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Journal articles on the topic 'N-N bonds'

Author: Grafiati

Published: 27 February 2024

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1

Tiritiris, Ioannis, and Willi Kantlehner. "Crystal structure ofN-[3-(dimethylazaniumyl)propyl]-N′,N′,N′′,N′′-tetramethyl-N-(N,N,N′,N′-tetramethylformamidiniumyl)guanidinium dibromide hydroxide monohydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1078—o1079. http://dx.doi.org/10.1107/s2056989015024305.

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The asymmetric unit of the title hydrated salt, C15H37N63+·2Br−·OH−·H2O, contains one cation, three partial-occupancy bromide ions, one hydroxide ion and one water molecule. Refinement of the site-occupancy factors of the three disordered bromide ions converges with occupancies 0.701 (2), 0.831 (2) and 0.456 (2) summing to approximately two bromide ions per formula unit. The structure was refined as a two-component inversion twin with volume fractions 0.109 (8):0.891 (8) for the two domains. The central C3N unit of the bisamidinium ion is linked to the aliphatic propyl chain by a C—N single bond. The other two bonds in this unit have double-bond character as have the four C—N bonds to the outer NMe2groups. In contrast, the three C—N bonds to the central N atom of the (dimethylazaniumyl)propyl group have single-bond character. Delocalization of the two positive charges occurs in the N/C/N and C/N/C planes, while the third positive charge is localized on the dimethylammonium group. The crystal structure is stabilized by O—H...O, N—H...Br, O—H...Br and C—H...Br hydrogen bonds, forming a three-dimensional network.

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2

Ovchynnikov, Vladimir. "N,N′-Dimethyl-N′′-(trichloroacetyl)phosphoramide." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 9, 2013): o1759. http://dx.doi.org/10.1107/s1600536813030389.

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In the title compound, C4H9Cl3N3O2P or CCl3C(O)NHP(O)(NHCH3)2, the P atom has a strongly distorted tetrahedral geometry due to the formation of intermolecular strong hydrogen bonds involving the N atoms. In the crystal, N—H...O=P and N—H...O=C hydrogen bonds connect the molecules into a two-dimensional array parallel to (100). An intramolecular P...O contact [P...O = 2.975 (3) Å] is observed. The CCl3group is rotationally disordered, with occupancies of 0.60 (3) and 0.40 (3)

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3

Orea Flores, Ma Laura, Alberto Galindo Guzmán, Dino Gnecco Medina, and Sylvain Bernès. "N-Benzoyl-N,N′-dicyclohexylurea." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 21, 2006): o2922—o2923. http://dx.doi.org/10.1107/s1600536806022173.

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4

Karim, Alavi, Marcus Reitti, Anna-Carin C. Carlsson, Jürgen Gräfenstein, and Máté Erdélyi. "The nature of [N–Cl–N]+and [N–F–N]+halogen bonds in solution." Chem. Sci. 5, no. 8 (2014): 3226–33. http://dx.doi.org/10.1039/c4sc01175a.

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The solution symmetry of [N–Cl–N]⁺and [N–F–N]⁺halogen bonds is discussed, in comparison to the iodine and bromine-centered bonds as well as to the corresponding three-center [N–H–N]⁺hydrogen bond.

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5

Marek, Jaromír, Zdeněk Trávníček, and Šárka Čermáková. "(N,N,N′,N′′,N′′-Pentamethyldiethylenetriamine-κ3 N,N′,N′′)(trithiocyanurato-κ2 N,S)zinc(II)." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 14, 2007): m725—m727. http://dx.doi.org/10.1107/s1600536807006484.

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The structure of the title compound, [Zn(C9H23N3)(C3HN3S3)], consists of discrete molecules connected by N—H...S hydrogen bonds into centrosymmetric dimers. The ZnII atom is pentacoordinated in a deformed trigonal–bipyramidal geometry by three N atoms of a tridentate N,N,N′,N′′,N′′-pentamethyldiethylenetriamine ligand, and one S and one N atoms of a trithiocyanurate dianion bonded as a bidentate ligand. The crystal structure is further stabilized by close contacts of the types C—H...S and C—H...N.

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6

Spychała, Jarosław. "Stabilization of N-, N,N-, N,N′-methylated and unsubstituted simple amidine salts by multifurcated hydrogen bonds." Spectroscopy 20, no. 4 (2006): 169–76. http://dx.doi.org/10.1155/2006/589273.

