Home Physical Sciences Polysulfonylamine, CXXVII [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon als Bestandteil dreidimensionaler Wasserstoffbrückenmuster / Polysulfonylamines, CXXVII [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight-Membered Ring Synthon as a Component in Three-Dimensional Hydrogen Bonding Patterns
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Polysulfonylamine, CXXVII [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon als Bestandteil dreidimensionaler Wasserstoffbrückenmuster / Polysulfonylamines, CXXVII [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight-Membered Ring Synthon as a Component in Three-Dimensional Hydrogen Bonding Patterns

  • Karna Wijaya , Oliver Moers , Dagmar Henschel , Armand Blaschette and Peter G. Jones EMAIL logo
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 55 Issue 8

Abstract

In order to study crystal packings and hydrogen bonding frameworks, low-temperature X-ray structures were determined for three onium salts of general formula B H+(MeSO2)2N−, where BH+ is acetamidinium (1, monoclinic, space group P21/c, Z = 4), guanidinium (2, monoclinic, P21/c, Z = 4), or 4,6-diamino-2-thioxo-2,3-dihydropyrimidinium (3, monoclinic P21/n, Z = 4). In every case the ions create three-dimensional N − H ∙∙∙ N/O networks, in which all N − H donors of the cations and four (in 1) or five (2, 3) acceptors of the anion are involved; non-conventional secondary bonds, e.g. C − H ∙∙∙ O/N, do not play an important role in the packings. For the isotypic structures 1 and 2, congruencies and dissimilarities of the hydrogen bonding patterns are discussed in detail. Despite the structural and chemical differences between the cations and the way in which they are attached to the anion, each of the three structures displays a robust eight-membered ring synthon [N2 = R22(8), antidromic] constructed via two-centre hydrogen bonds from a syn, syn-sequence H − N − C (sp2) −N −H of the respective cation and a V-shaped O − S (sp3) − N fragment of the anion. Although the networks in 2 and 3 contain several N − H (∙∙∙ O)2 three-centre interactions, the two-point connectivity of the synthon is distinctly preserved. The results indicate that the (MeSO2)2N− ion may be utilized in crystal engineering as a dependable building block.

Keywords: Di(methanesulfonyl)amide; Onium Cation; Synthon Robustness
Received: 2000-3-23
Published Online: 2014-6-2
Published in Print: 2000-8-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. The Effect of Different Hydrogen Bonding Schemes on Melting Points of Two Isomeric 2-Hydroxy-bornane-3-carboxylic Acids
  2. Hydrogen Bonds in "Carboxyoximes": the Case of Bomane Derivatives
  3. Thermal Decomposition of Prussian Blue Analogues of the Type Fe[Fe(CN)5NO]
  4. Kristallstruktur, Schwingungsspektren und Normalkoordinatenanalyse von trans-(Et4N)[OsF4Cl2] / Crystal Structure, Vibrational Spectra and Normal Coordinate Analysis of trans-(Et4N)[OsF4Cl2]
  5. Synthesis and Crystal Structure of New Ternary Chalcogenides of Group IV Metals: K2ZrS4, Rb2ZrS4, and Rb2HfS4
  6. The Crystal Structures and Thermal Behaviour of the Mercury Arsenates Hg2(H2AsO4)2, Hg2As2O6 and HgAs2O6
  7. Hydrido(acylenolato)cobalt(III)-Verbindungen mit Trimethylphosphan- Liganden: Insertionsreaktionen mit Alkinen und die ersten Carbonylcobalt(III)-Komplexe / Hydrido(acylenolato)cobalt(III) Compounds Containing Trimethylphosphane Ligands: Insertion Reactions with Alkynes and the First Carbonylcobalt(III) Complexes
  8. Spektroskopische Charakterisierung und Kristallstruktur von Trifluormethyliod(III)-bis(trifluoracetat) CF3I(OCOCF3)2 / Spectroscopic Characterisation and Crystal Structure of Trifluoromethyliodine(III) Bis-trifluoroacetate, CF3I(OCOCF3)2
  9. Übergangsmetallkomplexe mit Schwefelliganden, 145 [1]. [Ru(NO)('pybuS4')]Br, ein Komplex mit [Ru(NO)(NS4)]-Gerüst, aktivierten CH2-Gruppen und interionischen Wechselwirkungen im Festkörper ['pybuS4'2- = 2,6-Bis(2-mercapto-3,5-di-terM>utylphenylthio) dimethylpyridin(2-)] / Transition Metal Complexes with Sulfur Ligands, 145 [1]. [Ru(NO)('pybuS4 ')]Br, a Complex with [Ru(NO)(NS4)] Core, Activated CH2 Groups, and Interionic Interactions in the Solid State ('pybuS4'2- = 2,6-Bis(2-mercapto-3,5-di-terf-butylphenylthio)dimethylpyridine(2-))
  10. Darstellung und Strukturanalyse von Lithium- [tetrakis-(methylamino-)aluminat] / Preparation and Crystal Structure of Lithium[tetrakis-(methylamino-)aluminate]
  11. tBuN=V[P(SiMe3)2]3 : Das erste Beispiel eines stabilen Phosphanidovanadium(V)-Komplexes / tBuN=V[P(SiMe3)2]3: The First Example of a Stable Phosphanidovanadium(V) Complex
  12. Polysulfonylamine, CXXVI [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon in Koexistenz mit einem dritten Wasserstoffbrückenmotiv - Cyclodimere, Ketten, supramolekulare Bindungsisomere und ein fünffach verwobenes dreidimensionales (C-H ∙∙∙ O - Netzwerk / Polysulfonylamines, CXXVI [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight- Membered Ring Synthon in Coexistence with a Third Hydrogen Bonding Motif - Cyclodimers, Chains, Supramolecular Linkage Isomers, and a Quintuply Interwoven Three-Dimensional C - H ∙∙∙ O Network
  13. Polysulfonylamine, CXXVII [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon als Bestandteil dreidimensionaler Wasserstoffbrückenmuster / Polysulfonylamines, CXXVII [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight-Membered Ring Synthon as a Component in Three-Dimensional Hydrogen Bonding Patterns
  14. Kristallstruktur und spektroskopische Charakterisierung von Hexamethyl- disilazan-Aluminiumtrichlorid [(H3C)3Si]2NH ∙ AlCl3 / Crystal Structure and Spectroscopic Characterisation of Hexamethyl- disilazane-trichloroalum inum [(H3C)3Si]2NH ∙ AlCl3
  15. 19β → 28-Lactonization of Pomonic Acid from Lantana camara roots
  16. ERRATUM
https://doi.org/10.1515/znb-2000-0813
Keywords for this article
Di(methanesulfonyl)amide; Onium Cation; Synthon Robustness

