Isolation and Structure of a Hydrogen-bonded 2,2′:6′,2′′-Terpyridin-4′-one Acetic Acid Adduct

2014 ◽  
Vol 67 (4) ◽  
pp. 651 ◽  
Author(s):  
Pas Florio ◽  
Campbell J. Coghlan ◽  
Chih-Pei Lin ◽  
Kei Saito ◽  
Eva M. Campi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Solid State ◽  
Ammonium Acetate ◽  
Condensation Reaction ◽  
Acetate Salt ◽  
Pyridine Nitrogen ◽  
Acid Adduct ◽  
Hydrogen Bonded

Herein, we report the crystal structure of a key intermediate in the synthesis of 4′-substituted-terpyridines. Our findings confirm that the terpyridin-4′-one intermediate as generated from the condensation reaction of the corresponding triketone precursor with ammonium acetate is isolated as a hydrogen-bonded adduct with acetic acid, and not, as previously reported, as the acetate salt of a protonated pyridine nitrogen. This finding provides a rationale for the behaviour and structure of substituted terpyridin-4′-ones and pyridones in both the solid state and in solution.

Hydrogen bonded dimers of ketocoumarin in the solid state and alcohol:water binary solvent: fluorescence spectroscopy, crystal structure and DFT investigation

2019 ◽  
Vol 43 (23) ◽  
pp. 9090-9105 ◽  
Author(s):  
Kannan Ramamurthy ◽  
E. J. Padma Malar ◽  
Chellappan Selvaraju
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Binary Mixture ◽  
Fluorescence Spectroscopy ◽  
Emission Spectrum ◽  
Fluorescence Emission ◽  
Binary Solvent ◽  
Fluorescence Emission Spectrum ◽  
Hydrogen Bonded

Fluorescence emission spectrum of ketocoumarin dimers in an alcohol:water binary mixture and the solid state.

Crystal structures of 7-azaindole, an unusual hydrogen-bonded tetramer, and of two of its methylmercury(II) complexes

1990 ◽  
Vol 68 (1) ◽  
pp. 193-201 ◽  
Author(s):  
Pascal Dufour ◽  
Yves Dartiguenave ◽  
Michèle Dartiguenave ◽  
Nathalie Dufour ◽  
Anne-Marie Lebuis ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nitrogen Atom ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Membered Ring ◽  
Pyridine Nitrogen Atom ◽  
Nitrate Ions ◽  
Pyridine Nitrogen ◽  
Independent Molecules ◽  
Hydrogen Bonded

Crystals of 7-azaindole ([Formula: see text], a = 11.312(4), b = 14.960(6), c = 15.509(5) Å, α = 102.86(3), β = 108.78(3), γ = 90.71(3)°, Z = 16, R = 0.052) contain tetrameric units of approximate S4 symmetry, in which the molecules are associated by means of four complementary N—H … N hydrogen bonds. [CH3Hg(7-azaindole)]NO3 ([Formula: see text], a = 7.818(3), b = 7.884(3), c = 9.135(4) Å, α = 97.89(3), β = 109.13(3), γ = 103.28(3)°, Z = 2, R = 0.039) contains well-separated nitrate ions and complex cations in which the methylmercury group is linearly bonded to the pyridine nitrogen atom, whereas the five-membered ring remains protonated. In the neutral [CH3Hg(azaindolate)] complex ([Formula: see text], a = 10.926(10), b = 11.333(8), c = 11.647(10) Å, α = 92.13(8), β = 104.83(9), γ = 111.86(7)°, Z = 6, R = 0.048), methylmercury groups have substituted the N—H proton in the five-membered ring for the three symmetry-independent molecules. Intermolecular secondary Hg … N bonds are found with pyridine nitrogens. Keywords: azaindole, methylmercury, crystal structure.