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In the light of the usefulness of amidines in medicinal chemistry, this paper considers the effects on biological properties and chemical reactivities of organic molecules affected by intramolecular interactions. The study of chemical shifts has been an important source of information on the electronic structure of amidine salts and their ability to form non-covalent bonds with nucleic acids. The NMR and IR results demonstrate that hydrogen bonds are a force for promoting chemical reactions. The thymine O2 carbonyl oxygen in a close proximity to the amidinium cation does interact with the appropriately spaced amidinium NH donor moieties. The1H-15N 2D NMR (GHSQC and GHMBC) spectra with natural isotopic abundance of15N fully confirm the intramolecular character of the bonds. A rule able to estimate the relative strength of the new multifurcated hydrogen bonds is given. The appearance of the ΔδNHchemical shift differences near zero is due to the strong intramolecular interactions. The strength of the H-bond donation by acetamidines is reflected in the N–H dissociation/recombination process (positive charge shift has been invoked to explain other effects on benzamidines). The temperature dependence of chemical shift for the amidine NH protons in dimethyl sulfoxide solutions is herein discussed.

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7

Bardajee, Ghasem Rezanejad, Mitchell A. Winnik, and Alan J. Lough. "4-[N-(2-Hydroxyethyl)-N-methylamino]-N-isopropyl-1,8-naphthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 31, 2006): o1615—o1617. http://dx.doi.org/10.1107/s1600536806010294.

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In the title crystal structure, C18H20N2O3, molecules are linked into centrosymmetric dimers via O—H...O hydrogen bonds [H...O = 1.92 (3) Å]. These dimers are, in turn, linked by weak C—H...O hydrogen bonds [H...O = 2.42 Å], forming a two-dimensional network.

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8

Cai, Xiao-Qing, and Mao-Lin Hu. "N,N′,N′′-Tricyclohexylguanidinium chloride." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 8, 2006): o1260—o1261. http://dx.doi.org/10.1107/s1600536806007331.

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In the title crystal structure, C19H36N3 +·Cl−, the central C atom of the N,N′,N′′-tricyclohexylguanidinium ion and the chloride ion both lie on positions of site symmetry 3. Weak N—H...Cl hydrogen bonds [N...Cl = 3.539 (3) Å] link anions and cations, forming a three-dimensional network.

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9

Akhtar, Muhammad, Mohammed Fettouhi, Maqsood Ahmed, Islam Ullah Khan, and Saeed Ahmad. "N,N,N′,N′-Tetramethylethylenediammonium tetrachloridozincate." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (November 6, 2013): m642. http://dx.doi.org/10.1107/s1600536813029802.

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The asymmetric unit of the title compound, (C6H18N2)[ZnCl4], consists of one tetrachloridozincate anion and two half-N,N,N′N′-tetramethylethylenediammonium cations. Each of the two diammonium cations is located about an inversion center and one of them is disordered over two sets of sites in a 0.780 (17):0.220 (17) ratio. The ZnIIatom has a slightly distorted tetrahedral coordination environment. The cations and anions are connectedviaN—H...Cl hydrogen bonds into chains extending along [0-11].

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10

Tiritiris, Ioannis, and Willi Kantlehner. "Crystal structure ofN,N,N′,N′,N′′,N′′-hexamethylguanidinium cyanate 1.5-hydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1076—o1077. http://dx.doi.org/10.1107/s2056989015024317.

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The title hydrated salt, C7H18N3+·OCN−.1.5H2O, was synthesized starting fromN,N,N′,N′,N′′,N′′-hexamethylguanidinium chloride by a twofold anion-exchange reaction. The asymmetric unit contains two cations, two cyanate anions and three water molecules. One cation shows orientational disorder and two sets of N-atom positions were found related by a 60° rotation, with an occupancy ratio of 0.852 (6):0.148 (6). The C—N bond lengths in both guanidinium ions range from 1.329 (2) to 1.358 (10) Å, indicating double-bond character, pointing towards charge delocalization within the NCN planes. Strong O—H...N hydrogen bonds between the crystal water molecules and the cyanate ions and strong O—H...O hydrogen bonds between the water molecules are present, resulting in a two-dimensional hydrogen bonded network running parallel to the (001) plane. The hexamethylguanidinium ions are packed in between the layers built up by water molecules and cyanate ions.

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11

Razis, S. Aminah A., M. Sukeri M. Yusof, A. Maisara Kadir, and Bohari M. Yamin. "N-(4-Methylbenzoyl)-N′-(4-methylphenyl)thiourea." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 24, 2007): o4395. http://dx.doi.org/10.1107/s1600536807049720.

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The title compound, C16H16N2OS, adopts a trans–cis configuration of the 4-methylbenzoyl and 4-methylphenyl groups, with respect to the thiono S atom across the thiourea C—N bonds. The dihedral angle between the two groups is 10.36 (8)°. The structure is stabilized by intermolecular hydrogen bonds which form dimers. There are also intramolecular hydrogen bonds.

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12

Pereira Silva, P. S., J. A. Paixão, M. Ramos Silva, and A. Matos Beja. "N,N′,N′′′-Triphenylguanidinium nitrate." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 28, 2006): o3073—o3075. http://dx.doi.org/10.1107/s1600536806024068.

