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Journal articles on the topic 'C-N bond forming'

Author: Grafiati

Published: 18 May 2024

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1

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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2

Frey, Johanna, Sabine Choppin, Françoise Colobert, and Joanna Wencel-Delord. "Towards Atropoenantiopure N–C Axially Chiral Compounds via Stereoselective C–N Bond Formation." CHIMIA International Journal for Chemistry 74, no. 11 (November 25, 2020): 883–89. http://dx.doi.org/10.2533/chimia.2020.883.

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N–C axial chirality, although disregarded for decades, is an interesting type of chirality with appealing applications in medicinal chemistry and agrochemistry. However, atroposelective synthesis of optically pure compounds is extremely challenging and only a limited number of synthetic routes have been designed. In particular, asymmetric N-arylation reactions allowing atroposelective N–C bond forming events remain scarce, although great advances have been achieved recently. In this minireview we summarize the synthetic approaches towards synthesis of N–C axially chiral compounds via stereocontrolled N–C bond forming events. Both organo-catalyzed and metal-catalyzed transformations are described, thus illustrating the diversity and specificity of both strategies.

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3

Shen, Hao, and Zuowei Xie. "Titanacarborane mediated C–N bond forming/breaking reactions." Journal of Organometallic Chemistry 694, no. 11 (May 2009): 1652–57. http://dx.doi.org/10.1016/j.jorganchem.2008.11.010.

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4

Liu, Yang, Zhongyi Mao, Alexandre Pradal, Pei-Qiang Huang, Julie Oble, and Giovanni Poli. "Palladium-Catalyzed [3 + 2]-C–C/N–C Bond-Forming Annulation." Organic Letters 20, no. 13 (June 13, 2018): 4057–61. http://dx.doi.org/10.1021/acs.orglett.8b01616.

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5

Li, Wei, Ruchun Yang, and Qiang Xiao. "(2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (January 8, 2014): o120. http://dx.doi.org/10.1107/s1600536813034995.

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The title compound, C11H12FIN4O3, is composed of a 7-carbapurine moiety connectedviaan N atom to 2-deoxy-2-fluoro-β-D-ribose. The conformation about the N-glycosydic bond is −antiwith χ = −129.0 (11)°. The glycosydic N—C bond length is 1.435 (14) Å. The sugar ring adopts anNconformation with an unsymmetrical twist O-endo-C-exo (oT4). The conformation around the C—C bond is +sc, with a torsion angle of 53.0 (12)°. In the crystal, molecules are linked by N—H...O hydrogen bonds, forming chains propagating along theaaxis. These chains are linkedviaO—H...I and C—H...O hydrogen bonds, forming layers lying parallel to thecaxis.

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6

Chkirate, Karim, Sevgi Kansiz, Khalid Karrouchi, Joel T. Mague, Necmi Dege, and El Mokhtar Essassi. "Crystal structure and Hirshfeld surface analysis of N-{2-[(E)-(4-methylbenzylidene)amino]phenyl}-2-(5-methyl-1-H-pyrazol-3-yl)acetamide hemihydrate." Acta Crystallographica Section E Crystallographic Communications 75, no. 2 (January 8, 2019): 154–58. http://dx.doi.org/10.1107/s2056989018017747.

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The asymmetric unit of the title compound, C20H20N4O·0.5H2O, contains two independent organic molecules (1 and 2) and a water molecule of crystallization. The two molecules differ primarily in the dihedral angles between the aromatic rings, which are 7.79 (7) and 29.89 (7)° in molecules 1 and 2, respectively. In each molecule there is intramolecular C—H...O hydrogen bond forming an S(6) ring motif. In molecule 1 there is an intramolecular N—H...π(pyrazole) interaction and an intramolecular C—H...π(pyrazole) interaction present. Molecule 1 is linked to molecule 2 by a C—H...π(benzene ring) interaction. An intramolecular N—H...N hydrogen bond and an intramolecular C—H...N hydrogen bond are also present in molecule 2. In the crystal, the three components are linked by Owater—H...N, N—H...Owater and N—H...N hydrogen bonds, forming chains along the [100] direction. The chains are linked by C—H...O and C—H...N hydrogen bonds, forming layers parallel to the ab plane. Finally, the layers are linked by C—H...π interactions, forming a three-dimensional structure.

