Synthese und Kristallstruktur von N‐Formylformamidinium‐hexachloroantimonat

Allenstein, E.; Keller, K.; Hausen, H.‐D.; Weidlein, Johann

doi:10.1002/zaac.19875541125

Cited by 4 publications

(5 citation statements)

References 16 publications

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“…The Mo(1)−O(1) [1.647(6) Å] and Mo(1)−O(2) [2.386(5) Å] interactions are considerably different: the former has double-bond character, whereas the latter is a single-coordination bond. The [MeC(O)N(Ph)C(Me)NHPh] + ligand displays bonding parameters similar to those found in the previously described acylamidinium salts [HC(O)NHCHNH 2 ][SbCl 6 ] and [ t BuC(O)NHC( t Bu)NH 2 ] 2 [S 2 O 7 ] . In particular, both C(1)−O(2) [1.222(10) Å] and C(2)−N(2) [1.292(11) Å] interactions are almost pure double bonds, while the O(2)−C(1)−N(1)−C(2)−N(2) core is nearly planar [mean deviation from the least-squares plane 0.0202 Å].…”

supporting

confidence: 66%

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

et al. 2011

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supporting

confidence: 66%

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

et al. 2011

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“…Overall, the delocalized C-N distances average to 1.310 (11) A ˚. Entry FUMGUP (Allenstein et al, 1987) is the aldehyde derivative, where the delocalized C N distances differ slightly, by 0.02 A ˚. We did not find any examples of terminal formamidinium groups attached to nitrogen heterocycles, as in the present structures.…”

Section: Figuresupporting

confidence: 50%

“…Here, however, the spectrum in the N-H stretch region is more complex, with multiple bands below the prominent band at 3453 cm À 1 . Allenstein et al (1987) include a review of the IR data for their aldehyde complex, with N-H stretches at 3342 and 3240 cm À 1 , and a band at 1695 cm À 1 for the asymmetric N-C N stretch; further assignments are given in more detail than covered in the present paper.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structures of two formamidinium hexafluoridophosphate salts, one with batch-dependent disorder

Neary,

Corfield,

Parkin

et al. 2024

Acta Cryst E

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Syntheses of the acyclic amidinium salts, morpholinoformamidinium hexafluoridophosphate [OC4H8N—CH=NH2]PF6 or C5H11N2O+·PF6 −, 1, and pyrrolidinoformamidinium hexafluoridophosphate [C4H8N—CH= NH2]PF6 or C5H11N2 +·PF6 −, 2, were carried out by heating either morpholine or pyrrolidine with triethyl orthoformate and ammonium hexafluoridophosphate. Crystals of 1 obtained directly from the reaction mixture contain one cation and one anion in the asymmetric unit. The structure involves cations linked in chains parallel to the b axis by N—H...O hydrogen bonds in space group Pbca, with glide-related chains pointing in opposite directions. Crystals of 1 obtained by recrystallization from ethanol, however, showed a similar unit cell and the same basic structure, but unexpectedly, there was positional disorder [occupancy ratio 0.639 (4):0.361 (4)] in one of the cation chains, which lowered the crystal symmetry to the non-centrosymmetric space group Pca21 , with two cations and anions in the asymmetric unit. In the pyrrolidino compound, 2, cations and anions are ordered and are stacked separately, with zigzag N—H...F hydrogen-bonding between stacks, forming ribbons parallel to (101), extended along the b-axis direction. Slight differences in the delocalized C=N distances between the two cations may reflect the inductive effect of the oxygen atom in the morpholino compound.