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The title salt, C19H18N3 +·NO3 −, has two symmetry-independent cations and two symmetry-independent anions in the asymmetric unit, with almost identical geometries. Bond lengths and angles within the guanidinium unit are close to those expected for a Csp 2 atom. Intermolecular hydrogen bonds link anions and cations, forming chains that run along the c axis.

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13

Tiritiris, Ioannis, Wolfgang Frey, and Willi Kantlehner. "N′′-(4-Methoxyphenyl)-N,N,N′-trimethyl-N′-phenylguanidine." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (March 22, 2014): o460. http://dx.doi.org/10.1107/s1600536814005819.

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In the title compound, C17H21N3O, the C—N bond lengths in the guanidine unit are 1.2889 (19), 1.3682 (19) and 1.408 (2) Å, indicating double- and single-bond character. The N—C—N angles are 115.10 (13), 119.29 (15) and 125.61 (14)°, showing a deviation of the CN3plane from an ideal trigonal–planar geometry. In the crystal, non-classical C—H...O hydrogen bonds between methyl H atoms and methoxy O atoms are present, generating centrosymmetric dimers running in the [101] direction.

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14

Münchenberg, Jochen, Holger Thönnessen, Peter G. Jones, and Reinhard Schmutzler. "Synthese von Organylphosphonigsäure-N-(N′,N′,N″,N″-tetramethyl)guanidinidfluoriden und ihre Reaktion mit Chalkogenen und Triphenylmethylazid; Darstellung und Charakterisierung von Organylchalkogeno- und Phenyltriphenylmethylimino- phosphonsäure-N-(N′,N′,N″,N″-tetramethyl)guanidinidfluoriden / Synthesis of Organophosphonous-N-(N′,N′,N″,N″-tetramethyl)guanidinide Fluorides and their Reaction with Chalcogens and Triphenylmethyl Azide; Synthesis and Characterization of Organochalcogeno- and Phenyltriphenylmethylimino-phosphonic-N-(N′,N′,N″,N″-tetramethyl)-guanidinide Fluorides." Zeitschrift für Naturforschung B 51, no. 8 (August 1, 1996): 1150–60. http://dx.doi.org/10.1515/znb-1996-0816.

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The organophosphonous-N-(N′,N′,N″,N″-tetramethyl)guanidinide fluorides RP(F)N=C(NMe2)2 2a (R = t-Bu) and 2b (R = Ph) were synthesized. They are readily oxidized by the urea-H2O2 1:1 adduct and by elemental sulfur, selenium and tellurium to give the compounds 4a/b, 5a/b, 6a/b and 7a/b respectively. Compound 2b undergoes a Staudinger reaction with triphenylmethyl azide to yield the phosphine imide 3. The compounds were characterized by 1H-, 13C-, 19F and 31P NMR spectroscopy, and 6a/b and 7a/b by 77Se and 125Te NMR spectroscopy. The structures of the sulfur compound 5b and the selenium compound 6a were confirmed by X-ray crystal structure analysis. Both molecules exhibit short P-N-bonds [158.9(2) pm and 159.8(3) pm] consistent with partial double bond character even though the P(:S) and the P(:Se) bonds are not longer than a normal double bond.

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15

Tiritiris, Ioannis, and Willi Kantlehner. "Crystal structure ofN′′-benzyl-N′′-[3-(benzyldimethylazaniumyl)propyl]-N,N,N′,N′-tetramethylguanidinium bis(tetraphenylborate)." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1086—o1087. http://dx.doi.org/10.1107/s2056989015024639.

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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.

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16

Sun, Chuan-Wen, and Xiao-Dong Zhang. "N-Benzoyl-N′-(tert-butylaminocarbonyl)thiourea." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 9, 2006): o2700—o2701. http://dx.doi.org/10.1107/s1600536806019799.

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The asymmetric unit of the title compound, C13H17N3O2, contains two molecules and neither of them adopts a planar conformation. The crystal structure is stabilized by the intermolecular N—H...O and intramolecular N—H...O and N—H...S hydrogen bonds. The intermolecular hydrogen bonds link the molecules to form infinite chains along the b axis.

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17

Tiritiris, Ioannis, and Willi Kantlehner. "N,N,N′,N′-Tetramethyl-N′′,N′′-dipropylguanidinium chloride–(2Z)-2,3-diaminobut-2-enedinitrile (1/1)." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 31, 2012): o1944. http://dx.doi.org/10.1107/s1600536812023264.

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In the crystal structure of the title compound, C11H26N3 +·Cl−·C4H4N4, the (2Z)-2,3-diaminobut-2-ene-dinitrile (Z-DAMN) molecules are connected with the chloride ions via N—H...Cl hydrogen bonds, forming ribbons running along the a axis. The guanidinium ions are located in between the ribbons formed by Z-DAMN molecules and chloride ions.

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18

Said, Farouq F., Basem F. Ali, Darrin Richeson, and Ilia Korobkov. "Bis(N,N′,N′′-triisopropylguanidinium) fumarate–fumaric acid (1/1)." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 26, 2012): o1906. http://dx.doi.org/10.1107/s1600536812023094.

