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Crystal Structure and Thermal Solid-State Reactivity of Ammonium Cyanoureate NH4[H2NC(=O)NCN]

  • Bettina V. Lotsch and Wolfgang Schnick
Published/Copyright: February 24, 2022
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 59 Issue 11-12

Abstract

The ammonium salt of cyanourea NH4[H2NC(=O)NCN] has been synthesised via an acid-base route from the parent acid and characterized by single-crystal and powder X-ray diffraction,NMR and vibrational spectroscopy, mass spectrometry as well as thermal analysis. The molecular salt (P21/c, a = 388.95(8), b = 1121.0(2), c = 1096.4(2) pm, β = 92.57(3)◦, V = 477.5(2)・106 pm3, Z = 4, T = 140 K) which may formally be derived from the related compound ammonium dicyanamide NH4[N(CN)2] by addition of one molecule water, consists of isolated ammonium and cyanoureate ions which are assembled via H・ ・ ・N and H・ ・ ・O hydrogen bonds, forming a three-dimensional arrangement. At elevated temperatures, ammonium cyanoureate undergoes a complex transformation affording the formation of urea and cyanoguanylurea H2NC(=O)NHC(NH2)=NCN or the isomeric ammeline (C3N3)(NH2)2(OH) as the main products, depending on the reaction conditions. The transformation is accompanied by consecutive reactions such as proton transfer and the dis- and reassembly of molecular fragments, yielding a macroscopic segregation of the reaction products. The conversion represents yet another example of a complex reaction proceeding in the solid-state.

Key words: Solid-State Reaction; Crystal Structure; Cyanourea; Thermal Reactivity
Published Online: 2022-02-24
Published in Print: 2004-12-01