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7

Mague, Joel T., Alaa A. M. Abdel-Aziz, Adel S. El-Azab, and Amer M. Alanazi. "1-Acetyl-5-methoxy-4-(phenylsulfanyl)imidazolidin-2-one." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (January 15, 2014): o145—o146. http://dx.doi.org/10.1107/s1600536814000117.

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The title compound, C12H14N2O3S, crystallizes with two independent molecules (AandB) in the asymmetric unit. The five-membered imidazolidin-2-one rings in both molecules are twisted about the C—C bond. In the crystal, theAandBmolecules are associatedviapairs of N—H...O hydrogen bonds, formingA–Bdimers. These dimers are linkedviaC—H...S hydrogen bonds, forming double dimers, which are in turn linkedviaC—H...O hydrogen bonds forming two-dimensional networks lying parallel to (001). There are also C—H...π interactions present, which consolide the layers and link them, so forming a three-dimensional structure.

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8

Fujii, Isao. "Crystal structure of (S)-2-amino-2-methylsuccinic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 12, 2015): o731—o732. http://dx.doi.org/10.1107/s2056989015016709.

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The title compound, C5H9NO4, crystallized as a zwitterion. There is an intramolecular N—H...O hydrogen bond involving thetrans-succinic acid and the ammonium group, forming anS(6) ring motif. In the crystal, molecules are linked by O—H...O hydrogen bonds, formingC(7) chains along thec-axis direction. The chains are linked by N—H...O and C—H...O hydrogen bonds, forming sheets parallel to thebcplane. Further N—H...O hydrogen bonds link the sheets to form a three-dimensional framework.

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9

Valdés, Carlos, Raquel Barroso, and María Cabal. "Pd-catalyzed Auto-Tandem Cascades Based on N-Sulfonylhydrazones: Hetero- and Carbocyclization Processes." Synthesis 28, no. 19 (August 10, 2017): 4434–47. http://dx.doi.org/10.1055/s-0036-1588535.

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The Pd-catalyzed cross-coupling between N-tosylhydrazones and organic halides is a powerful method for the creation of C–C bonds. This transformation has been included recently in cascade processes in which the same catalyst promotes various independent catalytic steps, a process known as auto-tandem catalysis. This strategy proves to be very useful for the construction of relatively complex carbo- and heterocyclic structures, as well as for the generation of molecular diversity. This short review will cover the different Pd-catalyzed auto-tandem reactions involving N-tosylhydrazones organized by the bond-forming sequence: C–C/C–N and C–C/C–C. Some examples of related tandem reactions leading to acyclic compounds are also highlighted.1 Introduction2 Auto-Tandem C–C/C–N Bond-Forming Reactions3 Auto-Tandem C–C/C–C Bond-Forming Reactions4 Tandem Reactions for the Synthesis of Linear Molecules5 Summary and Outlook

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10

Morita, Iori, Takahiro Mori, Takaaki Mitsuhashi, Shotaro Hoshino, Yoshimasa Taniguchi, Takashi Kikuchi, Kei Nagae, et al. "Exploiting a C–N Bond Forming Cytochrome P450 Monooxygenase for C–S Bond Formation." Angewandte Chemie 132, no. 10 (January 23, 2020): 4017–22. http://dx.doi.org/10.1002/ange.201916269.

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11

Morita, Iori, Takahiro Mori, Takaaki Mitsuhashi, Shotaro Hoshino, Yoshimasa Taniguchi, Takashi Kikuchi, Kei Nagae, et al. "Exploiting a C–N Bond Forming Cytochrome P450 Monooxygenase for C–S Bond Formation." Angewandte Chemie International Edition 59, no. 10 (January 23, 2020): 3988–93. http://dx.doi.org/10.1002/anie.201916269.