Preparation and Crystal Structure of the Potentially Tridentate Substituted Phenoxyacetic Acid (2-Benzoyl-5-methoxyphenoxy)acetic Acid and Its Complex Adduct With Sodium

1995 ◽  
Vol 48 (4) ◽  
pp. 869 ◽  
Author(s):  
G Smith ◽  
EJ Oreilly ◽  
SA See ◽  
KA Byriel ◽  
CHL Kennard
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Carboxy Group ◽  
Intramolecular Hydrogen Bonding ◽  
Ligand Molecule ◽  
Phenoxyacetic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

The ring-substituted phenoxyacetic acid (2-benzoyl-5-methoxyphenoxy)acetic acid (HL) (3) and its complex adduct dimer (4) with sodium, [Na2(L)2(HL)2].2HL, have been synthesized and their structures determined by X-ray diffraction. The acid (3) does not have the usual cyclic hydrogen-bonded dimer association, but instead has three-centre intramolecular hydrogen bonding between the carboxyl proton and both the ether and keto oxygens [O---O, 2.602(3), 2.711(3) Ǻ respectively]. Each sodium in the centrosymmetric complex dimer (4) is seven-coordinate [Na-O, 2.313(5)-2.612(5) Ǻ], involving the 'inner' three oxygens of both a protonated and an ionic ligand molecule. In addition, one of these carboxyl oxygens forms a bridge to the inversion-related sodium, while the uncoordinated carboxyl oxygen is hydrogen-bonded to a protonated carboxy group [O---O, 2.464(8) Ǻ]. The molecules of the lattice acid have only one hydrogen-bonded association with the second uncoordinated carboxy group in the dimer [O---O, 2.513(7) Ǻ].

The Hexakis(N,N'-Dimethylurea)Cobalt(Ii) Cation: A Flexible Building Block for the Construction of Hydrogen Bonded Networks

2003 ◽  
Vol 58 (1) ◽  
pp. 74-84 ◽  
Author(s):  
Giannis S. Papaefstathiou ◽  
Robby Keuleers ◽  
Constantinos J. Milios ◽  
Catherine P. Raptopoulou ◽  
Aris Terzis ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Spectroscopic Data ◽  
Low Frequency ◽  
Great Stability ◽  
Structure Determinations ◽  
Interionic Hydrogen ◽  
Hydrogen Bonded

AbstractThe ligand N.N'-dimethylurea (DMU) is used to propagate the octahedral coordination geom- etry of [Co(DMU)6]2+ into 1D and 2D assemblies via a combination of coordinative bonds and interionic hydrogen-bonding. Compounds [Co(DMU)6](ClO4)2 (1), [Co(DMU)6](BF4)2 (2) and [Co(DMU)6](NO3)2 (3) have been prepared from the reactions of DMU and the appropriate hydrated cobalt(II) salts in EtOH. MeCN or Me2CO (only for 1) in the presence of 2,2-di- methoxypropane. Crystal structure determinations demonstrate the existence of [Co(DMU)6]2+ cations and CIO4- , BF4- or NO3- counterions. The great stability of the [Co(DMU)6]2+ cation in the solid state is attributed to a pseudochelate effect which arises from the existence of strong intracationic N-H···O(DMU) hydrogen bonds. The [Co(DMU)6]2+ cations and counterions self- assemble to form a hydrogen-bonded ID architecture in 1, and different 2D hydrogen-bonded networks in 2 and 3. The precise nature of the resulting supramolecular structure is influenced by the nature of the counterion. Two main motifs of intermolecular (interionic) hydrogen bonds have been observed: N-H ···O(ClO4-, NO3-) or N-H ··· F(BF4-) and weak C-H F(BF4- ) or C-H-O(NO3- ) hydrogen bonds. The complexes were also characterized by vibrational spec- troscopy (IR, far-IR. low-frequency Raman). The spectroscopic data are discussed in terms of the nature of bonding and the know;n structures.

scholarly journals Hydrogen-Bonded Networks Based on Cobalt(II), Nickel(II), and Zinc(II) Complexes of N,N'-Diethylurea

2010 ◽  
Vol 2010 ◽  
pp. 1-12 ◽  
Author(s):  
Labrini Drakopoulou ◽  
Catherine P. Raptopoulou ◽  
Aris Terzis ◽  
Giannis S. Papaefstathiou
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Vibrational Spectroscopy ◽  
Supramolecular Structures ◽  
Counter Ion ◽  
Structure Determinations ◽  
Hydrogen Bonded

