scholarly journals 3-Phenyl-N,N,N′,N′-tetramethyl-1-ethyne-1-carboximidamidium bromide

2012 ◽  
Vol 68 (6) ◽  
pp. o1812-o1812 ◽  
Author(s):  
Ioannis Tiritiris ◽  
Willi Kantlehner
Keyword(s):  
Double Bond ◽  
Title Compound ◽  
Triple Bond ◽  
Positive Charge ◽  
Bond Distance ◽  
Double Bond Character ◽  
Acetylenic Bond ◽  
Compound C ◽  
Bond Character

The reaction of 3,3,3-tris(dimethylamino)-1-phenylprop-1-yne with bromine in pentane yields the title compound, C13H17N2 +·Br−. The acetylenic bond distance [1.197 (2) Å] is consistent with a C[triple-bond]C triple bond. The amidinium C=N bonds [1.325 (2) and 1.330 (2) Å] have double-bond character and the positive charge is delocalized between the two dimethylamino groups.

scholarly journals N-(Pyrazin-2-yl)adamantane-1-carboxamide

IUCrData ◽  
2016 ◽  
Vol 1 (8) ◽  
Author(s):  
Błażej Dziuk ◽  
Borys Ośmiałowski ◽  
Krzysztof Ejsmont ◽  
Bartosz Zarychta
Keyword(s):  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Amide Bond ◽  
Torsion Angles ◽  
Double Bond Character ◽  
Pyrazine Ring ◽  
Compound C ◽  
Bond Character ◽  
Good Agreement

Molecules of the title compound, C15H19N3O, are composed of an adamantine unit and a pyrazine ring connected to each other through an amide bond. The H—N—C=O moiety is close to planar [C—N—C—O and C—N—C—C torsion angles of 4.7 (2) and −173.8 (1)°, respectively]. The N3—C5 bond has partial double-bond character [1.370 (1) Å]. The geometries of the pyrazine ring and the adamantane substituent are normal and in good agreement with closely related structures. In the crystal, molecules are connected by N—H...O hydrogen bonds, forming zigzag chains in the [001] direction and are arranged in a herringbone fashion.

scholarly journals 2-(6-Bromobenzo[d]thiazol-2-yl)-5,5-dimethylthiazol-4(5H)-one

2013 ◽  
Vol 69 (12) ◽  
pp. o1821-o1821
Author(s):  
Hendryk Würfel ◽  
Helmar Görls ◽  
Dieter Weiss ◽  
Rainer Beckert
Keyword(s):  
Molecular Structure ◽  
Double Bond ◽  
Torsion Angle ◽  
Title Compound ◽  
Carbon Bond ◽  
Double Bond Character ◽  
Compound C ◽  
Carbon Carbon Bond ◽  
Bond Character ◽  
Reflux Temperature

The title compound, C12H9BrN2OS2, was obtained by reacting 6-bromobenzo[d]thiazole-2-carbonitrile iniso-propanol with ethyl 2-mercapto-2-methylpropanoate at reflux temperature for several hours. The resulting dimethyloxyluciferin derivative shows partial double-bond character of the carbon–carbon bond between the two heterocyclic moieties [C—C = 1.461 (3) Å]. This double bond restricts rotation around this C—C axis, therefore leading to an almost planar molecular structure [N—C—C—S torsion angle = 9.7 (3)°]. The five-membered thiazoline ring is not completely planar as a result of the bulky S atom [C—S—C—C torsion angle = 5.17 (12)°].

scholarly journals Tris(N,N,N′,N′,N′′,N′′-hexaethylguanidinium) dodecaiodidotribismuthate(III)

IUCrData ◽  
2016 ◽  
Vol 1 (3) ◽  
Author(s):  
Ioannis Tiritiris ◽  
Georg Knobloch ◽  
Stefan Saur ◽  
Willi Kantlehner
Keyword(s):  
Double Bond ◽  
Title Compound ◽  
Asymmetric Unit ◽  
Charge Delocalization ◽  
Double Bond Character ◽  
Iodide Ions ◽  
Bond Lengths ◽  
Compound C ◽  
Bond Character

The asymmetric unit of title compound, (C13H30N3)3[Bi3I12], comprises one cation and two independent (1/6) fragments of the [Bi3I12]3−ions. The C—N bond lengths in the guanidinium ion range from 1.340 (4) to 1.345 (4) Å, indicating partial double-bond character pointing towards charge delocalization within the NCN planes. The BiIIIions are distorted octahedrally coordinated by six iodide ions, with Bi—I bond lengths ranging from 2.9206 (3) to 3.3507 (3) Å. Three [BiI6]3−octahedra are fused together through face-sharing, forming a trinuclear [Bi3I12]3−unit.