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12

Ameram, Nadiah, Farook Adam, Nur Nadia Fatihah, and Salih Al-Juaid. "Crystal structure of 2-methyl-N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 30, 2015): o356. http://dx.doi.org/10.1107/s2056989015007860.

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In the title compound, C15H15N3OS, there is an intramolecular N—H...O hydrogen bond and an intramolecular C—H...S hydrogen bond involving the C=O and C=S bonds which lie on opposite sides of the molecule. The molecule is non-planar with the benzene and pyridine rings being inclined to one another by 26.86 (9)°. In the crystal, molecules are linked by pairs of N—H...S hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The dimers are linkedviaC—H...S hydrogen bonds, forming slabs parallel to thebcplane.

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13

Bariwal, Jitender, and Erik Van der Eycken. "C–N bond forming cross-coupling reactions: an overview." Chemical Society Reviews 42, no. 24 (2013): 9283. http://dx.doi.org/10.1039/c3cs60228a.

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14

Rivera, Augusto, Juan Manuel Uribe, Jaime Ríos-Motta, Hector Jairo Osorio, and Michael Bolte. "Evidence for stereoelectronic effects in the N—C—N group of 8,10,12-triaza-1-azoniatetracyclo[8.3.1.18,12.02,7]pentadecane 4-nitrophenolate 4-nitrophenol monosolvate from the protonation of aminal (2R,7R)-1,8,10,12-tetraazatetracyclo[8.3.1.18,12.02,7]pentadecane: X-ray and natural bond orbital analysis." Acta Crystallographica Section C Structural Chemistry 71, no. 4 (March 14, 2015): 284–88. http://dx.doi.org/10.1107/s2053229615004829.

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The title molecular salt, C11H21N4+·C6H4NO3−·C6H5NO3, (II), crystallizes with two independent three-component aggregates in the asymmetric unit. In the cations, the cyclohexane rings fused to the cage azaadamantane systems both adopt a chair conformation. In the crystal structure, the aggregates are connected by C—H...O hydrogen bonds, forming a supramolecular unit enclosing anR44(24) ring motif. These units are linkedviaC—H...O and C—H...N hydrogen bonds, forming a three-dimensional network. Even hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction. The C—N bond distances provide structural evidence for a strong anomeric effect. The structure also displays O—H...O and N—H...O hydrogen bonding. Geometric optimization and natural bond orbital (NBO) analysis of (II) were undertaken by utilizing DFT/B3LYP with the 6-31+G(d,p) basis set. NBO second-order perturbation theory calculations indicate donor–acceptor interactions between nitrogen lone pairs and the antibonding orbital of the C—C and C—N bonds for the protonated polyamine, in agreement with the occurrence of bond-length and bond-angle changes within the aminal cage structure.

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15

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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16

Subasri, S., Ajay Kumar Timiri, Nayan Sinha Barji, Venkatesan Jayaprakash, Viswanathan Vijayan, and Devadasan Velmurugan. "Crystal structures of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(3-nitrophenyl)acetamide monohydrate andN-(2-chlorophenyl)-2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamide." Acta Crystallographica Section E Crystallographic Communications 72, no. 8 (July 22, 2016): 1171–75. http://dx.doi.org/10.1107/s2056989016011658.

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The title compounds, C12H12N6O3S·H2O, (I), and C12H12ClN5OS, (II), are 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamides. Compound (I) crystallized as a monohydrate. In both compounds, the molecules have a folded conformation, with the pyrimidine ring being inclined to the benzene ring by 56.18 (6)° in (I) and by 67.84 (6)° in (II). In both molecules, there is an intramolecular N—H...N hydrogen bond stabilizing the folded conformation. In (I), there is also a C—H...O intramolecular short contact, and in (II) an intramolecular N—H...Cl hydrogen bond is present. In the crystal of (I), molecules are linked by a series of N—H...O, O—H...O and O—H...N hydrogen bonds, forming undulating sheets parallel to the (100). The sheets are linkedviaan N—H...Owaterhydrogen bond, forming a three-dimensional network. In the crystal of (II), molecules are linked by a series of N—H...O, N—H...N and C—H...O hydrogen bonds, forming slabs parallel to (001).

