited by 20 publications

References 27 publications

Investigations on Squaric Acid in Superacidic Media

Investigations on Squaric Acid in Superacidic Media

The Tetrahydroxydicarbenium Cation [(HO)₂CC(OH)₂]²⁺: Synthesis and Structure

Protonation of Malononitrile in Superacidic Solutions

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Protonated Trithiocarbonic Acid − Synthesis, Spectroscopic Characterization and the Crystal Structure of C(SH)3+AsF6−

Cited by 20 publications

References 27 publications

Investigations on Squaric Acid in Superacidic Media

Investigations on Squaric Acid in Superacidic Media

The Tetrahydroxydicarbenium Cation [(HO)2CC(OH)2]2+: Synthesis and Structure

Protonation of Malononitrile in Superacidic Solutions

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The Tetrahydroxydicarbenium Cation [(HO)₂CC(OH)₂]²⁺: Synthesis and Structure