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Professor Hubert Schmidbaur zum 70. Geburtstag
  2. Synthese und Reaktionsverhalten von {[Hf](μ-σ,π-C≡CR)2 }Ni(CO); die Röntgenstrukturanalyse von [(η5-C5H4SiMe3)2Hf(C≡CtBu)]2O / Synthesis and Reaction Behaviour of {[Hf](μ −σ ,π -C≡CR)2}Ni(CO); the Solid-State Structure of [(η5–C5H4SiMe3)2Hf(C≡CtBu)]2O
  3. Indirect Nuclear Spin-Spin Coupling Constants nJ(11B, 1H) and nJ(11B, 11B) in Some Boron Hydrides - Density Functional Theory (DFT) Calculations
  4. High-Temperature Synthesis, Crystal Structure, and Properties of the New Sodium Rare-Earth Oxide Borates Na2RE2(BO3)2O (RE = Dy, Ho)
  5. Spectroscopic Investigation of the System TeCl4/[NEt4]PF6 in Solution and the Crystal Structure of [NEt4]2[Te2Cl10]
  6. Hydroalumination of Nitriles and Isonitriles
  7. Molybdenum(VI) cis-Dioxo Complexes with Chiral Schiff Base Ligands: Synthesis, Characterization, and Catalytic Applications
  8. Crystal Structure and Thermal Solid-State Reactivity of Ammonium Cyanoureate NH4[H2NC(=O)NCN]
  9. Structural Chemistry of Titanium Alkoxides Substituted by the Chelating Bidentate Ligands Isoeugenolate or 2-Aminoethanolate
  10. Formation and Structure of a Bis(cyclopentadienyl)(formamidinato)zirconium Cation Complex
  11. Nucleophilic Aromatic Substitution of 2-(3(5)-Pyrazolyl)pyridine: A Novel Access to Multidentate Chelate Ligands
  12. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Copper(I) Cyanide with Pyridine Bases
  13. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Silver(I) Cyanide with (Oligo-)Pyridine Bases
  14. Syntheses, Structures and Vibrational Spectroscopy of Some Mixed Pyridine/Triphenylphosphine Adducts of Copper(I) Cyanide
  15. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Copper(I) Cyanide with Unidentate Organic Nitriles
  16. Syntheses, Structures and Vibrational Spectroscopy Studies of Copper(I) Perchlorate : Benzonitrile Adducts (1 : n) of n = 2, 3, 4, 5 Stoichiometry
  17. Solvothermal Synthesis of [C6H17N3]Sb10S16: A New Thioantimonate(III) with an in-situ Formed Organic Amine Cation
  18. Self-Assembly of a Cd2+Compound with 4-Pyridylthioacetic Acid: Structural and Luminescence Properties
  19. Synthesis, Crystal Structure and Thermal Decomposition Reaction of the New Copper(I) Cyanide Coordination Polymer Poly[tri-μ2-cyano-C,N)- bis(μ2-2,3-dimethyl-pyrazine-N,N)]tricopper(I)
  20. Selective Substitution of Hex2SiFCl for the Preparation of Polymers with Two Different Alternate π-Electron Systems Linked by Hex2Si Units
  21. Novel Five- and Six-Membered Diazasilacycloalkanes: Synthesis, Structure and Properties
  22. First X-Ray Structure of a Cationic Silicon Complex with Salen-Type Ligand: An Unusual Compound with Two Different Si-N Dative Bonds
  23. Synthesis and Derivatization of Homoleptic Dinuclear Lanthanide Siloxide Complexes
  24. Silver(I) Complexes with the 1,1’-Bis(diethyldithiocarbamate)ferrocene Ligand. Polymeric Chain Species
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  27. Pt-Dumbbells in Ba3Pt2: Interplay of Geometric and Relativistic Effects on Pt–Pt Bonding
  28. Random Interstitial Halide Accommodation in an α,ω-Alkylidene-diammonium Template
  29. Multidentate Aminoalkoxides. Synthesis and Complexation Behavior to Lithium and Sodium
  30. Crystal and Molecular Structure of P(C6H5)5 · 0.5 THF
  31. N-Benzyl- und N-Heptyl-substituierte Tetraazacyclododecane / N-Benzyl and N-Heptyl Substituted Tetraazacyclodecanes
  32. Metal Complexes of Biologically Important Ligands, CLVI [1]. Metal Complexes of 4-Iodo-L-phenylalanine. Oxidative Addition of 4-Iodo-L-phenylalanine Ester to Palladium(0)
  33. Secondary Interactions in Gold(I) Complexes with Thione Ligands, 3. Three Ionic Dimesylamides [1, 2]
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  36. The Modulated Structure of SrAuSn2
  37. Synthesis and Structure of the Helicate (M)-(–)-[Pt2 {(R,R)-tetraphos}2](CF3SO3)4 · 4.5 H2O
  38. Synthesis and Reactivity of Novel Alkali Metal Stannides
  39. N-Aryl Anions: Half Way between Amides and Carbanions
  40. Oxidative Addition of Methyl Iodide to Dinuclear Gold(I) Amidinate Complex: Schmidbaur’s Breakthrough Reaction Revisited with Amidinates
  41. Polymorphism of Trimeric Perfluoro-ortho-phenylene Mercury, [Hg(o-C6F4)]3
  42. Macrocyclic Gold(I) Complexes with Bridging Diacetylide and Diphosphine Ligands
  43. Trioxorhenium(VII) Complexes with Imidazolin-2-iminato Ligands
  44. Synthesis and Characterization of Cl2HSi-O-NMe2
  45. Strukur und Reaktivität von Al2Cp*+ in der Gasphase. Ein experimenteller Beitrag zur Problematik der Aluminium-Aluminium- Doppelbindung / Structure and Reactivity of Al2Cp*+ in the Gas Phase. Experiments on the Problematic Nature of the Aluminum-Aluminum-Multiple Bond
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  48. Organoaluminium and -gallium Lewis-Acid Adducts of Tetramethylmethylenediamine
  49. Synthesis and Reactivity of Ti(III) Tris(tert-butoxy)siloxy Complexes
  50. (EtZn)4Zn2(PSitBu3)4 – a Homometallic Phosphanediide of Zinc with a Novel Zn6P4 Cage
  51. Ordnung und Fehlordnung der Anionen in tetragonalen Boridcarbiden der Seltenerdmetalle / Order and Disorder of Anions in Tetragonal Boride Carbides of Rare Earth Metals
  52. Binuclear Ten-Membered Ring Cyclometallated Complexes of Digold(I) and their Reactions with Iodine and Bromine
  53. Bis-, Tris- and Tetrakis(lithiomethyl)germanes: New Building Blocks for Organogermanium Compounds
  54. Synthesis and Crystal Structure Analysis of C60 Fulleride Dianions in Solvates of [A([2.2.2]crypt)]2[C60] (A = K, Rb, Cs)
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https://doi.org/10.1515/znb-2004-11-1241
Keywords for this article
Solid-State Reaction; Crystal Structure; Cyanourea; Thermal Reactivity