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The asymmetric unit of the title compound, C10H24N3 +·0.5C4H2O4 2−·0.5C4H4O4, comprises a triisopropylguanidinium cation, half of a fumarate dianion and half of a fumaric acid molecule; both the fumarate dianion and the fumaric acid molecule are located on inversion centres. In the crystal, intermolecular O—H...O hydrogen bonds between the carboxyl groups of the fumaric acid molecules and the carboxylate groups of the fumarate anions lead to the formation of a hydrogen-bonded supramolecular twisted chain along the b axis. The triisopropylguanidinium cations interact with the fumarate–fumaric acid chains via extensive N—H...O and C—H...O hydrogen bonds, leading to a ladder arrangement, with the cation being the rungs that bridge three curled chains of fumarate–fumaric acid. The crystal packing is stabilized by N—H...O and C—H...O (cation...fumarate/fumaric) and O—H...O (fumarate...fumaric) hydrogen bonds, consolidating a three-dimensional network.

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19

Onwudiwe, Damian C., Madalina Hrubaru, Eric C. Hosten, and Charmaine Arderne. "Bis(μ-N,N-diallyldithiocarbamato)bis[(N,N-diallyldithiocarbamato)cadmium]." Acta Crystallographica Section E Crystallographic Communications 73, no. 9 (August 21, 2017): 1353–56. http://dx.doi.org/10.1107/s2056989017011616.

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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].

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20

Gasser, Gilles, and Helen Stoeckli-Evans. "N-Benzoyl-N-(2-pyridylcarbonyl)benzamide." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 28, 2007): o1518—o1520. http://dx.doi.org/10.1107/s1600536807008884.

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The molecule of the title compound, C20H14N2O3, a tertiary amine with one 2-pyridylcarbonyl and two benzamide substituents, is shaped like a propeller. In the crystal structure, molecules related by a center of symmetry are linked by C—H...O hydrogen bonds to form dimers. These dimers are linked by two further translationally related C—H...O hydrogen bonds and a C—H...π interaction, forming chains extending in the a-axis direction.

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21

Tiritiris, Ioannis, Wolfgang Frey, and Willi Kantlehner. "N,N,N′-Trimethyl-N′′-(4-nitrophenyl)-N′-phenylguanidine." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 5, 2014): o516—o517. http://dx.doi.org/10.1107/s160053681400693x.

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The C—N bond lengths in the guanidine unit of the title compound, C16H18N4O2, are 1.298 (2), 1.353 (2) and 1.401 (3) Å, indicating double- and single-bond character. The N—C—N angles are 115.81 (16), 118.90 (18) and 125.16 (18)°, showing a deviation of the CN3plane from an ideal trigonal–planar geometry. In the crystal, C—H...O hydrogen bonds are observed between the methyl- and aromatic-H atoms and nitro-O atoms. One H atom of the phenyl ring and of the NMe2group associate with the O atoms of the nitro group, giving chains along thea-andb-axis directions. Cross-linking of these two chains results in a two-dimensional network alongbc.

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22

Bedin, Michele, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, et al. "Counterion influence on the N–I–N halogen bond." Chemical Science 6, no. 7 (2015): 3746–56. http://dx.doi.org/10.1039/c5sc01053e.

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23

Razis, S. Aminah A., M. Sukeri M. Yusof, and Bohari M. Yamin. "N-(4-Methoxyphenyl)-N′-(4-methylbenzoyl)thiourea." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 3, 2007): o4225. http://dx.doi.org/10.1107/s1600536807047551.

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In the title compound, C16H16N2O2S, one of the C—N bonds adopts a transoid configuration, whereas the other C—N bond is cisoid configured. The molecular conformation is stabilized by an intramolecular N—H...O hydrogen bond, and the crystal packing is stabilized by intermolecular N—H...S and C—H...O hydrogen bonds, forming chains parallel to the a axis.

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24

Song, Hui-Hua, and Bao-Qing Ma. "trans-4,4′-Azopyridine N,N′-dioxide dihydrochloride." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 16, 2007): o1332—o1333. http://dx.doi.org/10.1107/s1600536807006630.

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The title compound is a salt, trans-1,1′-dihydroxy-4,4′-diazenediyldipyridinium dichloride, C10H10N4O2 2+·2C l−, in which the trans-4,4′-azopyridine N,N′-dioxide cation is located on an inversion centre with the pyridine N-oxide atoms protonated. The Cl− anions form strong hydrogen bonds to these H atoms. Weak C—H...Cl hydrogen bonds link the cations and anions into a two-dimensional sheet.

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25

Ndiaye, Mamadou, Abdoulaye Samb, Libasse Diop, and Thierry Maris. "Crystal structure of bis(N,N,N′,N′-tetramethylguanidinium) tetrachloridocuprate(II)." Acta Crystallographica Section E Crystallographic Communications 72, no. 7 (June 24, 2016): 1047–49. http://dx.doi.org/10.1107/s2056989016010161.