Articles in the same Issue

  1. The Effect of Different Hydrogen Bonding Schemes on Melting Points of Two Isomeric 2-Hydroxy-bornane-3-carboxylic Acids
  2. Hydrogen Bonds in "Carboxyoximes": the Case of Bomane Derivatives
  3. Thermal Decomposition of Prussian Blue Analogues of the Type Fe[Fe(CN)5NO]
  4. Kristallstruktur, Schwingungsspektren und Normalkoordinatenanalyse von trans-(Et4N)[OsF4Cl2] / Crystal Structure, Vibrational Spectra and Normal Coordinate Analysis of trans-(Et4N)[OsF4Cl2]
  5. Synthesis and Crystal Structure of New Ternary Chalcogenides of Group IV Metals: K2ZrS4, Rb2ZrS4, and Rb2HfS4
  6. The Crystal Structures and Thermal Behaviour of the Mercury Arsenates Hg2(H2AsO4)2, Hg2As2O6 and HgAs2O6
  7. Hydrido(acylenolato)cobalt(III)-Verbindungen mit Trimethylphosphan- Liganden: Insertionsreaktionen mit Alkinen und die ersten Carbonylcobalt(III)-Komplexe / Hydrido(acylenolato)cobalt(III) Compounds Containing Trimethylphosphane Ligands: Insertion Reactions with Alkynes and the First Carbonylcobalt(III) Complexes
  8. Spektroskopische Charakterisierung und Kristallstruktur von Trifluormethyliod(III)-bis(trifluoracetat) CF3I(OCOCF3)2 / Spectroscopic Characterisation and Crystal Structure of Trifluoromethyliodine(III) Bis-trifluoroacetate, CF3I(OCOCF3)2
  9. Übergangsmetallkomplexe mit Schwefelliganden, 145 [1]. [Ru(NO)('pybuS4')]Br, ein Komplex mit [Ru(NO)(NS4)]-Gerüst, aktivierten CH2-Gruppen und interionischen Wechselwirkungen im Festkörper ['pybuS4'2- = 2,6-Bis(2-mercapto-3,5-di-terM>utylphenylthio) dimethylpyridin(2-)] / Transition Metal Complexes with Sulfur Ligands, 145 [1]. [Ru(NO)('pybuS4 ')]Br, a Complex with [Ru(NO)(NS4)] Core, Activated CH2 Groups, and Interionic Interactions in the Solid State ('pybuS4'2- = 2,6-Bis(2-mercapto-3,5-di-terf-butylphenylthio)dimethylpyridine(2-))
  10. Darstellung und Strukturanalyse von Lithium- [tetrakis-(methylamino-)aluminat] / Preparation and Crystal Structure of Lithium[tetrakis-(methylamino-)aluminate]
  11. tBuN=V[P(SiMe3)2]3 : Das erste Beispiel eines stabilen Phosphanidovanadium(V)-Komplexes / tBuN=V[P(SiMe3)2]3: The First Example of a Stable Phosphanidovanadium(V) Complex
  12. Polysulfonylamine, CXXVI [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon in Koexistenz mit einem dritten Wasserstoffbrückenmotiv - Cyclodimere, Ketten, supramolekulare Bindungsisomere und ein fünffach verwobenes dreidimensionales (C-H ∙∙∙ O - Netzwerk / Polysulfonylamines, CXXVI [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight- Membered Ring Synthon in Coexistence with a Third Hydrogen Bonding Motif - Cyclodimers, Chains, Supramolecular Linkage Isomers, and a Quintuply Interwoven Three-Dimensional C - H ∙∙∙ O Network
  13. Polysulfonylamine, CXXVII [1] Wasserstoffbrücken in kristallinen Onium-dimesylamiden: Ein robustes Achtring-Synthon als Bestandteil dreidimensionaler Wasserstoffbrückenmuster / Polysulfonylamines, CXXVII [1] Hydrogen Bonding in Crystalline Onium Dimesylamides: A Robust Eight-Membered Ring Synthon as a Component in Three-Dimensional Hydrogen Bonding Patterns
  14. Kristallstruktur und spektroskopische Charakterisierung von Hexamethyl- disilazan-Aluminiumtrichlorid [(H3C)3Si]2NH ∙ AlCl3 / Crystal Structure and Spectroscopic Characterisation of Hexamethyl- disilazane-trichloroalum inum [(H3C)3Si]2NH ∙ AlCl3
  15. 19β → 28-Lactonization of Pomonic Acid from Lantana camara roots
  16. ERRATUM
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