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17

Boyarskaya, Dina, Margarita Avdontceva, and Tatiana Chulkova. "Synthesis and crystal structure of 2-isocyano-4-methylphenyl diphenylacetate: a rare case of an easily accessible odourless isocyanide." Acta Crystallographica Section C Structural Chemistry 71, no. 2 (January 31, 2015): 155–58. http://dx.doi.org/10.1107/s2053229615001588.

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Acidic hydrogen containing 2-isocyano-4-methylphenyl diphenylacetate, C22H17NO2, (I), was synthesized by the base-promoted reaction between 5-methylbenzoxazole and diphenylacetyl chloride. Achiral (I) crystallizes in the chiralP212121space group. The C[triple-bond]N bond length is 1.164 (2) Å and the angle between the OCO and 2-isocyano-4-methylphenyl planes is 69.10 (16)°. Molecules are linkedviaC=O...Hphenyland bifurcated N[triple-bond]C...Hphenyl/N[triple-bond]C...Hmethinehydrogen bonds, forming one-dimensional arrays.

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18

Begum, M. S., M. B. H. Howlader, M. C. Sheikh, R. Miyatake, and E. Zangrando. "Crystal structure ofS-hexyl (E)-3-(2-hydroxybenzylidene)dithiocarbazate." Acta Crystallographica Section E Crystallographic Communications 72, no. 3 (February 6, 2016): 290–92. http://dx.doi.org/10.1107/s2056989016001857.

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The title compound, C14H20N2OS2[systematic name:S-hexyl (E)-2-(2-hydroxybenzylidene)hydrazine-1-carbodithioate], crystallizes with four independent molecules (A–D) in the asymmetric unit. All four molecules adopt anEconformation with respect to the C=N bond of the benzylidene moiety and have an intramolecular O—H...N hydrogen bond generating anS(6) ring motif. In the crystal, theAandDmolecules are connected by a pair N—H...S hydrogen bonds, forming a dimer with anR22(8) ring motif. In the case of moleculesBandC, they are linked to themselves by pairs of N—H...S hydrogen bonds, formingB–BandC–Cinversion dimers withR22(8) ring motifs.

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19

Li, Zhengyi, Song Shi, Kun Zhou, Liang Chen, and Xiaoqiang Sun. "Crystal structure of (E)-2-({[2-(1,3-dioxan-2-yl)phenyl]imino}methyl)phenol." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 30, 2015): o357—o358. http://dx.doi.org/10.1107/s2056989015008051.

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The title compound, C17H17NO3, prepared by the condensation reaction of 2-(1,3-dioxan-2-yl)aniline and salicylaldehyde, has anEconformation about the C=N bond. The six-membered O-heterocycle adopts a chair conformation, with the bond to the aromatic ring located at its equatorial position. The dihedral angle between the aromatic rings is 36.54 (9)°. There is an intramolecular N—H...O hydrogen bond forming anS(6) ring motif. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming chains along thea-axis direction. Within the chains, there are C—H...π interactions involving adjacent molecules.

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20

Yu, Jianzhong, Peizhi Zhang, Jun Wu, and Zhicai Shang. "Metal-free C–N bond-forming reaction: straightforward synthesis of anilines, through cleavage of aryl C–O bond and amide C–N bond." Tetrahedron Letters 54, no. 24 (June 2013): 3167–70. http://dx.doi.org/10.1016/j.tetlet.2013.04.028.

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21

More, Atul A., Sourav K. Santra, and Alex M. Szpilman. "Azido-Enolonium Species in C–C and C–N Bond-Forming Coupling Reactions." Organic Letters 22, no. 3 (January 9, 2020): 768–71. http://dx.doi.org/10.1021/acs.orglett.9b03824.

