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Polysulfonylamine, CXLIII [1], Rolle schwacher Wasserstoffbrücken (C - H···O) in den Kristallstrukturen von 2,6-Dimethylpyridinium-, 1-Hydroxypyridinium- und Imidazolium-dimesylamid / Polysulfonylamines, CXLIII [1], Role of Weak Hydrogen Bonds (C - H···O) in the Crystal Structures of 2,6-Dimethylpyridinium , 1-Hydroxypyridinium and Imidazolium Dimesylamide

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Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 56 Issue 10

In order to study hydrogen bonding networks in ionic crystals, low-temperature X-ray structures were determined for three onium salts of general formula BH+(MeSO2)2N- , where BH+ is 2,6-dimethylpyridinium (1; monoclinic, space group P21/c, Z′ = 1), 1-hydroxypyridinium (2; triclinic, P1̅, Z′ = 1), or imidazolium (3; monoclinic, Cc, Z′ = 1). The asymmetric units consist of cation-anion pairs assembled in 1 and 3 by ordinary N+ - H···N hydrogen bonds, in 2 by a very short N+ - O - H···N- bond belonging to the class (+/-)CAHB [H···O 148(3), O···N 253.5(2) pm, O - H···N 175(3)°]. The second N -H donor of the imidazolium ion is involved in a nearly symmetric N - H (···O)2 three-centre bond to two different anions. In the pyridine derivatives, the (MeSO2 )2N- ions are associated via short C(sp3) - H···O contacts to form a three-dimensional framework of corrugated and cross-linked layers (1) or an assembly of discrete corrugated layers (2). As a common feature, these anion substructures are pervaded by hexagonal channels parallel to x, each one accommodating two stacks of cations that are linked to the channel walls by the unique strong hydrogen bond and a set of short Car - H···O contacts; moreover, cations drawn from adjacent stacks in structure 2 create inversion-symmetric dimers based upon a short Car - H···O(H) - N interaction. In contrast, the structure of 3 displays planar anion layers assembled by short C(sp3 ) - H···O contacts, intercalating the cations with their ring planes perpendicular to the layer planes and binding them by means of the strong hydrogen bonds and three Car -H···O interactions. All C - H···O taken into consideration have normalized parameters d( H···O) ≤ 267 pm and θ(C - H···O) ≥ 121°.