Articles in the same Issue

  1. Professor Hubert Schmidbaur zum 70. Geburtstag
  2. Synthese und Reaktionsverhalten von {[Hf](μ-σ,π-C≡CR)2 }Ni(CO); die Röntgenstrukturanalyse von [(η5-C5H4SiMe3)2Hf(C≡CtBu)]2O / Synthesis and Reaction Behaviour of {[Hf](μ −σ ,π -C≡CR)2}Ni(CO); the Solid-State Structure of [(η5–C5H4SiMe3)2Hf(C≡CtBu)]2O
  3. Indirect Nuclear Spin-Spin Coupling Constants nJ(11B, 1H) and nJ(11B, 11B) in Some Boron Hydrides - Density Functional Theory (DFT) Calculations
  4. High-Temperature Synthesis, Crystal Structure, and Properties of the New Sodium Rare-Earth Oxide Borates Na2RE2(BO3)2O (RE = Dy, Ho)
  5. Spectroscopic Investigation of the System TeCl4/[NEt4]PF6 in Solution and the Crystal Structure of [NEt4]2[Te2Cl10]
  6. Hydroalumination of Nitriles and Isonitriles
  7. Molybdenum(VI) cis-Dioxo Complexes with Chiral Schiff Base Ligands: Synthesis, Characterization, and Catalytic Applications
  8. Crystal Structure and Thermal Solid-State Reactivity of Ammonium Cyanoureate NH4[H2NC(=O)NCN]
  9. Structural Chemistry of Titanium Alkoxides Substituted by the Chelating Bidentate Ligands Isoeugenolate or 2-Aminoethanolate
  10. Formation and Structure of a Bis(cyclopentadienyl)(formamidinato)zirconium Cation Complex
  11. Nucleophilic Aromatic Substitution of 2-(3(5)-Pyrazolyl)pyridine: A Novel Access to Multidentate Chelate Ligands
  12. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Copper(I) Cyanide with Pyridine Bases
  13. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Silver(I) Cyanide with (Oligo-)Pyridine Bases
  14. Syntheses, Structures and Vibrational Spectroscopy of Some Mixed Pyridine/Triphenylphosphine Adducts of Copper(I) Cyanide
  15. Syntheses, Structures and Vibrational Spectroscopy of Some Adducts of Copper(I) Cyanide with Unidentate Organic Nitriles
  16. Syntheses, Structures and Vibrational Spectroscopy Studies of Copper(I) Perchlorate : Benzonitrile Adducts (1 : n) of n = 2, 3, 4, 5 Stoichiometry
  17. Solvothermal Synthesis of [C6H17N3]Sb10S16: A New Thioantimonate(III) with an in-situ Formed Organic Amine Cation
  18. Self-Assembly of a Cd2+Compound with 4-Pyridylthioacetic Acid: Structural and Luminescence Properties
  19. Synthesis, Crystal Structure and Thermal Decomposition Reaction of the New Copper(I) Cyanide Coordination Polymer Poly[tri-μ2-cyano-C,N)- bis(μ2-2,3-dimethyl-pyrazine-N,N)]tricopper(I)
  20. Selective Substitution of Hex2SiFCl for the Preparation of Polymers with Two Different Alternate π-Electron Systems Linked by Hex2Si Units
  21. Novel Five- and Six-Membered Diazasilacycloalkanes: Synthesis, Structure and Properties
  22. First X-Ray Structure of a Cationic Silicon Complex with Salen-Type Ligand: An Unusual Compound with Two Different Si-N Dative Bonds
  23. Synthesis and Derivatization of Homoleptic Dinuclear Lanthanide Siloxide Complexes
  24. Silver(I) Complexes with the 1,1’-Bis(diethyldithiocarbamate)ferrocene Ligand. Polymeric Chain Species
  25. Pyrrole Thioaldehyde Complexes of Nickel, Palladium and Platinum
  26. Luminescent Gold(I)-Thallium(I) Arrays through N-Bidentate Building Blocks
  27. Pt-Dumbbells in Ba3Pt2: Interplay of Geometric and Relativistic Effects on Pt–Pt Bonding
