Ring asymmetry in 4-morpholinobenzenediazonium tetrafluoroborate: crystallographic and SCF studies

Alcock, Nathaniel W.; Greenhough, Trevor J.; Hirst, David M.; Kemp, Terence J.; Payne, David R.

doi:10.1039/p29800000008

Cited by 7 publications

(5 citation statements)

References 1 publication

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“…The diazonium group N9− N8−C3 is in plane with the triazole ring showing an angle of almost 180°(∠N9−N8−C3:179.9(2)°). The diazonium N8− N9 bond length of 1.096(3) Å is virtually identical to those found in various diazonium cations 14,16,17 and inner diazonium salts 12,18 clearly indicating a NN triple bond (1.10 Å 19 ). The C3−N8 bond length (1.365(3) Å) is in the range of common C sp 2 −N bond lengths (1.34−1.37 Å).…”

supporting

confidence: 69%

Isolation of a Moderately Stable but Sensitive Zwitterionic Diazonium Tetrazolyl-1,2,3-triazolate

2016

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An unexpected formation of a diazonium compound was observed by nitration of an amino substituted triazolyl tetrazole with mixed acid. The crystal structure determination revealed a zwitterionic diazonium tetrazolyl-1,2,3-triazolate, whose constitution was supported by NMR and vibrational spectroscopic analysis. The thermal stability and sensitivity toward impact and friction were determined. In contrast, diazotriazoles are rather unstable and are mainly handled in solution and/or low temperatures, which is not the case for this diazonium tetrazolyl-1,2,3-triazolate, being stable at ambient temperature.

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supporting

confidence: 69%

Isolation of a Moderately Stable but Sensitive Zwitterionic Diazonium Tetrazolyl-1,2,3-triazolate

2016

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“…While the difference between these two distances is only just significant, it is interesting that the C(arene)-N(amino) distance is consistently shorter than the C(arene)-N(diazo) distance, which is what would be expected if both forms "E" and " F contribute to the observed structure. These observations are supported by similar results observed in the structure of the morpholino derivative (5). Observing the effect of a "quinoidal" form on the C-C distances in the benzene ring is somewhat more difficult due to the small differences involved compared to their associated standard deviations.…”

Section: Methodssupporting

confidence: 76%

“…However, success was not obtained until the p-diethyl derivative was crystallized as the hexafluorophosphate salt. The results of the structural analysis of this compound are presented herein and these, as expected, correlate closely with those of the similar compound pmorpholinobenzenediazonium tetrafluoroborate (5).…”

supporting

confidence: 56%

The crystal structure of p-diethylaminobenzenediazonium hexafluorophosphate

Ball¹,

Elofson²

1985

Can. J. Chem.

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p-Diethylaminobenzenediazonium hexafluorophosphate, C10H14N3+•PF6−, crystallized in space group [Formula: see text] with a = 12.105(4), b = 12.340(5), c = 10.439(4) Å, α = 96.53(3), β = 104.11(3), γ = 64.44(3)°, and Z = 4. The structure was solved using direct methods and refined with full-matrix least-squares techniques on F, to a final R of 0.054 for 1917 reflections with F2 > 3σ(F2). The mean bond lengths for the diazo group are: N—N 1.096(6); C—N 1.357(7) Å. The geometry of the molecule is discussed in terms of the possible resonance forms and it is shown to be consistent with a form in which the N—N triple bond is essentially intact and the aminobenzene moiety has "quinoidal" character.

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“…25 Interionic association in the layers is complemented by extensive hydrogen-bonding between ortho-hydrogens and neighboring anions (vide supra), but these can be deformed or even broken when they are overwhelmed by stronger steric/electronic interactions. The latter can be influenced either by (a) bulky ortho-substituents as in o-dimethylaminobenzenediazonium tetrafluoroborate, 26 or (b) uncharged (but strongly coordinating) σ-donor groups such as morpholinyl, 27 acetic acid, 17 or a crown-ether, 16 or both, as in o-carboxybenzenediazo-nium chloride monohydrate. 28 Furthermore, planar (nonspherical) anions, such as nitrate, can complicate the layered structure, 13 although it still persists with such odd-shaped anions as bis(trifluoromethanesulfonyl)methanide 29 or o-benzenedisulfonimide.…”

Section: Molecular Network With Arenediazonium Tectonsmentioning

confidence: 99%

Arenediazonium Salts as Versatile (meso-Ionic) Tectons. Charge-Transfer Intercalates and Clathrates in Unusual Crystalline Networks Self-Assembled with Neutral Aromatic π-Donors

Lindeman

Kochi

2004

Crystal Growth & Design

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The surprisingly uniform crystal packings of various arenediazonium salts (ArN 2 + X -) largely consist of two-dimensional ionic layers from various (N 2 + ‚‚‚X -) interactions coupled with a series of antiparallel arrays of pendant aryl groups (Ar). This crystalline architecture can be deliberately modified by the introduction of different (neutral) aromatic π-donors. On the basis of the exceptional electron-acceptor strength of the (N 2 + ) group, the principal crystal-forming interactions of the arenediazonium tecton can be dissected into (a) strong coordination to anionic and electron-rich (neutral) σ-donors within the equatorial plane, (b) enhanced capacity for (C-H‚‚‚X) hydrogen bonding, and (c) remarkable aptitude to form (noncovalent) charge-transfer bonds with aromatic π-donors. Thus, the detailed analysis of crystalline networks found in 3,5-dinitro and 4-carboethoxy derivatives of benzenediazonium salts recognizes them as remarkable intercalate and clathrate structures in which various charge-transfer interactions between the electron-deficient arene moiety and aromatic π-donors are essential for the stabilization of the unusual layered/network structures.

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Ring asymmetry in 4-morpholinobenzenediazonium tetrafluoroborate: crystallographic and SCF studies

Cited by 7 publications

References 1 publication

Isolation of a Moderately Stable but Sensitive Zwitterionic Diazonium Tetrazolyl-1,2,3-triazolate

Isolation of a Moderately Stable but Sensitive Zwitterionic Diazonium Tetrazolyl-1,2,3-triazolate

The crystal structure of p-diethylaminobenzenediazonium hexafluorophosphate

Arenediazonium Salts as Versatile (meso-Ionic) Tectons. Charge-Transfer Intercalates and Clathrates in Unusual Crystalline Networks Self-Assembled with Neutral Aromatic π-Donors

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