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In the structure of the title salt, (C5H14N3)2[CuCl4], the CuIIatom in the anion lies on a twofold rotation axis. The tetrachloridocuprate(II) anion adopts a flattened tetrahedral coordination environment and interacts electrostatically with the tetramethylguanidinium cation. The crystal packing is additionally consolidated through N—H...Cl and C—H...Cl hydrogen bonds, resulting in a three-dimensional network structure.

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26

Hassan, N. Norainun N., Maisara A. Kadir, M. Sukeri M. Yusof, and Bohari M. Yamin. "N-(2-Furoyl)-N′-(6-methyl-2-pyridyl)thiourea." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 3, 2007): o4224. http://dx.doi.org/10.1107/s1600536807047265.

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The title molecule, C12H11N3O2S, adopts a cis–trans configuration of the furoyl and 6-methyl-2-pyridyl groups with respect to the thiono S atom across the thiourea C—N bonds. Intramolecular N—H...O, N—H...N and C—H...O hydrogen bonds contribute to the essential planarity of the molecular skeleton. In the crystal structure, weak intermolecular N—H...S hydrogen bonds link the molecules into centrosymmetric dimers.

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27

Bolotin, Dmitrii S., Nadezha A. Bokach, and Matti Haukka. "Dichlorido[N-(N,N-dimethylcarbamimidoyl)-N′,N′,4-trimethylbenzohydrazonamide]platinum(II) nitromethane hemisolvate." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (March 12, 2014): m131—m132. http://dx.doi.org/10.1107/s1600536814003894.

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In the title compound, [PtCl2(C13H21N5)]·0.5CH3NO2, the PtIIatom is coordinated in a slightly distorted square-planar geometry by two Cl atoms and two N atoms of the bidentate ligand. The (1,3,5-triazapentadiene)PtIImetalla ring is slightly bent and does not conjugate with the aromatic ring. In the crystal, N—H...Cl hydrogen bonds link the complex molecules, forming chains along [001]. The nitromethane solvent molecule shows half-occupancy and is disordered over two sets of sites about an inversion centre.

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28

Podda, Enrico, Eleanor Dodd, Massimiliano Arca, M. Carla Aragoni, Vito Lippolis, Simon J. Coles, and Anna Pintus. "N,N′-Dipropyloxamide." Molbank 2024, no. 1 (December 22, 2023): M1753. http://dx.doi.org/10.3390/m1753.

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N,N′-Dipropyloxamide (1) was synthesised by the reaction between diethyloxalate and n-propylamine in ethanol. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single crystal X-ray diffraction were isolated by the slow evaporation of a methyl alcohol solution of the compound. The resulting crystal structure shows the prominent role exerted by intermolecular hydrogen bonds in the crystal packing.

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29

Tiritiris, Ioannis, and Willi Kantlehner. "Crystal structure ofN-[3-(dimethylamino)propyl]-N′,N′,N′′,N′′-tetramethyl-N-(N,N,N′,N′-tetramethylformamidiniumyl)guanidinium bis(tetraphenylborate)." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1045—o1046. http://dx.doi.org/10.1107/s2056989015023336.

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In the title salt, C15H36N62+·2C24H20B−, the three N—C bond lengths in the central C3N unit of the bisamidinium ion range between 1.388 (3) and 1.506 (3) Å, indicating single- and double-bond character. Furthermore, four C—N bonds have double-bond character. Here, the bond lengths range from 1.319 (3) to 1.333 (3) Å. Delocalization of the positive charges occurs in the N/C/N and C/N/C planes. The dihedral angle between both N/C/N planes is 70.5 (2)°. In the crystal, C—H...π interactions between H atoms of the cation and the benzene rings of both tetraphenylborate ions are present. The benzene rings form aromatic pockets, in which the bisamidinium ion is embedded. This leads to the formation of a two-dimensional supramolecular pattern along theabplane.

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30

Tabey, Alexis, Pooja Y. Vemuri, and Frederic W. Patureau. "Cross-dehydrogenative N–N couplings." Chemical Science 12, no. 43 (2021): 14343–52. http://dx.doi.org/10.1039/d1sc03851f.

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For more than a century, the dehydrogenative formation of N–N bonds has remained mostly confidential. Several cross-dehydrogenative N–N coupling methods have appeared recently, promising a soon to come broad applicability of the concept.

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31

Zareef, Muhammad, Rashid Iqbal, Javid H. Zaidi, Muhammad Arfan, and Masood Parvez. "N-Benzoyl-N′-methyl-N′-(p-tolylsulfonyl)hydrazine." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 28, 2006): o3049—o3051. http://dx.doi.org/10.1107/s1600536806023877.