  28. Random Interstitial Halide Accommodation in an α,ω-Alkylidene-diammonium Template
  29. Multidentate Aminoalkoxides. Synthesis and Complexation Behavior to Lithium and Sodium
  30. Crystal and Molecular Structure of P(C6H5)5 · 0.5 THF
  31. N-Benzyl- und N-Heptyl-substituierte Tetraazacyclododecane / N-Benzyl and N-Heptyl Substituted Tetraazacyclodecanes
  32. Metal Complexes of Biologically Important Ligands, CLVI [1]. Metal Complexes of 4-Iodo-L-phenylalanine. Oxidative Addition of 4-Iodo-L-phenylalanine Ester to Palladium(0)
  33. Secondary Interactions in Gold(I) Complexes with Thione Ligands, 3. Three Ionic Dimesylamides [1, 2]
  34. A Novel Crown-Ether Stabilized Oxonium Halogenochalcogenate(IV): [H7O3(Bis-dibromo-dibenzo-30-crown-10)][Se2Br9]·1.5CH2Cl2
  35. Intramolecular Carbene and Carbenoid Reactions of α-(Vinyloxy)silyl-α-diazoacetates
  36. The Modulated Structure of SrAuSn2
  37. Synthesis and Structure of the Helicate (M)-(–)-[Pt2 {(R,R)-tetraphos}2](CF3SO3)4 · 4.5 H2O
  38. Synthesis and Reactivity of Novel Alkali Metal Stannides
  39. N-Aryl Anions: Half Way between Amides and Carbanions
  40. Oxidative Addition of Methyl Iodide to Dinuclear Gold(I) Amidinate Complex: Schmidbaur’s Breakthrough Reaction Revisited with Amidinates
  41. Polymorphism of Trimeric Perfluoro-ortho-phenylene Mercury, [Hg(o-C6F4)]3
  42. Macrocyclic Gold(I) Complexes with Bridging Diacetylide and Diphosphine Ligands
  43. Trioxorhenium(VII) Complexes with Imidazolin-2-iminato Ligands
  44. Synthesis and Characterization of Cl2HSi-O-NMe2
  45. Strukur und Reaktivität von Al2Cp*+ in der Gasphase. Ein experimenteller Beitrag zur Problematik der Aluminium-Aluminium- Doppelbindung / Structure and Reactivity of Al2Cp*+ in the Gas Phase. Experiments on the Problematic Nature of the Aluminum-Aluminum-Multiple Bond
  46. Pd(II) Complexes of N-Allyl Substituted N-Heterocyclic Carbenes
  47. Formamidinium Salts of Low Valent Metal Halide Anions MX3 – (M = Ge, Sn) and M2X62– (M = Ga, In)
  48. Organoaluminium and -gallium Lewis-Acid Adducts of Tetramethylmethylenediamine
  49. Synthesis and Reactivity of Ti(III) Tris(tert-butoxy)siloxy Complexes
  50. (EtZn)4Zn2(PSitBu3)4 – a Homometallic Phosphanediide of Zinc with a Novel Zn6P4 Cage
  51. Ordnung und Fehlordnung der Anionen in tetragonalen Boridcarbiden der Seltenerdmetalle / Order and Disorder of Anions in Tetragonal Boride Carbides of Rare Earth Metals
  52. Binuclear Ten-Membered Ring Cyclometallated Complexes of Digold(I) and their Reactions with Iodine and Bromine
  53. Bis-, Tris- and Tetrakis(lithiomethyl)germanes: New Building Blocks for Organogermanium Compounds
  54. Synthesis and Crystal Structure Analysis of C60 Fulleride Dianions in Solvates of [A([2.2.2]crypt)]2[C60] (A = K, Rb, Cs)
  55. Gold-Thiolate Clusters: A Relativistic Density Functional Study of the Model Species Au13(SR)n, R = H, CH3, n = 4, 6, 8
  56. The Zinc Aqua Complex of a Tetrapodal Pentaamine Ligand and its Reactivity towards Carbon Dioxide
  57. Mono- and Binuclear Gold(I) Amido Compounds of Purine Derivatives
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