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22

Odom, Aaron L. "New C–N and C–C bond forming reactions catalyzed by titanium complexes." Dalton Trans., no. 2 (2005): 225–33. http://dx.doi.org/10.1039/b415701j.

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23

Pradeep, P. S., S. Naveen, M. N. Kumara, K. M. Mahadevan, and N. K. Lokanath. "Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (August 30, 2014): 153–56. http://dx.doi.org/10.1107/s1600536814019254.

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In the title compound, C14H17FN2O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N—C bond distance [1.349 (3) Å] is substantially shorter than the sum of the covalent radii (dcov: C—N = 1.47 Å and C=N = 1.27 Å), which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming sheets lying parallel to (10-1). These two-dimensional networks are linkedviaC—H...F hydrogen bonds and C—H...π interactions, forming a three-dimensional structure.

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24

Novina, J. Josephine, G. Vasuki, M. Suresh, and M. Syed Ali Padusha. "(E)-N′-(3,4-Dimethoxybenzylidene)nicotinohydrazide monohydrate." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (June 18, 2014): o793—o794. http://dx.doi.org/10.1107/s1600536814013798.

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In the title hydrated compound, C15H15N3O3·H2O, the nicotinohydrazide molecule adopts atransconformation with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.10 (14)°. In the crystal, the solvent water molecule acts as an acceptor, forming an N—H...O hydrogen bond supported by two C—H...O contacts. It also acts as a donor, forming bifurcated O—H...(O,O) and O—H...N hydrogen bonds that combine with the former contacts to form zigzag chains of molecules along thec-axis direction. An additional O—H...O donor contact completes a set of six hydrogen bonds to and from the water molecule and connects it to a third nicotinohydrazide molecule. This latter contact combines with weaker C—H...O hydrogen bonds supported by a C—H...π contact to stack molecules alongbin a three-dimensional network.

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25

Strieth-Kalthoff, Felix, Ashley R. Longstreet, Jessica M. Weber, and Timothy F. Jamison. "Bench-Stable N -Heterocyclic Carbene Nickel Precatalysts for C−C and C−N Bond-Forming Reactions." ChemCatChem 10, no. 13 (May 2, 2018): 2873–77. http://dx.doi.org/10.1002/cctc.201800454.

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26

Moriguchi, Tetsuji, Venkataprasad Jalli, Suvratha Krishnamurthy, Akihiko Tsuge, and Kenji Yoza. "Crystal structure of ethyl 2-(2-{1-[N-(4-bromophenyl)-2-oxo-2-phenylacetamido]-2-tert-butylamino-2-oxoethyl}-1H-pyrrol-1-yl)acetate." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (December 1, 2015): o1049—o1050. http://dx.doi.org/10.1107/s2056989015023592.

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In the title compound, C28H30BrN3O5, there is an intramolecular N—H...O hydrogen bond and an intramolecular C—H...O hydrogen bond, both formingS(9) ring motifs. The planes of the 4-bromophenyl ring and the phenyl ring are inclined to that of the pyrrole ring by 48.05 (12) and 77.45 (14)°, respectively, and to one another by 56.25 (12)°. In the crystal, molecules are linkedviaC—H...O hydrogen bonds and C—H...π interactions, forming slabs parallel to (10-1).

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27

Flörke, Ulrich, and Birte Drewes. "(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyltetrahydrofuran-3,4-diol." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (October 16, 2013): o1646—o1647. http://dx.doi.org/10.1107/s1600536813027931.

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The molecular structure of the title compound, C11H13IN4O3, shows a ribofuranosyl–pyrrolo O—C—N—C torsion angle of 59.1 (3)°, with the central C—N bond length being 1.446 (3) Å. The C—I bond length is 2.072 (2) Å. The amino group is coplanar with the attached aromatic ring [C—N—C—N torsion angle = −178.8 (2)°] and forms an intramolecular N—H...I hydrogen bond. In the crystal, O—H...N and N—H...O hydrogen bonds link the molecules into puckered layers parallel to (001). These layers are bound to each other by secondary I...O interactions [3.2250 (17) Å], forming a three-dimensional framework.