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The crystal structure of the title compound, C15H16N2O3S, contains chains running along the a axis which are formed via intermolecular N—H...O hydrogen bonds. The side chain comprising the N–N–C(=O)–C sequence of atoms is planar to within 0.0172 (14) Å and the benzene rings are inclined at 33.09 (11)° to one another.

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32

Ren, Guang-Ming, Dong-Lin Shang, and Jian-Ping Guo. "Bis{μ-N-[(N,N-dimethylamino)dimethylsilyl]-2,6-dimethylanilido}lithium(I)." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 21, 2007): m793—m794. http://dx.doi.org/10.1107/s1600536807006460.

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33

Shin, Jong Won, and Kil Sik Min. "N,N,N′,N′-Tetrakis(pyridin-4-yl)methanediamine monohydrate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 2, 2012): o1600. http://dx.doi.org/10.1107/s1600536812019010.

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In the title compound, C21H18N6·H2O, two 4,4′-dipyridylamine groups are linked by a methylene C atom, which sits on a twofold axis. The lattice water molecule is located slightly off a twofold axis, and is therefore disordered over two positions. In the crystal, the organic molecules and the water molecule are linked by O—H...N hydrogen bonds. The organic molecules exhibit extensive offset face-to-face π–π interactions to symmetry equivalents [centroid–centroid distances = 3.725 (3) and 4.059 (3) Å].

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34

Tobón-Trujillo, Luis Manuel, Luis Felipe Villanueva-Sánchez, Diego Martínez-Otero, and Alejandro Dorazco-González. "Crystal structure of bis(μ2-tetrabromophthalato-κ2O1:O2)bis[aqua(N,N,N′,N′-tetramethylethane-1,2-diamine-κ2N,N′)copper(II)]." Acta Crystallographica Section E Crystallographic Communications 71, no. 9 (August 22, 2015): m171—m172. http://dx.doi.org/10.1107/s2056989015015194.

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In the title complex, [Cu2(C8Br4O4)2(C6H16N2)2(H2O)2], the CuIIcation is chelated by a tetramethylethane-1,2-diamine ligand and coordinated by a water molecule as well as bridged by two tetrabromophthalate anions in a distorted O3N2trigonal–bipyramidal geometry. The two symmetry-related tetrabromophthalate anions bridge the two CuIIcations, forming a centrosymmetric dinuclear complex in which the Cu...Cu separation is 5.054 (2) Å. Intramolecular classic O—H...O hydrogen bonds and weak C—H...O hydrogen bonds occur in the dinuclear molecule. In the crystal, the molecules are linked by weak C—H...Br and C—H...O interactions into supramolecular chains propagating along theb-axis direction.

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35

Tiritiris, Ioannis, and Willi Kantlehner. "3-Phenyl-N,N,N′,N′-tetramethyl-1-ethyne-1-carboximidamidium bromide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 19, 2012): o1812. http://dx.doi.org/10.1107/s1600536812021873.

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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.

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36

Tiritiris, Ioannis. "N,N,N′,N′,N′′-Pentamethyl-N′′-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate)." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (January 26, 2013): o292. http://dx.doi.org/10.1107/s1600536813001992.

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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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37

Zhao, Weizhe, Jiali Xu, Fan Yang, and Xianghua Zeng. "Advances on the Synthesis of N—N Bonds." Chinese Journal of Organic Chemistry 42, no. 5 (2022): 1336. http://dx.doi.org/10.6023/cjoc202111019.

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38

Ding, Keying, Aaron W. Pierpont, William W. Brennessel, Gudrun Lukat-Rodgers, Kenton R. Rodgers, Thomas R. Cundari, Eckhard Bill, and Patrick L. Holland. "Cobalt−Dinitrogen Complexes with Weakened N−N Bonds." Journal of the American Chemical Society 131, no. 27 (July 15, 2009): 9471–72. http://dx.doi.org/10.1021/ja808783u.

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39

Puttreddy, Rakesh, Ondřej Jurček, Sandip Bhowmik, Toni Mäkelä, and Kari Rissanen. "Very strong −N–X+⋯−O–N+ halogen bonds." Chemical Communications 52, no. 11 (2016): 2338–41. http://dx.doi.org/10.1039/c5cc09487a.

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40

Tripathi, Garima, Khalid Badi-uz-zama, and Gurunath Ramanathan. "N…N pnicogen bonds in Boc-DOPA-OMe." Chemical Physics Letters 653 (June 2016): 117–21. http://dx.doi.org/10.1016/j.cplett.2016.04.076.

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41

Chandrasekhar, S., Ch Raji Reddy, and R. Jagadeeshwar Rao. "Unprecedented Direct Conversion of N-N and N=N bonds to N-(tert-Butyloxy)-carbamates." Synlett 2001, no. 10 (2001): 1561–62. http://dx.doi.org/10.1055/s-2001-17439.

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42

Xu, Tong-Tao, Xing-You Xu, Da-Qi Wang, Jian Gao, and Lu-De Lu. "[N,N,N′-Tris(3-aminopropyl)ethylenediamine-κ5 N]nickel bis(perchlorate)." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 30, 2006): m1713—m1715. http://dx.doi.org/10.1107/s1600536806024330.

