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Salts And Ionic Liquids Of Resonance Stabilized Amides.

H. Brand, J. Martens, P. Mayer, A. Schulz, Markus Seibald, T. Soller
Published 2009 · Chemistry, Medicine

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The synthesis, structure, and bonding of alkali salts of resonance stabilized amides, such as diformylamide (dfa), formylcyanoamide (fca), nitrocyanoamide (nca), and for comparision, the well-known dicyanoamide (dca), are discussed on the basis of experimental and theoretical data. The first structural reports of K(18-crown-6)+dfa-, K(18-crown-6)+fca-, Na+nca-, and Li(TMEDA)+dca- are presented. Examination of the X-ray data reveals almost planar anions with strong cation-anion interactions resulting in network-like structures in the solid state. For comparison, the X-ray structures of covalently bound phenyldicyanoamide and diformamide are also discussed. The thermal behavior of the alkali salts of these amides is studied by thermoanalytical experiments. Moreover, several novel ionic liquids based on resonance stabilized amides have been prepared and were fully characterized, namely the dfa, fca, and nca salts of EMIM (1-ethyl-3-methyl-imidazolium), BMIM (1-butyl-3-methyl-imidazolium), and HMIM (1-hexyl-3-methyl-imidazolium). Most of them are liquid at room temperature, except BMIM+fca- that melts at 32 degrees C. These ionic liquids are neither heat nor shock sensitive, are thermally stable up to over 200 degrees C, and can be prepared easily in large quantities.
This paper references
10.1021/CM048864X
New Energetic Salts Based on Nitrogen-Containing Heterocycles
H. Xue (2005)
10.1021/ed040p295
The valence-shell electron-pair repulsion (VSEPR) theory of directed valency
R. J. Gillespie (1963)
10.1021/JO060847Z
ZnO as a new catalyst for N-formylation of amines under solvent-free conditions.
M. Hosseini-Sarvari (2006)
10.1021/JA033540F
Ionic Liquids in Synthesis Edited by Peter Wasserscheid (Institute for Technical and Macromolecular Chemistry, Aachen) and Thomas Welton (Imperial College of Science, London). Wiley-VCH: Weinheim. 2003. xvi + 364 pp. $175.00. ISBN 3-527-30515-7.
R. Bartsch (2003)
10.1002/QUA.21235
Vibrational dynamics of hydrogen‐bonded HCN complexes with OH and NH acids: Computational DFT systematic study
J. M. Alía (2007)
10.1021/ja01508a004
Bond Angles and the Spatial Correlation of Electrons1
R. J. Gillespie (1960)
10.1007/978-1-4684-7424-4_24
The Natural Bond Orbital Lewis Structure Concept for Molecules, Radicals, and Radical Ions
F. Weinhold (1988)
10.1002/ANIE.200300620
Noncoordinating anions--fact or fiction? A survey of likely candidates.
I. Krossing (2004)
10.1016/S0022-4596(03)00388-8
Investigation of structural and dynamic properties of NH4[N(CN)2] by means of X-ray and neutron powder diffraction as well as vibrational and solid-state NMR spectroscopy
B. Lotsch (2003)
10.1021/IC048890X
Energetic salts from N-aminoazoles.
H. Xue (2004)
10.1002/ZFCH.19800200729
Chemie der Pseudohalogenide. Von einem Autorenkollektiv unter Leitung von A. M. Golub H. Köhler; VEB Deutscher Verlag der Wissenschaften, Berlin 1979; 440 Seiten mit 38 Bildern und 77 Tabellen; Format 16 × 23 cm, Ln. 88,— M
L. Kolditz (2010)
10.1002/ZAAC.200300286
Phase Transition of a Dicyanamide with Rutile‐like Structure: Syntheses and Crystal Structures of α‐ and β‐Cd[N(CN)2]2
B. Jürgens (2004)
10.1126/SCIENCE.1090287
Solvent-Free Electrolytes with Aqueous Solution-Like Conductivities
W. Xu (2003)
SKW Trostberg AG)
S. Weiss (1979)
10.1016/S1293-2558(02)01325-0
Synthesis, crystal structure, vibrational spectroscopy, and thermal behaviour of lead dicyanamide Pb[N(CN)2]2
B. Jürgens (2002)
10.1021/CM050350Q
Thermal Conversion of Guanylurea Dicyanamide into Graphitic Carbon Nitride via Prototype CNx Precursors
B. Lotsch (2005)
10.1515/9783111419787-003
H
Yu-Qin Cao (1824)
10.1002/1521-3765(20011217)7:24<5372::AID-CHEM5372>3.0.CO;2-#
Trimerization of alkali dicyanamides M[N(CN)2] and formation of tricyanomelaminates M3[C6N9] (M = K, Rb) in the melt: crystal structure determination of three polymorphs of K[N(CN)2], two of Rb[N(CN)2], and one of K3[C6N9] and Rb3[C6N9] from X-ray powder diffractometry.
