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Formation and Structure of Cinchona Alkaloid (Bis-2,3-naphthalenediyl)orthoborate Salts

  • Maciej Kubicki EMAIL logo , Teresa Borowiak , Krystyna Gawrońska and Jacek Gawroński
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 55 Issue 11

A series of (bis-2,3-naphthalenediyl)orthoborate salts of Cinchona alkaloids has been synthesized and characterized. The interactions between ions in the salts have been studied by means of circular dichroism spectroscopy and X-ray crystal structure determination. The CD spectra of the dihydroquinidine salt show that in non-polar solvents it exists as a tightly held ion pair. The crystal structure of the cinchonidine salt proves the existence of ions in the solid state. The protonation takes place at the quinuclidine nitrogen atom. The hydrogen bonds connect cation and anion into one recognizable unit. Additional hydrogen bonds (with hydroxy group as a hydrogen donor and quinoline nitrogen atom as an acceptor) form infinite chains of cations along the [001] direction. There are cavities in the crystal structure that are partially filled by solvent molecules (acetone).

Keywords : Cinchona Alkaloids; Association Modes; Hydrogen Bonds
Received: 2000-8-4
Published Online: 2014-6-2
Published in Print: 2000-11-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Generation of Bis[2,6-di(4-methoxy-phenyl)phenyl]plumbylene and its Insertion into n-Butyliodide to Give a Tetrahedral Triorganolead(IV) Iodide
  2. Tris[(triphenylphosphine)gold(I)]oxonium Dihydrogentrifluoride as the Product of an Attempted Preparation of [(Triphenylphosphine)gold(I)] Fluoride
  3. Crystal and Molecular Structures of the Functional Lithium Cyclopentadienides [Li(tmeda)][R2PCMe2C5H4], R = Ph, Me
  4. CD-Spectroscopic Investigations for the Determination of the Absolute Configuration of α-Alkylated 1,4-CycIohexanedione Derivatives
  5. Carbacylamidophosphates: Synthethis and Structure of N,N'-Tetramethyl-N''-p-chlorobenzoyIphosphoryltriamide and N,N'-Tetramethyl-NM-o-fluorobenzoylphosphoryltriamide
  6. The Hydrogen Bond Networks in Nicinquinium Salts
  7. Condensed [PtIn3/3] and [PtIn6/6] Units as Structural Motifs in ScPtln, TbPtln, and HoPtln
  8. Darstellung, 11B-, 13C-NMR- und Schwingungsspektren von Cs2[B6H5(p-C6H4(NO2))] und Cs2[B6H5(C6H3-l-(CH3)-5-(NO2))] sowie Kristallstruktur von (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN / Preparation, 11B , 13C-NMR and Vibrational Spectra of Cs2[B6H5(p-C6H4(NO2))], Cs2[B6H5 (C6H3-1 -(CH3 )-5-(NO2))] and Crystal Structure of (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN
  9. Uniform Sidearm Derivatisations in a Tetrapodal Pentaamine: Ligands with NN4 O4 Donor Sets, and a Bis(Ferrocenecarbaldehyde Aminal)
  10. Die Kristallstrukturen von Phenylen-1,4-bis(4-nitrophenylsulfonamid) und seines Dinatrium(tetramethanol-dihydrat)-Salzes / Interaction in Molecular Crystals, 161 [1, 2]. The Crystal Structures of Phenylene-1,4- bis(4-nitrophenylsulfonamide) and of its Disodium(tetramethanol-dihydrate) Salt
  11. Wechselwirkungen in Molekülkristallen, 162 [1, 2]. Di(arylsulfonyl)amine – geeignete Liganden für lipophil umhüllte Polyionen-Aggregate mit Cs⊕ -Schichten variabler Dicke / Interaction in Molecular Crystals, 162 [1, 2]. Di(arylsulfonyl)amines – Ligands for Lipophilically Wrapped Polyion Aggregates with Cs⊕ -Layers of Variable Thickness
  12. Crystal Structure and Magnetic Properties of a Binuclear Copper(II) Complex Bridged by an Alkoxo-oxygen Atom and an Acetate Ion
  13. Transition Metal Complexes of Derivatized Chiral Dihydro-1,2,4-triazin-6-ones. Part III [1]. X-Ray Crystal Structure Analysis of N,N’-Bis[(1-phenyl-5-isopropyl-4,5-dihydro-6-oxo-1,2,4-triazin-3-yl)ethylidene]- propane-1,3-diamine Nickel(II)
  14. X-Ray Crystal Structure Analysis of Substituted 5-(2,3-Dihydro-7-benzofuryl)- 2-methylpyrazolo[4,3-d]pyrimidin-7-one (iso-Biagra) [1]
  15. Formation and Structure of Cinchona Alkaloid (Bis-2,3-naphthalenediyl)orthoborate Salts
  16. Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones
  17. 3-Hexyne Complexes of M olybdenum(II) and Tungsten(II) Containing 2, 2 '-Bipyridine. X-Ray Crystal Structure of [MoI2(CO)(bipy)(η2-EtC2Et)]
  18. 3.4-D ihydro-1, 2, 3, 4-tetramethyl- pentafulvalene and its Conversion to Ferrocenes
https://doi.org/10.1515/znb-2000-1115
Keywords for this article
Cinchona Alkaloids; Association Modes; Hydrogen Bonds