Keywords : Di(methanesulfonyl)amide; Weak Hydrogen Bonding; Very Short Heteronuclear Hydrogen Bond
Received: 2001-7-4
Published Online: 2014-6-2
Published in Print: 2001-10-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Darstellung und Strukturaufklärung von Tricäsiumundecaphosphid- Ammoniakat(1/3) Cs3P11 · 3 NH3 / Synthesis and Crystal Structure of Tricesium Undecaphosphide-Ammonia(l/3) Cs3P11 · 3 NH3
  2. Magnetic Properties and Crystal Structure of a 3,5-Dimethylpyrazolate-Bridged Binuclear Copper(II) Complex
  3. Enantioselective Catalysis, 139 [1]. A Chiral Cyclic Amidine Containing a Pyridine Substituent - Synthesis, Coordination Chemistry, Catalysis
  4. Tetraberyllium-η4-oxo-hexa(arylcarboxylates)
  5. Drei Formen des Samarium(III)-Sulfidselenids Sm2S2-xSe1+x (0,1 ≤ x < 0,2) / Tree Types of the Samarium(III) Sulfide Selenide Sm2S2-xSe1+x (0,1 ≤ x < 0,2)
  6. Investigations on the Thermal Decomposition of Coordination Polymers Based on Copper(I) Halides and 2-Methylpyrazine
  7. Crystal Structure and Tautomerism of 1-[N-(4-Iodophenyl)]aminomethylidene-2(1H)naphthalenone
  8. N-Silylaminotin Trichlorides. Synthesis and Characterisation by Multinuclear Magnetic Resonance Spectroscopy
  9. Synthese und Eigenschaften von 2-Cyanimino-l,3-dimethylimidazolin [1] / Synthesis and Properties of 2-Cyanimino-l,3-dimethylimidazoline [1]
  10. Synthesis and Crystal Structure of (dmaaH)2(dmaH)2[P12Sn12N12(NH)2] · 4 dmaa, dmaa = N,N-Dimethylacetamide, dma = Dimethylamine, an Anhydrous Example of the P12N14Cage
  11. Synthesen, Kristallstrukturen und magnetische Eigenschaften von [Li(12-Krone-4)2][Li(12-Krone-4)(OH2)]2[Nb6Cl18], [Li(15-Krone-5)2(OH2)]3[Nb6Cl18] und [(18-Krone-6)2(O2H5)]3[Nb6Cl18] / Syntheses, Crystal Structures and Magnetic Behaviour of [Li(12-Krone-4)2][Li(12-Krone-4)(OH2)]2[Nb6Cl18], [Li(15-Krone-5)2(OH2)]3[Nb6Cl18] and [(18-Krone-6)2(O2H5)]3[Nb6Cl18]
  12. Investigation of the Thionation Reaction of Cyclic Imides
  13. Polysulfonylamine, CXLII [1]. Ein supramolekulares Monomer-Dimer-Paar: Starke und schwache Wasserstoffbrücken in den Kristallstrukturen von Pyridinium-dimesylamid und 4,4´-Bipyridindiium-bis(dimesylamid) / Polysulfonylamines, CXLII [1]. A Supramolecular Monomer-Dimer Pair: Strong and Weak Hydrogen Bonding in the Crystal Structures of Pyridinium Dimesylamide and 4,4´-Bipyridinediium Bis(dimesylamide)
  14. Polysulfonylamine, CXLIII [1], Rolle schwacher Wasserstoffbrücken (C - H···O) in den Kristallstrukturen von 2,6-Dimethylpyridinium-, 1-Hydroxypyridinium- und Imidazolium-dimesylamid / Polysulfonylamines, CXLIII [1], Role of Weak Hydrogen Bonds (C - H···O) in the Crystal Structures of 2,6-Dimethylpyridinium , 1-Hydroxypyridinium and Imidazolium Dimesylamide
  15. Synthesis and Structural Studies of 5, 11, 17, 23-Tetrahydroxyresorc[4]arenes
  16. Enaminones as Building Blocks In Heterocyclic Synthesis: A New One Pot Synthesis of Polyfunctional Substituted Pyridines
  17. Remangilone D, a New Bisnoroleanane Triterpene, and a New Flavone from Physena madagascariensis [1]
  18. Notizen: Metallkomplexe mit biologisch wichtigen Liganden, CXXXIX [1], Ein Ferrocenylen-verbrücktes Pseudohexapeptid Fe[C5H4CH 2OGlyValOMe(Val-Boc)]2 / Metal Complexes of Biologically Important Ligands, CXXXIX [1]. A Ferrocenylene Bridged Pseudohexapeptide Fe[C5H4CH 2OGlyValOMe(Val-Boc)]2
https://doi.org/10.1515/znb-2001-1014
Keywords for this article
Di(methanesulfonyl)amide; Weak Hydrogen Bonding; Very Short Heteronuclear Hydrogen Bond