scholarly journals 4-Fluoro-N-methyl-N-nitroaniline

IUCrData ◽  
2016 ◽  
Vol 1 (9) ◽  
Author(s):  
Katarzyna Gajda ◽  
Błażej Dziuk ◽  
Zdzisław Daszkiewicz
Keyword(s):  
Double Bond ◽  
Hydrogen Bonds ◽  
Bond Length ◽  
Aromatic Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Double Bond Character ◽  
Compound C ◽  
Bond Character

Molecules of the title compound, C7H7FN2O2, are composed of a nitramine group which is twisted with the respect to the aromatic ring, with an N—N—C—C torsion angle of −117.38 (12)°. In the molecule, the N—N bond length [1.3510 (15) Å] indicates some double-bond character, while the angle between the aromatic ring and the nitramine group rules out further delocalization in the molecule. In the crystal, C—H...F hydrogen bonds connect the molecules intoC11(6) chains along theaaxis. C—H...O hydrogen bonds form, which featureR22(12) loops and further connect these chains.

scholarly journals Crystal structure ofN′′-benzyl-N′′-[3-(benzyldimethylazaniumyl)propyl]-N,N,N′,N′-tetramethylguanidinium bis(tetraphenylborate)

2015 ◽  
Vol 71 (12) ◽  
pp. o1086-o1087
Author(s):  
Ioannis Tiritiris ◽  
Willi Kantlehner
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Positive Charge ◽  
Planar Geometry ◽  
Methyl Groups ◽  
Two Dimensional ◽  
Single Bond ◽  
Double Bond Character ◽  
Bond Lengths ◽  
Bond Character

In the crystal structure of the title salt, C24H38N42+·2C24H20B−, the C—N bond lengths in the central CN3unit of the guanidinium ion are 1.3364 (13), 1.3407 (13) and 1.3539 (13) Å, indicating partial double-bond character. The central C atom is bonded to the three N atoms in a nearly ideal trigonal–planar geometry and the positive charge is delocalized in the CN3plane. The bonds between the N atoms and the terminal methyl groups of the guanidinium moiety and the four C—N bonds to the central N atom of the (benzyldimethylazaniumyl)propyl group have single-bond character. In the crystal, C—H...π interactions between the guanidinium H atoms and the phenyl C atoms of the tetraphenylborate ions are present, leading to the formation of a two-dimensional supramolecular pattern parallel to theacplane.

THE SOLVOLYSIS OF THE ALPHA- AND BETA-3,4,6-TRI-O-ACETYL-D-GLUCOPYRANOSYL CHLORIDES

1955 ◽  
Vol 33 (1) ◽  
pp. 128-133 ◽  
Author(s):  
R. U. Lemieux ◽  
G. Huber
Keyword(s):  
Acetic Acid ◽  
Double Bond ◽  
Positive Charge ◽  
Main Reaction ◽  
Main Reaction Product ◽  
Double Bond Character ◽  
Ionic Reactions ◽  
Oxygen Bond ◽  
Bond Character ◽  
Anomeric Center

3,4,6-Tri-O-acetyl-β-D-glucopyranosyl chloride was found to undergo solvolysis in acetic acid to form 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose as the main reaction product. The much less reactive anomeric α-chloride also appeared to undergo solvolysis with extensive inversion of the anomeric center. It is submitted that the tendencies for inversion obtained in these ionic reactions are due to the conformations imposed on the intermediate ions through distribution of the positive charge to the ring oxygen and the consequent introduction of double-bond character to the carbon-1 to ring-oxygen bond.

scholarly journals 2-Dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-4,5-dihydroimidazolium tetraphenylborate

IUCrData ◽  
2016 ◽  
Vol 1 (1) ◽  
Author(s):  
Ioannis Tiritiris ◽  
Willi Kantlehner
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Positive Charge ◽  
Planar Geometry ◽  
Two Dimensional ◽  
Ethoxy Group ◽  
Double Bond Character ◽  
Bond Lengths ◽  
Phenyl Rings ◽  
Bond Character

In the crystal structure of the title salt, C10H20N3O2+·C24H20B−, the C—N bond lengths in the cation are 1.327 (3), 1.339 (3) and 1.342 (3) Å, indicating partial double-bond character. The central C atom is bonded to the three N atoms, indicating only a slight deviation from a trigonal–planar geometry. The positive charge is delocalized in the CN3plane. The ethoxy group is disordered over two orientations, with an occupancy ratio of 0.60 (1):0.40 (1). C—H...π interactions are present between the guanidinium H atoms and the phenyl C atoms of the tetraphenylborate ions. The phenyl rings form aromatic pockets, in which the cations are embedded. This leads to the formation of a two-dimensional supramolecular pattern along theacplane.