Articles in the same Issue

  1. Generation of Bis[2,6-di(4-methoxy-phenyl)phenyl]plumbylene and its Insertion into n-Butyliodide to Give a Tetrahedral Triorganolead(IV) Iodide
  2. Tris[(triphenylphosphine)gold(I)]oxonium Dihydrogentrifluoride as the Product of an Attempted Preparation of [(Triphenylphosphine)gold(I)] Fluoride
  3. Crystal and Molecular Structures of the Functional Lithium Cyclopentadienides [Li(tmeda)][R2PCMe2C5H4], R = Ph, Me
  4. CD-Spectroscopic Investigations for the Determination of the Absolute Configuration of α-Alkylated 1,4-CycIohexanedione Derivatives
  5. Carbacylamidophosphates: Synthethis and Structure of N,N'-Tetramethyl-N''-p-chlorobenzoyIphosphoryltriamide and N,N'-Tetramethyl-NM-o-fluorobenzoylphosphoryltriamide
  6. The Hydrogen Bond Networks in Nicinquinium Salts
  7. Condensed [PtIn3/3] and [PtIn6/6] Units as Structural Motifs in ScPtln, TbPtln, and HoPtln
  8. Darstellung, 11B-, 13C-NMR- und Schwingungsspektren von Cs2[B6H5(p-C6H4(NO2))] und Cs2[B6H5(C6H3-l-(CH3)-5-(NO2))] sowie Kristallstruktur von (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN / Preparation, 11B , 13C-NMR and Vibrational Spectra of Cs2[B6H5(p-C6H4(NO2))], Cs2[B6H5 (C6H3-1 -(CH3 )-5-(NO2))] and Crystal Structure of (CH2Py2)[B6Cl5(p-C6H4(NO2))]·CH3CN
  9. Uniform Sidearm Derivatisations in a Tetrapodal Pentaamine: Ligands with NN4 O4 Donor Sets, and a Bis(Ferrocenecarbaldehyde Aminal)
  10. Die Kristallstrukturen von Phenylen-1,4-bis(4-nitrophenylsulfonamid) und seines Dinatrium(tetramethanol-dihydrat)-Salzes / Interaction in Molecular Crystals, 161 [1, 2]. The Crystal Structures of Phenylene-1,4- bis(4-nitrophenylsulfonamide) and of its Disodium(tetramethanol-dihydrate) Salt
  11. Wechselwirkungen in Molekülkristallen, 162 [1, 2]. Di(arylsulfonyl)amine – geeignete Liganden für lipophil umhüllte Polyionen-Aggregate mit Cs⊕ -Schichten variabler Dicke / Interaction in Molecular Crystals, 162 [1, 2]. Di(arylsulfonyl)amines – Ligands for Lipophilically Wrapped Polyion Aggregates with Cs⊕ -Layers of Variable Thickness
  12. Crystal Structure and Magnetic Properties of a Binuclear Copper(II) Complex Bridged by an Alkoxo-oxygen Atom and an Acetate Ion
  13. Transition Metal Complexes of Derivatized Chiral Dihydro-1,2,4-triazin-6-ones. Part III [1]. X-Ray Crystal Structure Analysis of N,N’-Bis[(1-phenyl-5-isopropyl-4,5-dihydro-6-oxo-1,2,4-triazin-3-yl)ethylidene]- propane-1,3-diamine Nickel(II)
  14. X-Ray Crystal Structure Analysis of Substituted 5-(2,3-Dihydro-7-benzofuryl)- 2-methylpyrazolo[4,3-d]pyrimidin-7-one (iso-Biagra) [1]
  15. Formation and Structure of Cinchona Alkaloid (Bis-2,3-naphthalenediyl)orthoborate Salts
  16. Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones
  17. 3-Hexyne Complexes of M olybdenum(II) and Tungsten(II) Containing 2, 2 '-Bipyridine. X-Ray Crystal Structure of [MoI2(CO)(bipy)(η2-EtC2Et)]
  18. 3.4-D ihydro-1, 2, 3, 4-tetramethyl- pentafulvalene and its Conversion to Ferrocenes
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