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“…To our knowledge, the anion of N-imino-methyl-formamide, Imf Ϫ , has never been used as a ligand before. The respective cation, H 2 Imf ϩ , has been observed in the salt H 2 Imf[SbCl 6 ] [14].…”

Section: Introductionmentioning

confidence: 99%

“…The crystal structure [monoclinic, P2 1 /c (no. 14), a ϭ 499.6(2), b ϭ 1051.2(4), c ϭ 711.1(3) pm, β ϭ 117.55(1)°, Z ϭ 2, R 1 for 890 reflections with I 0 >2σ(I 0 ): 0.0369] contains linear centrosymmetric Hg(Imf) 2…”

mentioning

confidence: 99%

Mercuric Bis(N‐imino‐methyl‐formamidate), Hg(Imf)₂

Nockemann

Pantenburg

Meyer

2008

Zeitschrift anorg allge chemie

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Single crystals of mercuric bis(N-imino-methyl-formamidate), Hg(Imf) 2 , were obtained from aqueous solutions of 1,2,4triazole and Hg(NO 3 ) 2 · 2H 2 O. The crystal structure [monoclinic, P2 1 /c (no. 14), a ϭ 499.6(2), b ϭ 1051.2(4), c ϭ 711.1(3) pm, β ϭ 117.55(1)°, Z ϭ 2, R 1 for 890 reflections with I 0 >2σ(I 0 ): 0.0369] contains linear centrosymmetric Hg(Imf) 2 molecules with HgϪN Divalent mercury as a heavy closed-shell d 10 cation has a remarkably high affinity towards N-donor ligands [1]. Relativistic effects are responsible for the preference of the characteristic coordination number 2 (over 4 or 6) although a large variety of effective coordination numbers [2] are well known. The characteristic coordination number 2 is associated with short HgϪN distances of highly covalent bonding character whenever the free electron pair of the N-donor ligand is well available. This is certainly the case in the zero-to three-dimensional cationic complexes [Hg(NH 3 [Hg 3 (NH) 2 ] 2ϩ [5] and [Hg 2 N] ϩ [5], all based on Millon's seminal work [6]. In these, HgϪN distances are all between 204 and 208 pm with NϪHgϪN angles of 180°. These are apparently the shortest HgϪN distances seen so far in a linear NϪHgϪN arrangement.With a new ligand, the anion of N-imino-methyl-formamide, Imf Ϫ , formed unintentionally when a Hg II -1,2,4-triazole complex was attempted, we have now again observed HgϪN distances at the lower limit, of only 203.5(7) pm in Hg(Imf) 2 . Results and DiscussionMercury(II) bis(N-imino-methyl-formamidate), Hg(Imf) 2 , was obtained from aqueous solutions of 1,2,4-triazole and Hg(NO 3 ) 2 · 2H 2 O. Presumably, HImf has formed through a degradation process of 1,2,4-triazole under the influence of Hg II . Similar degradation processes have been reported for six-membered heterocyclic compounds, pyridazine, pyrimidine and pyrazine, where also HImf has been observed as one of the intermediates [7].The crystal structure contains linear centrosymmetric Hg(Imf) 2 molecules, Fig. 1, with HgϪN distances of only 203.5(7) pm. CϭO and CϭN as well as CϪN distances in the N-imino-methylformamidate "anion" are as one would expect. Four further nitrogen atoms add to a very distorted octahedral effective coordination ( Fig. 1), two of which are intramolecular at d(HgϪN) ϭ

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Synthese und Kristallstruktur von N‐Formylformamidinium‐hexachloroantimonat

Cited by 4 publications

References 16 publications

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

Crystal structures of two formamidinium hexafluoridophosphate salts, one with batch-dependent disorder

Mercuric Bis(N‐imino‐methyl‐formamidate), Hg(Imf)₂

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Synthese und Kristallstruktur von N‐Formylformamidinium‐hexachloroantimonat

Cited by 4 publications

References 16 publications

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl5 at Room Temperature

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl5 at Room Temperature

Crystal structures of two formamidinium hexafluoridophosphate salts, one with batch-dependent disorder

Mercuric Bis(N‐imino‐methyl‐formamidate), Hg(Imf)2

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C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

C−N Bond-Forming Self-Condensation of Amide Promoted by MoCl₅ at Room Temperature

Mercuric Bis(N‐imino‐methyl‐formamidate), Hg(Imf)₂