E. Irran (2001)
10.1021/JA055956U
In situ crystallization of low-melting ionic liquids.
A. Choudhury (2005)
10.1107/S0021889898007717
SIR97: a new tool for crystal structure determination and refinement
A. Altomare (1999)
10.1002/mrc.1260310711
Nitramino, NRNO2 (R = H, CH3), as a substituent. 13C and 15N NMR spectroscopic study of nitraminobenzenes and -pyridines
E. Kolehmainen (1993)
10.1021/IC991044F
Trimerization of NaC2N3 to Na3C6N9 in the solid: ab initio crystal structure determination of two polymorphs of NaC2N3 and of Na3C6N9 from X-ray powder diffractometry.
B. Jürgens (2000)
10.1055/S-2006-932470
Sodium Bis(trimethylsilyl)amide in the ‘One-Flask’ Transformation of ­Isocyanates to Cyanamides
Fung Fuh Wong (2006)
10.1021/JA042232U
Charge separation and efficient light energy conversion in sensitized mesoscopic solar cells based on binary ionic liquids.
P. Wang (2005)
10.1002/cber.19741070213
Röntgenstrukturanalyse des Tetraformylhydrazins
A. Hinderer (1974)
10.1080/00397919208021552
New Method of Pure Diazomethane Preparation
Mohamed Ghazi (1992)
10.1002/ZFCH.19840241008
Diphenoxyphosphoryl‐dicyanamid und Diphenoxyphosphoryl‐cyanocarbodiimid als erste Beispiele bindungsisomerer Dicyanamidderivate: Herrn Professor Dr. Kurt Issleib zum 65. Geburtstag gewidmet
Helmut Koehler (2010)
10.1002/zaac.19875510819
Metall‐Pseudohalogenide. XLI [10]. Über bindungsisomere Organozinn‐dicyanamide
H. Koehler (1987)
10.1021/ja00853a027
Stereochemistry in trivalent nitrogen compounds. XXVIII. Conformational analysis and torsional barriers of imides and triamides
E. Noe (1975)
Synth. Commun. http://www.informaworld.com/smpp/ title%7Econtent = t713597304%7Edb =all%7Etab = issueslist%7Ebranches =332003
K. Kacprzak (2003)
10.1002/mrc.1260280410
15N and 13C NMR study of acylated hydrazines. The instability of trifluoroacethydrazide in the solid state
H. Fritz (1990)
10.1002/cber.19671001110
Über das Diformamid und einige seiner Derivate
E. Allenstein (1967)
10.1246/NIKKASHI.2000.859
Synthesis and Reactions of 6 Amino-4-aryl-2H-1,3,5-thladlazlne-2-thiones.
Koji Takizawa (2000)
10.1016/J.ELECTACTA.2005.02.043
Ion transport properties of lithium ionic liquids and their ion gels
Hitoshi Shobukawa (2005)
New Trends in Research of Energetic Materials
Z. Zeman (2004)
10.1002/chin.197414102
ROENTGENSTRUKTURANALYSE DES TETRAFORMYLHYDRAZINS
Alfred Hinderer (1974)
10.1002/EJOC.200800583
Cyano-, Nitro- and Nitrosomethane Derivatives: Structures and Gas-Phase Acidities
H. Brand (2008)
10.1016/J.THEOCHEM.2005.06.027
Ab initio studies of the conformations of ethynyl formate, cyano formate and related ethynyl and cyano compounds
C. Langley (2005)
10.1021/JP0275894
Ionic liquids: Ion mobilities, glass temperatures, and fragilities
W. Xu (2003)
10.1055/B-004-129729
Spektroskopische Methoden in der organischen Chemie
S. Bienz (2005)
10.1021/IC025800K
Transformation of ammonium dicyanamide into dicyandiamide in the solid.
B. Jürgens (2002)
10.1021/CM049916L
A Binary Ionic Liquid Electrolyte to Achieve ≥7% Power Conversion Efficiencies in Dye-Sensitized Solar Cells
P. Wang (2004)
10.1016/0022-2860(95)09205-6
Solvent effects on the nitrogen NMR shieldings of cyanamide and N,N-dimethyl cyanamide
M. Witanowski (1996)
10.1021/ic50103a022
Crystal structures of dimethyltin(IV) bisdicyanamide and trimethyltin(IV) dicyanamide
Y. M. Chow (1971)
10.1017/CBO9780511614569
Valency and Bonding: Author index
F. Weinhold (2005)
10.1021/JA0255958
Generalized principle of designing neutral superstrong Brønsted acids.