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The asymmetric unit of the title complex, [Ni(C11H29N5)](ClO4)2, consists of an [Ni(C11H29N5)]2+ cation and two uncoordinated perchlorate anions. The NiII atom is five-coordinated in a slightly distorted square-pyramidal geometry, with four of the N atoms forming the basal plane and the fifth N atom in the apical position. The complex shows a three-dimensional network structure assembled by intermolecular hydrogen bonds.

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43

da Silva, Luiz Everson, Antonio Carlos Joussef, Sabine Foro, and Boris Schmidt. "Bis[4-n-propyl-N-(8-quinolyl)benzenesulfonamidato-κ2 N,N′]zinc(II) dimethylformamide solvate." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (April 11, 2006): m999—m1001. http://dx.doi.org/10.1107/s1600536806012414.

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In the title compound, [Zn(C18H17N2O2S)2]·C3H7NO, the Zn atom is four-coordinated by the N atoms of sulfonamide and quinoline groups. Two intermolecular C—H...O hydrogen bonds connect the molecules into a three-dimensional network.

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44

Yusof, M. Sukeri M., Norfazila M. Ariff, Maisara A. Kadir, and Bohari M. Yamin. "N-(2,5-Dichlorophenyl)-N′-isobutyrylthiourea." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 7, 2007): o1215—o1216. http://dx.doi.org/10.1107/s160053680700517x.

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The title compound, C11H12Cl2N2OS, adopts a trans–cis configuration of the isobutyryl and 2,5-dichlorophenyl groups with respect to the thiono S atom, across the thiourea C—N bonds. The crystal structure is stabilized by intermolecular N—H...S hydrogen bonding, forming dimers parallel to the ac plane.

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45

Klepetářová, Blanka, Emanuel Makrlík, Vasily A. Babain, and Václav Kašička. "N,N′-Diethyl-N,N′-diphenylpyridine-2,6-dicarboxamide." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 17, 2012): o1099—o1100. http://dx.doi.org/10.1107/s1600536812009026.

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The asymmetric unit of the title compound, C23H23N3O2, contains two molecules in both of which, one amide N atom is in asynposition with respect to the pyridine N atom, while the other amide N atom is in anantiposition (thesyn--anticonformation). There are minor conformational differences between the two molecules, as reflected in the Npyridine—C—C—Namidetorsion angles of −44.9 (3) and 136.0 (2)° for one molecule and 43.5 (3) and −131.1 (2)° for the other molecule. However, the two molecules show significant differences in the orientation of an ethyl group, with corresponding C—C—N—C torsion angles of 86.6 (3)° for one molecule and 79.6 (3)° for the other molecule. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming a three-dimensional supramolecular network.

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46

Zhou, Li-Ming, Guang-Hui Sun, Li-Jun Gao, Shao-Ming Fang, and Wei-Dong Yan. "Trichlorido(N,N-dimethylformamide-κO)bis(1,10-phenanthroline-κ2 N,N′)lanthanum(III) N,N-dimethylformamide disolvate." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 3, 2007): m2637—m2638. http://dx.doi.org/10.1107/s1600536807046739.

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In the title compound, [LaCl3(C12H8N2)2(C3H7NO)]·2C3H7NO, the LaIII ion is eight-coordinated by four N donors from two 1,10-phenanthroline ligands, one O atom from one N,N-dimethylformamide molecule and three chloride anions. In the crystal structure, the LaIII mononuclear units are linked to form a chain along the a axis by weak C—H...Cl hydrogen bonds. The chains are crosslinked to form a two-dimensional network parallel to the ab plane by π–π stacking interactions between the phen rings [centroid–centroid seperations range from 3.589 (2) to 3.708 (2) Å].

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47

Farrell, Dorcas M. M., Christopher Glidewell, John N. Low, Janet M. S. Skakle, and Choudhury M. Zakaria. "Polymorphs and pseudopolymorphs of N,N′-dithiobisphthalimide." Acta Crystallographica Section B Structural Science 58, no. 2 (March 25, 2002): 289–99. http://dx.doi.org/10.1107/s0108768101020006.