Synthesis and structure of 1,1,3,3,-tetramethyl-2-phenyl-2-(2′,6′-diphenyl-4′-pyrylio)-guanidinium diperchlorate

1994 ◽  
Vol 72 (2) ◽  
pp. 352-356 ◽  
Author(s):  
Wlodzimierz Galezowski ◽  
Pradip K. Bakshi ◽  
Kenneth T. Leffek ◽  
T. Stanley Cameron
Keyword(s):  
Double Bond ◽  
Carbon Atom ◽  
Perchloric Acid ◽  
Positive Charge ◽  
Monoclinic Space Group ◽  
Double Bond Character ◽  
Central Carbon ◽  
Guanidinium Cation ◽  
Bond Character ◽  
Positively Charged

The reaction of 2-N-phenyl-1,1,3,3-tetramethylguanidine with 2,6-diphenylpyran-4-one in the presence of phosphorus oxy-chloride, followed by treatment with perchloric acid, yields 1,1,3,3-tetramethyl-2-phenyl-2-(2′,6′-diphenyl-4′-pyrylio)guanidinium diperchlorate. Crystals of this material are monoclinic, space group P21/n, a = 14.535(3), b = 13.685(3), c = 23.579(7) Å, β = 140.38(2)°, R = 0.0633 based on 1691 observed reflections. The substitution of the positively charged pyrylio group on one of the three nitrogen atoms of the guanidinium cation disrupts the symmetry of the distribution of the positive charge on the nitrogen atoms. The two C—N bonds of the central carbon atom of the guanidinium ion to the two methylated nitrogen atoms show more double-bond character than that to the nitrogen carrying the pyrylio group.

scholarly journals Bis(μ-N,N-diallyldithiocarbamato)bis[(N,N-diallyldithiocarbamato)cadmium]

2017 ◽  
Vol 73 (9) ◽  
pp. 1353-1356 ◽  
Author(s):  
Damian C. Onwudiwe ◽  
Madalina Hrubaru ◽  
Eric C. Hosten ◽  
Charmaine Arderne
Keyword(s):  
Double Bond ◽  
Title Compound ◽  
Negative Charge ◽  
Planar Geometry ◽  
Double Bond Character ◽  
Square Planar ◽  
Bidentate Mode ◽  
Bond Character

The title compound, [Cd2(C7H10NS2)4], is a neutral dinuclear cadmium(II) complex bearing four bisN,N-diallyldithiocarbamate ligands coordinating to two CdIIcations. In each of the monomeric subunits, there are four S atoms of two dithiocarbamate ligands [Cd—S = 2.5558 (3), 2.8016 (3), 2.6050 (3) and 2.5709 (3) Å] that coordinate to one CdIIatom in a bidentate mode. The dimers are located over an inversion centre bridged by two additional bridging Cd—S bonds [2.6021 (3) Å], leading to a substantial distortion of the geometry of the monomeric subunit from the expected square-planar geometry. The five-coordinate environment around each of the CdIIions in the dimer is best described as substantially tetragonally distorted square pyramidal. The dithiocarbamate groups are themselves planar and are also coplanar with the CdIIions. The negative charge on these groups is delocalized by resonance across the S atoms bound to the CdIIcation. This delocalization of the π electrons in the dithiocarbamate groups also extends to the C—N bonds as they reveal significant double bond character [C—N = 1.3213 (16) and 1.3333 (15) Å].

scholarly journals N,N,N′,N′,N′′-Pentamethyl-N′′-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate)

2013 ◽  
Vol 69 (2) ◽  
pp. o292-o292 ◽  
Author(s):  
Ioannis Tiritiris
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Positive Charge ◽  
Planar Geometry ◽  
Methyl Groups ◽  
Single Bond ◽  
Double Bond Character ◽  
Bond Lengths ◽  
Phenyl Rings ◽  
Bond Character

In the crystal structure of the title salt, C12H30N42+·2C24H20B−, the C—N bond lengths in the central CN3unit of the guanidinium ion are 1.3388 (17), 1.3390 (16) and 1.3540 (17) Å, indicating partial double-bond character in each. The central C atom is bonded to the three N atoms in a nearly ideal trigonal-planar geometry and the positive charge is delocalized in the CN3plane. The bonds between the N atoms and the terminalC-methyl groups of the guanidinium moiety, all have values close to a typical single bond [1.4630 (16)–1.4697 (17) Å]. C—H...π interactions are present between the guanidinium H atoms and the phenyl C atoms of one tetraphenylborate ion. The phenyl rings form a kind of aromatic pocket, in which the guanidinium ion is embedded.

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