N,N'-diethylurea (DEU) was employed as a ligand to form the octahedral complexes[M(DEU)6]2+(M=Co, Ni and Zn). Compounds[Co(DEU)6](BF4)2(1),[Co(DEU)6](CIO4)2(2),[Ni(DEU)6](CIO4)2(3), and[Zn(DMU)6](CIO4)2(4) have been prepared from the reactions of DEU and the appropriate hydrated metal(II) salts in EtOH in the presence of 2,2-dimethoxypropane. Crystal structure determinations demonstrate the existence of[M(DEU)6]2+cations andCIO4-(in2–4) orBF4-(in1) counterions. The[M(DEU)6]2+cations in the solid state are stabilized by apseudochelateeffect due to the existence of six strong intracationicN-H⋯O(DEU)hydrogen bonds. The[M(DEU)6]2+cations and counterions self-assemble to form hydrogen-bonded 2D architectures in2–4that conform to thekgd(kagome dual) network, and a 3D hydrogen-bondedrtl(rutile) network in1. The nature of the resulting supramolecular structures is influenced by the nature of the counter-ion. The complexes were also characterized by vibrational spectroscopy (IR).

N,N,N′-Triacetyl-2,6-diamino-4-tert-butylanisole

2006 ◽  
Vol 62 (4) ◽  
pp. o1300-o1301
Author(s):  
Matthew I. J. Polson ◽  
Peter J. Steel
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Benzene Ring ◽  
Title Compound ◽  
State Structure ◽  
Solid State Structure ◽  
Compound C ◽  
Hydrogen Bonded

The solid state structure of the title compound, C17H24N2O4, reveals the imide unit to be planar and perpendicular to the plane of the benzene ring. In the crystal structure, adjacent molecules are hydrogen bonded through the amide unit.

Copper(II) acetates: from dimer to monomer

1985 ◽  
Vol 63 (1) ◽  
pp. 52-56 ◽  
Author(s):  
Patrick Sharrock ◽  
Milan Melník
Keyword(s):  
Acetic Acid ◽  
Solid State ◽  
Acid Solution ◽  
Acetic Acid Solution ◽  
Epr Spectra ◽  
Frozen Solution ◽  
Dissociation Mechanism ◽  
Hyperfine Splittings ◽  
Acid Adduct

The epr spectra at various frequencies of copper(II) acetate anhydrous, monohydrate, monoacetic acid, and water – acetic acid adduct are presented and analysed. The presence of copper hyperfine splittings in the solid state epr spectra of this series of compounds is discussed. The frozen solution spectrum of copper(II) acetate in acetic acid solution containing ~2% water shows an exceptional resolution of [Formula: see text] hyperfine of 24 G. This is attributed to a key intermediate which explains the monomer–dimer dissociation mechanism. The influence of distortions on the structures of these compounds is presented.

Metal-(phenylthio)alkanoic acid interactions—XII the crystal structure of potassium (4-chloro-2,5-dimethylphenylthio)-acetate-(4-chloro-2,5-dimethylphenylthio)acetic acid adduct

Polyhedron ◽  
1989 ◽  
Vol 8 (17) ◽  
pp. 2147-2150
Author(s):  
Colin H.L. Kennard ◽  
Graham Smith ◽  
Thomas C.W. Mak ◽  
Wai-Hing Yip ◽  
Wing-hong Chan
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Alkanoic Acid ◽  
Acid Adduct

[Sm(CH3COO)3(H2O)2] · CH3COOH, ein Essigsäureaddukt des Samarium(III)-acetatdihydrates [Sm(CH3COO)3(H2O)2] · CH3COOH, an Acetic Acid Adduct of Samarium(III) Acetate Dihydrate

1992 ◽  
Vol 47 (2) ◽  
pp. 179-182 ◽  
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Single Crystal ◽  
Acetate Dihydrate ◽  
Trigonal System ◽  
Acid Adduct

The crystal structure of the acetic acid adduct of the so far unknown samarium(III) acetate dihydrate was determined from single-crystal four-circle diffractometer data. It has the composition [Sm (CH3COO)3(H2O)2] CH3COOH containing {[Sm(CH3COO)3(H2O)2]}2 dimers and crystallizes in the trigonal system, R3̄̄̄̄, a = 2695.1(3), c = 1030.8(4) pm, Vm = 216.97(5) cm3/mol, R = 0.041, Rw = 0.030.

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