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28

Nanda, Santosh Kumar, and Rosy Mallik. "1,2-Difunctionalizations of alkynes entailing concomitant C–C and C–N bond-forming carboamination reactions." RSC Advances 12, no. 10 (2022): 5847–70. http://dx.doi.org/10.1039/d1ra06633a.

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29

Nagasawa, Masayuki, Yuji Sasanuma, and Hyuma Masu. "N,N′-(Ethane-1,2-diyl)dibenzenecarbothioamide." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (April 18, 2014): o586. http://dx.doi.org/10.1107/s1600536814008368.

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The title compound, C16H16N2S2, adopts agauche+–gauche+–gauche+(g+g+g+) conformation in the NH—CH2—CH2—NH bond sequence. In the crystal, molecules are connected by pairs of N—H...S=C hydrogen bonds and C—H...π interactions, forming a tape structure along thec-axis direction.

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30

Rivera, Augusto, Jicli José Rojas, Jaime Ríos-Motta, and Michael Bolte. "Crystal structure of the co-crystalline adduct 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD)–4-chloro-3,5-dimethylphenol (1/1)." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (June 3, 2015): 737–40. http://dx.doi.org/10.1107/s2056989015010257.

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In the crystal of the title co-crystalline adduct, C8H16N4·C8H9ClO, (I), prepared by solid-state reaction, the molecules are linked by intermolecular O—H...N hydrogen bonds, forming aDmotif. The azaadamantane structure in (I) is slightly distorted, with N—CH2—CH2—N torsion angles of 10.4 (3) and −9.0 (3)°. These values differ slightly from the corresponding torsion angles in the free aminal cage (0.0°) and in related co-crystalline adducts, which are not far from a planar geometry and consistent with aD2dmolecular symmetry in the tetraazatricyclo structure. The structures also differ in that there is a slight elongation of the N—C bond lengths about the N atom that accepts the hydrogen bond in (I) compared with the other N—C bond lengths. In the crystal, the two molecules are not only linked by a classical O—H...N hydrogen bond but are further connected by weak C—H...π interactions, forming a two-dimensional supramolecular network parallel to thebcplane.

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Kargar, Hadi, Zahra Sharafi, Reza Kia, and Muhammad Nawaz Tahir. "(E)-3-[(3-Ethoxy-2-hydroxybenzylidene)amino]benzoic acid." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 10, 2012): o1035. http://dx.doi.org/10.1107/s1600536812009968.

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In the title compound, C16H15NO4, a potential bidentateN,O-donor Schiff base ligand, the benzene rings are inclined to one another by 4.24 (12)°. The molecule has anEconformation about the C=N bond. An intramolecular O—H...N hydrogen bond makes anS(6) ring motif. In the crystal, pairs of O—H...O hydrogen bonds link the molecules, forming inversion dimers withR22(8) ring motifs. These dimers are further connected by C—H...O interactions, forming a sheet in (104). There is also a C—H...π interaction present involving neighbouring molecules.

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32

Ghichi, Nadir, Mohamed Amine Benaouida, Ali Benboudiaf, and Hocine Merazig. "Crystal structure of (E)-5-benzyloxy-2-{[(4-nitrophenyl)imino]methyl}phenol." Acta Crystallographica Section E Crystallographic Communications 71, no. 12 (November 28, 2015): o1000—o1001. http://dx.doi.org/10.1107/s2056989015022173.

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In the title compound, C20H16N2O4, the molecule adopts anEconformation about the N=C bond. There is an intramolecular O—H...N hydrogen bond forming anS(6) ring motif. The nitrobenzene and benzyloxy rings are inclined to the central benzene ring by 4.34 (10) and 27.66 (11)°, respectively, and to one another by 31.40 (12)°. In the crystal, molecules are linkedviaC—H...O hydrogen bonds, forming zigzag chains along [001]. Within the chains there are C—H...π interactions present. The chains are linkedviaπ–π interactions [inter-centroid distance = 3.7048 (15) Å], forming slabs parallel to thebcplane.

