Dipotassium(I) cyclooctatetraenide–1-methoxy-2-(2-methoxyethoxy)ethane

Noordik, J. H.; Hark, T. E. M. van den; Mooij, J. J.; Klaassen, A. A. K.

doi:10.1107/s0567740874003840

Cited by 43 publications

(23 citation statements)

References 2 publications

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“…(20). The nitrone group in 3 has a longer C=N bond than in 2, and shorter N-0 and C-C(ary1) distances (in the latter case this difference, although not statistically significant, is in the expected direction).…”

Section: Analysis Of Thermal Motionmentioning

confidence: 90%

Structural studies of organoboron compounds. XXI. Crystal and molecular structures of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo-[2.2.2]octane and N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide

Kliegel¹,

Preu²,

Rettig³

et al. 1985

Can. J. Chem.

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. Can. J. Chem. 63, 509 (1985). Crystals of 3-(pheny1methylidene)-4-methyl-I-phenyl-2,6,7-trioxa-3-azonia-I -boratabicyclo[2.2.2]octane are orthorhombic, a = 8.0732(7), b = 11.8499(10), c = 31.679(2) A, Z = 8, space group Pbca, and those of N-(4-nitrophenylmethylidene)-5-methyl-2-p~enyl-l,3-dioxa-2-bora-5-cyclohexaneamine N-oxide are monoclinic, a = 6.1873(6), b = 23.206(2), c = 11.3081(11) A, P = 92.326(5)", Z = 4, space group P2,ln. Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.041 and 0.036 for 943 and 1679 reflections with I 2 3u(l), respectively. Both compounds are condensation products of bis(hydroxyalkyl)nitrones and phenylboronic acid. 3-(Phenylmethylidene)-4-methyl-l-phenyl-2,6,7-trioxa-3-azonia-I-boratabicyclo[2.~.2]octane was found to possess a bicyclic structure resulting from intramolecular 0-B coordination (0-B = 1.604(7) A) and is the first such bicyclic boron compound to be structurally characterized. In N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-I ,3-dioxa-2-bora-5-cyclohexaneamine N-oxide, which has weakened nitrone basicity, the 0-B interaction does not occur, resulting in a monocyclic system incorporating a trigonal planar boron atom. IntroductionThe condensation products of bis(hydroxyalkyl)nitrones such as 1 and phenylboronic acid can generally have an intramolecularly coordinated bicyclo[2.2.2]octane structure 2 and/or a simple monocyclic diester structure 3 (1). Sufficient

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Section: Analysis Of Thermal Motionmentioning

confidence: 90%

Structural studies of organoboron compounds. XXI. Crystal and molecular structures of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo-[2.2.2]octane and N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide

Kliegel¹,

Preu²,

Rettig³

et al. 1985

Can. J. Chem.

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“…43 The crystal structure of COT 2− /2K + has the planar COT dianion sandwiched between the metal cations where the K + ions are centered above and below the ring by approximately 2.3 Å. 44 Such a tight ion pairing arrangement likely exists for each of the three planar COT 2− rings in 2 −6 (e.g., 2 −6 /6K + , see Figure 4 and structure 2 −6 ). A Coulombic attraction between these K + ions and the neighboring oxygen atoms would be expected in this tight ion pairing arrangement, which would enhance the polarity of these carbonyl bonds, structure 2 −6 (dashed lines represent Coulombic attractions).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Tris-[8]annulenyl Isocyanurate Trianion Triradical and Hexa-anion from the Alkali Metal Reduction of [8]Annulenyl Isocyanate

Peters

Klen

2015

J. Org. Chem.

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The solution phase alkali metal reduction of [8]annulenyl isocyanate (C8H7NCO) yields an EPR spectrum, which reveals electron couplings to seven protons and only one nitrogen. Although this strongly suggested that the C8H7NCO anion radical was generated, experiments on the oxidized product reveal the actual reduced species to be tris-[8]annulenyl isocyanurate. Unlike the previously studied phenyl isocyanurate anion radical, the unpaired electron(s) is now localized within an [8]annulenyl moiety. Further exposure to metal results in the formation of an equilibrium mixture of trianion triradical and trianion radical species. The cyclotrimerization to form the isocyanurate is proposed to be driven by a reactive C8H7NCO dianion, which is produced from the large equilibrium disproportionation of the anion radical. Exhaustive reduction of the tris-[8]annulenyl isocyanurate with potassium in THF generates the first-ever observed hexa-anion of an isocyanurate. NMR analysis reveals that the polarity of the carbonyl bonds within this hexa-anion is augmented and is caused by the close proximity of K(+) ions, which are tightly ion paired to the three [8]annulenyl dianion rings. These preliminary studies on the reduction of C8H7NCO suggest that polymeric materials (e.g., polyisocyanates) made from this isocyanate might exhibit unique properties.

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“…For a detailed description on handling the highly air sensitive crystals we also refer to earlier publications (7,9).…”

Section: Magnetic Measurementsmentioning

confidence: 99%

Structure of Alkali Biphenyl Ion Pairs in Solution and in the Solid State

Boer¹,

Klaassen²,

Mooij³

et al. 1979

Ions and Ion Pairs and Their Role in Chemical Reactions

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-NMR experiments on sodium biphenyl (NaBp), potassium biphenyl (KBp) and ribidium biphenyl (RbBp), dissolved in various solvents are summarized with emphasis on the structural information which can be obtained from such experiments. The crystal structures of NaBp.2Tg (Tg = triglyme), KBp.2Ttg and RbBp.2Ttg (Ttg tetraglyme) are discussed, in relation to the NMR results obtained for these systems in solution. In the solid state these crystals may be considered to be built up of solvent separated ion pairs. Magnetic experiments are reported for single crystals of the three systems. Susceptibility measurements revealed a ferromagnetic coupling in NaBp.2Tg and KBp.2Ttg and an antiferromagnetic coupling in RbBp.2Ttg. All crystals exhibit an exchange narrowed ESR line, with an orientation dependent linewidth. From the resonance positions the molecular g tensor of the biphenyl anion could be derived. The orientation dependent linewidth is due to dipolar interactions between the spins. A quantitative explanation of it could not be given at present.

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Dipotassium(I) cyclooctatetraenide–1-methoxy-2-(2-methoxyethoxy)ethane

Cited by 43 publications

References 2 publications

Structural studies of organoboron compounds. XXI. Crystal and molecular structures of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo-[2.2.2]octane and N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide

Structural studies of organoboron compounds. XXI. Crystal and molecular structures of 3-(phenylmethylidene)-4-methyl-1-phenyl-2,6,7-trioxa-3-azonia-1-boratabicyclo-[2.2.2]octane and N-(4-nitrophenylmethylidene)-5-methyl-2-phenyl-1,3-dioxa-2-bora-5-cyclohexaneamine N-oxide

Tris-[8]annulenyl Isocyanurate Trianion Triradical and Hexa-anion from the Alkali Metal Reduction of [8]Annulenyl Isocyanate

Structure of Alkali Biphenyl Ion Pairs in Solution and in the Solid State

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