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N,N′-Dithiobisphthalimide, C16H8N2O4S2 (I), forms a wide range of polymorphs and solvates (pseudopolymorphs). When (I) is crystallized from methanol it yields a solvent-free polymorph (4), in Pna21 with Z′ = 1, in which the molecules are linked into chains by a single C—H...O hydrogen bond: crystallization from either acetonitrile or dimethylformamide produces a monoclinic polymorph (5), in P21/c with Z′ = 2, also solvent-free, in which the molecules are linked into molecular ladders. Nitromethane forms a monosolvate, C16H8N2O4S2·CH3NO2 (6), in P21/c with Z′ = 1, in which the solvent molecules are linked to the molecules of (I) not only via a conventional C—H...O hydrogen bond but also via a polarized multicentre interaction involving all three C—H bonds of the solvent molecule. Chlorobenzene forms a precise hemisolvate, C16H8N2O4S2·0.5C6H5Cl (7), in P{\bar 1 } with Z′ = 1, while ethylbenzene forms an approximate hemisolvate 2C16H8N2O4S2·0.913C6H5C2H5·0.087H2O (8), in P21/c with eight molecules of (I) per unit cell. In both solvates the molecules of (I) are linked, in (7) by π...π stacking interactions augmented by weak C—H...O hydrogen bonds and in (8) by stronger C—H...O hydrogen bonds: the solvent molecules lie in isolated cavities, disordered across inversion centres in (7) and fully ordered in general positions in (8). Crystallization of (I) either from tetrahydrofuran or from wet tert-butanol yields isomorphous solvates (9) and (10), respectively, in C2/c with Z′ = 0.5, in which molecules of (I) lie across twofold rotation axes and are linked by π...π stacking interactions and very weak C—H...O hydrogen bonds, forming a framework enclosing continuous channels: highly disordered solvent molecules lie within these channels. p-Xylene and toluene form isomorphous hemisolvates (11) and (12) with unit cells metrically very similar to those of (9) and (10), but in P21/n with Z′ = 1: in these two solvates the molecules of (I) are linked into a framework by very short C—H...O hydrogen bonds; the solvent molecules lie within continuous channels, but they are localized across inversion centres so that the toluene is disordered across an inversion centre.

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48

Wen, Yong-Hong, Li-Li Xu, Xue-Mei Li, and Shu-Sheng Zhang. "N,N′-Bis(2-ethoxyphenyl)oxamide." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 9, 2006): o2592—o2593. http://dx.doi.org/10.1107/s1600536806019623.

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49

Yusof, M. Sukeri M., Fatin Salbiah M. Asroh, Maisara A. Kadir, and Bohari M. Yamin. "N-(3-Methylbutyryl)-N′-phenylthiourea." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 7, 2007): o1190—o1191. http://dx.doi.org/10.1107/s1600536807001900.

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The title compound, C12H16N2OS, adopts a trans–cis configuration of the 3-methylbutyryl and phenyl groups, respectively, with respect to the thiono S atom, across the thiourea C—N bonds. An intramolecular N—H...O hydrogen bond is formed and intermolecular N—H...O and N—H...S interactions link the molecules into a two-dimensional network.

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50

Dieterich, Susanne, and Joachim Strähle. "Zur Struktur des Pentaazadienidions [tol-N=N-N-N=N-tol]-. Synthese und Kristallstruktur von Cs2(18-Krone-6)(tolN5tol)2 und (NH4)[Cr(NH3)6(H2O)4](tolN5tol)4 / The Structure of the Pentaazadienide Anion [tol-N=N—N—N=N-tol]-. Synthesis and Crystal Structure of Cs2(18-Crown-6)(tolN5tol)2 and (NH4)[Cr(NH3)6(H2O)4](tolN5tol)4." Zeitschrift für Naturforschung B 48, no. 11 (November 1, 1993): 1574–80. http://dx.doi.org/10.1515/znb-1993-1116.

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A concentrated solution of CsCI, 18-crown-6, and tol-N=N—N(H)—N=N-tol in aqueous ammonia affords Cs2(18-crown-6)(tolN5tol)2, which crystallizes in the triclinic space group P1̄ with a = 852.6(2), b = 1139.4(3), c = 1373.9(4) pm, α = 104.17(3), ß = 95.94(2), γ = 110.74(2)°, Ζ = 1. In the structure centrosymmetrical [Cs2(18-crown-6)]2+ moieties are packed with pairs of 1,5-bis(tolyl)pentaazadienide anions to built up columns along [100]. The N—N distances N1 —N2 = 128 pm and N4—N5 = 129 pm in the pentaazadienide anions indicate localized double bonds, while the distances N2—N3 and N3—N4 of 134 pm can be assigned to single bonds. A mixture of Cr(NH3)63+ and tolNNN(H)NNtol in concentrated aqueous ammonia yields triclinic (NH4)[Cr(NH3)6(H2O)4](tolN5tol)4 crystallizing in the space group P l with the lattice parameters a = 1561.1(1), b = 1619.3(3), c = 1703.3(2) pm, α = 107.03(1), β = 116.81(1), γ = 101.75(1)°, Ζ = 2. The structure contains tolN5tol- anions, NH4+ cations and [Cr(NH3)6(H2O)4]3+ complexes in which four triangular faces of the Cr(NH3)6 octahedron are capped by water molecules which are linked via hydrogen bonds. Within the pentaazadienide anions which are connected with the [Cr(NH3)6(H2O)4]3+ complexes also via hydrogen bonds an indication for localized double bonds Ν1=Ν2 and N4=N 5 has been obtained.

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