Articles in the same Issue

  1. Darstellung und Strukturaufklärung von Tricäsiumundecaphosphid- Ammoniakat(1/3) Cs3P11 · 3 NH3 / Synthesis and Crystal Structure of Tricesium Undecaphosphide-Ammonia(l/3) Cs3P11 · 3 NH3
  2. Magnetic Properties and Crystal Structure of a 3,5-Dimethylpyrazolate-Bridged Binuclear Copper(II) Complex
  3. Enantioselective Catalysis, 139 [1]. A Chiral Cyclic Amidine Containing a Pyridine Substituent - Synthesis, Coordination Chemistry, Catalysis
  4. Tetraberyllium-η4-oxo-hexa(arylcarboxylates)
  5. Drei Formen des Samarium(III)-Sulfidselenids Sm2S2-xSe1+x (0,1 ≤ x < 0,2) / Tree Types of the Samarium(III) Sulfide Selenide Sm2S2-xSe1+x (0,1 ≤ x < 0,2)
  6. Investigations on the Thermal Decomposition of Coordination Polymers Based on Copper(I) Halides and 2-Methylpyrazine
  7. Crystal Structure and Tautomerism of 1-[N-(4-Iodophenyl)]aminomethylidene-2(1H)naphthalenone
  8. N-Silylaminotin Trichlorides. Synthesis and Characterisation by Multinuclear Magnetic Resonance Spectroscopy
  9. Synthese und Eigenschaften von 2-Cyanimino-l,3-dimethylimidazolin [1] / Synthesis and Properties of 2-Cyanimino-l,3-dimethylimidazoline [1]
  10. Synthesis and Crystal Structure of (dmaaH)2(dmaH)2[P12Sn12N12(NH)2] · 4 dmaa, dmaa = N,N-Dimethylacetamide, dma = Dimethylamine, an Anhydrous Example of the P12N14Cage
  11. Synthesen, Kristallstrukturen und magnetische Eigenschaften von [Li(12-Krone-4)2][Li(12-Krone-4)(OH2)]2[Nb6Cl18], [Li(15-Krone-5)2(OH2)]3[Nb6Cl18] und [(18-Krone-6)2(O2H5)]3[Nb6Cl18] / Syntheses, Crystal Structures and Magnetic Behaviour of [Li(12-Krone-4)2][Li(12-Krone-4)(OH2)]2[Nb6Cl18], [Li(15-Krone-5)2(OH2)]3[Nb6Cl18] and [(18-Krone-6)2(O2H5)]3[Nb6Cl18]
  12. Investigation of the Thionation Reaction of Cyclic Imides
  13. Polysulfonylamine, CXLII [1]. Ein supramolekulares Monomer-Dimer-Paar: Starke und schwache Wasserstoffbrücken in den Kristallstrukturen von Pyridinium-dimesylamid und 4,4´-Bipyridindiium-bis(dimesylamid) / Polysulfonylamines, CXLII [1]. A Supramolecular Monomer-Dimer Pair: Strong and Weak Hydrogen Bonding in the Crystal Structures of Pyridinium Dimesylamide and 4,4´-Bipyridinediium Bis(dimesylamide)
  14. Polysulfonylamine, CXLIII [1], Rolle schwacher Wasserstoffbrücken (C - H···O) in den Kristallstrukturen von 2,6-Dimethylpyridinium-, 1-Hydroxypyridinium- und Imidazolium-dimesylamid / Polysulfonylamines, CXLIII [1], Role of Weak Hydrogen Bonds (C - H···O) in the Crystal Structures of 2,6-Dimethylpyridinium , 1-Hydroxypyridinium and Imidazolium Dimesylamide
  15. Synthesis and Structural Studies of 5, 11, 17, 23-Tetrahydroxyresorc[4]arenes
  16. Enaminones as Building Blocks In Heterocyclic Synthesis: A New One Pot Synthesis of Polyfunctional Substituted Pyridines
  17. Remangilone D, a New Bisnoroleanane Triterpene, and a New Flavone from Physena madagascariensis [1]
  18. Notizen: Metallkomplexe mit biologisch wichtigen Liganden, CXXXIX [1], Ein Ferrocenylen-verbrücktes Pseudohexapeptid Fe[C5H4CH 2OGlyValOMe(Val-Boc)]2 / Metal Complexes of Biologically Important Ligands, CXXXIX [1]. A Ferrocenylene Bridged Pseudohexapeptide Fe[C5H4CH 2OGlyValOMe(Val-Boc)]2
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