I. Koppel (2002)
SHELXS-97
G. M. Sheldrick (1997)
10.1016/S0277-5387(97)00097-1
Lithium dicyanamide, its reactions with cyanuric chloride, and the crystal structures of LiN(CN)2(MeCN)2 and LiCN(C5H5N)2
A. Purdy (1997)
10.1080/00268976400100021
14N chemical shifts in organic compounds
D. Herbison-Evans (1964)
10.1021/cr00019a005
The search for larger and more weakly coordinating anions
S. Strauss (1993)
10.1021/JP034548E
Ionic Liquids of Chelated Orthoborates as Model Ionic Glassformers
Wu Xu (2003)
10.1021/ja01204a027
Preparation and Properties of N-Methyl-N-nitroso-N'-nitroguanidine
A. McKay (1947)
10.1002/cber.19691021216
Über das N.N-Diformyl-acetamid und das Triformamid
E. Allenstein (1969)
10.1016/0277-5387(95)00365-7
The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes
P. Suárez (1996)
10.1021/AR970230R
Carboranes: A New Class of Weakly Coordinating Anions for Strong Electrophiles, Oxidants, and Superacids
C. Reed (1998)
10.1021/ja01185a516
A new method of preparation of diazomethane.
McKAY Af (1948)
10.1002/ZFCH.19880280825
Zur Kenntnis bindungsisomerer Phenyldicyanamide
Helmut Koehler (2010)
10.1021/JP071823E
Reorientational Dynamics and Solid-Phase Transformation of Ammonium Dicyanamide into Dicyandiamide: A 2H Solid-State NMR Study
B. Lotsch (2007)
10.1002/ZFCH.19890290413
Pseudochalkogenverbindungen; Zur Kenntnis bindungsisomerer Bis(diorganophosphoryl)-cyanamide, [(RO)2-P(O)]2-NCN†
Helmut Koehler (2010)
10.1016/S0022-328X(00)92644-5
Beiträge zur chemie des dicyanamid- und des tricyanmethanid-ions XII. Organosilicum-dicyanamide und -tricyanmethanide☆
Heinz-R. Köhler (1968)
SHELXL-97
G. M. Sheldrick (1997)
10.1016/J.TET.2004.08.028
Effects of geminal disubstitution on C-H and N-H bond dissociation energies
Ke-Sheng Song (2004)
10.1021/jo00019a034
Proton-transfer chemistry of urazoles and related imides, amides, and diacyl hydrazides
M. J. Bausch (1991)
10.1002/ange.19670792003
Elektronenpaar-Abstoßung und Molekülgestalt
R. J. Gillespie (1967)
10.1039/B006901I
Substituent effects on the stability of carbodiimides
D. Tahmassebi (2001)
10.1021/ja01636a042
The Preparation and Reactions of 2-Alkyl-1-(or 3)-nitro-2-thiopseudourea. Part I. Reaction with Amines1
L. Fishbein (1954)
10.1039/B514681J
Highly reversible lithium metal secondary battery using a room temperature ionic liquid/lithium salt mixture and a surface-coated cathode active material.
Shiro Seki (2006)
10.1002/ZAAC.200500479
Synthesis, Crystal Structure and Thermal Behavior of Gadolinium Dicyanamide Dihydrate Gd[N(CN)2]3 · 2 H2O
A. Nag (2006)
10.1002/(SICI)1099-0690(199901)1999:1<287::AID-EJOC287>3.0.CO;2-N
Deprotonation of Amides and Polyfunctional Imides Probed by Heteronuclear NMR and Quantum Chemical Calculations
A. Bagno (1999)
10.5860/choice.43-4035
Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective
F. Weinhold (2005)
10.1002/zaac.19895770118
Synthese und Strukturen bindungsisomerer Alkoxy(aroxy)-phosphoryl-dicyanamide
H. Koehler (1989)
10.1021/ja00790a005
Microwave spectrum and conformation of formimide
W. Steinmetz (1973)
10.1002/ZAAC.200500008
Synthesis, Crystal Structure Determination from X-Ray Powder Diffractometry and Vibrational Spectroscopic Properties of Mg[N(CN)2]2 · 4 H2O
E. Irran (2005)
10.1002/MRC.1260320911
15N NMR chemical shifts for cyanamide, phenylcyanamide and a series of phenyl-substituted derivatives
G. W. Buchanan (1994)
10.1039/B403788J
Towards novel C–N materials: crystal structures of two polymorphs of guanidinium dicyanamide and their thermal conversion into melamine
B. Lotsch (2004)
10.1002/ADMA.200500789
Energetic Ionic Liquids from Azido Derivatives of 1,2,4‐Triazole
H. Xue (2005)
10.1002/ANGE.200300620
Nichtkoordinierende Anionen – Traum oder Wirklichkeit? Eine Übersicht zu möglichen Kandidaten
I. Krossing (2004)
10.1021/IC048513K
Guanidinium-based ionic liquids.
Y. Gao (2005)
10.1016/S0022-328X(00)92990-5
Mössbauer-untersuchungen an einigen organozinnderivaten nicht linearer pseudohalogenide
K. Korecz (1974)
10.1007/978-1-4684-7424-4
The structure of small molecules and ions
R. Naaman (1988)
10.1002/1521-3749(200213)628:13<2901::AID-ZAAC2901>3.0.CO;2-K
Synthesis, Characterization, and Crystal Structures of Various Energetic Urotropinium Salts with Azide, Nitrate, Dinitramide and Azotetrazolate Counter Ions
H. G. Ang (2002)
10.1006/JSSC.2000.9036
Syntheses, vibrational spectroscopy, and crystal structure determination from X-ray powder diffraction data of alkaline earth dicyanamides M[N(CN)2]2 with M = Mg, Ca, Sr, and Ba
B. Jürgens (2001)
10.1016/0166-1280(88)80248-3
Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure
J. E. Carpenter (1988)
10.1002/asia.200700372
Synthesis and structure of monomeric, trimeric, and mixed phenylcyanamides.
H. Brand (2008)
10.1016/J.TET.2005.03.138
2-Cyanopyridazin-3(2H)-ones: effective and chemoselective electrophilic cyanating agents
J. Kim (2005)
10.1016/J.ELECTACTA.2004.01.096
Preparation and transport properties of novel lithium ionic liquids
Hitoshi Shobukawa (2004)
10.1016/S0022-328X(00)90924-0
Beiträge zur chemie des dicyanamid- und des tricyanmethanid-ions XI. Diorganozinn-pseud ohalogenide
Heinz-R. Köhler (1968)
10.1021/IC051751A
Influence of ionic liquids bearing functional groups in dye-sensitized solar cells.
F. Mazille (2006)
10.1002/1521-3749(200012)626:12<2505::AID-ZAAC2505>3.0.CO;2-#
Synthese und Charakterisierung von Natriumcyanamid
M. Becker (2000)
10.1002/zaac.19683590504
Über Triphenylgermanium‐, ‐zinn‐ und ‐bleidicyanamid
H. Koehler (1968)
10.1002/cber.19610941128
IR‐Spektroskopische Untersuchungen am Dicyan‐amid‐Anion, [N(CN)2]⊖
M. Kuhn (1961)
10.1016/J.JSSC.2004.10.030
Synthesis and characterization of the rare-earth dicyanamides Ln [N(CN) 2 ] 3 with Ln =La, Ce, Pr, Nd, Sm, and Eu
B. Jürgens (2005)
10.1021/IC034984F
Characterization of the Thermally Induced Topochemical Solid-State Transformation of NH4[N(CN)2] into NCNC(NH2)2 by Means of X-ray and Neutron Diffraction as Well as Raman and Solid-State NMR Spectroscopy
B. V. Lotsch (2004)
10.1515/9783111576855-015
J
Seguin Hen (1824)
Kyungwon Enterprise Co., Ltd.)
a H.J. Kim (2007)
10.1002/zaac.19865421109
Synthese bindungsisomerer Alkoxy(aroxy)phosphoryl-tricyanmethanide, ein Beitrag zur Pseudohalogenid-Ambivalenz
Helmut Koehler (1986)
10.1017/CBO9780511614569
Valency and Bonding: Contents
F. Weinhold (2005)
10.1002/zaac.19774280113
Metall-Pseudohalogenide. 27. Zur Struktur der Dicyanamide zweiwertiger 3d-Metalle M(N(CN)2)2
Heinz-R. Köhler (1977)
10.1002/POC.1072
Mobility of spin probes in ionic liquids
V. Strehmel (2006)
10.1021/OL017290O
Photoreduction of benzophenones by amines in room-temperature ionic liquids.
J. L. Reynolds (2002)
10.1002/(SICI)1521-3749(199801)624:1<91::AID-ZAAC91>3.0.CO;2-I
Trimerisierung von Dicyanamid-Ionen C2N3– im Festkörper – Synthesen, Kristallstrukturen und Eigenschaften von NaCs2(C2N3)3 und Na3C6N9 · 3 H2O
B. Jürgens (1998)
10.1021/CM0607029
Synthesis and Characterization of Tb[N(CN)2]3·2H2O and Eu[N(CN)2]3·2H2O: Two New Luminescent Rare-Earth Dicyanamides
A. Nag (2006)



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