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33

Zhong, Qi-Di, Sheng-Quan Hu, and Hong Yan. "Crystal structure of 1-benzyl-4-formyl-1H-pyrrole-3-carboxamide." Acta Crystallographica Section E Crystallographic Communications 72, no. 2 (January 9, 2016): 133–35. http://dx.doi.org/10.1107/s2056989016000128.

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In the title compound, C13H12N2O2(I), the mean planes of the pyrrole and benzyl rings are approximately perpendicular, forming a dihedral angle of 87.07 (4) °. There is an intramolecular N—H...O hydrogen bond forming an S(7) ring motif. In the crystal, molecules are linkedviaa pair of N—H...O hydrogen bonds forming inversion dimers. C—H...O hydrogen bonds link the dimers into chains along direction [10-1]. The chains are further linked by weak C—H...π interactions forming layers parallel to theacplane.

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34

Naziri, Mir Abolfazl, Ertan Şahin, and Tuncer Hökelek. "Crystal structure and Hirshfeld surface analysis of (E)-4-{[2-(4-hydroxybenzoyl)hydrazin-1-ylidene]methyl}pyridin-1-ium nitrate." Acta Crystallographica Section E Crystallographic Communications 74, no. 3 (February 7, 2018): 323–27. http://dx.doi.org/10.1107/s2056989018002141.

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The asymmetric unit of the title aroyl hydrazone Schiff base salt, C13H12N3O2+·N O3−, consists of one molecular cation in the keto tautomeric form, adopting anEconfiguration with respect to the azomethine bond, and one nitrate anion. The two units are linkedviaan N—H...O hydrogen bond. The molecule overall is non-planar, with the pyridinium and benzene rings being inclined to each other by 4.21 (4)°. In the crystal, cations and anions are linkedviaintermolecular O—H...O and bifurcated N—H...O hydrogen bonds, forming a two-dimensional network parallel to (101). These networks are further linked by C—H...O hydrogen bonds, forming slabs parallel to (101). The slabs are linked by offset π–π interactions, involving the benzene and pyridinium rings of adjacent slabs [intercentroid distance = 3.610 (2) Å], forming a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...O/O...H (45.1%), H...H (19.3%), H...C/C...H (14.5%), H...N/N...H (7.9%) and C...C (6.0%) interactions.

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35

Buchspies, Jonathan, Md Mahbubur Rahman, and Michal Szostak. "Transamidation of Amides and Amidation of Esters by Selective N–C(O)/O–C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)–NHC Complexes." Molecules 26, no. 1 (January 2, 2021): 188. http://dx.doi.org/10.3390/molecules26010188.

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The formation of amide bonds represents one of the most fundamental processes in organic synthesis. Transition-metal-catalyzed activation of acyclic twisted amides has emerged as an increasingly powerful platform in synthesis. Herein, we report the transamidation of N-activated twisted amides by selective N–C(O) cleavage mediated by air- and moisture-stable half-sandwich Ni(II)–NHC (NHC = N-heterocyclic carbenes) complexes. We demonstrate that the readily available cyclopentadienyl complex, [CpNi(IPr)Cl] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), promotes highly selective transamidation of the N–C(O) bond in twisted N-Boc amides with non-nucleophilic anilines. The reaction provides access to secondary anilides via the non-conventional amide bond-forming pathway. Furthermore, the amidation of activated phenolic and unactivated methyl esters mediated by [CpNi(IPr)Cl] is reported. This study sets the stage for the broad utilization of well-defined, air- and moisture-stable Ni(II)–NHC complexes in catalytic amide bond-forming protocols by unconventional C(acyl)–N and C(acyl)–O bond cleavage reactions.

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36

Ghichi, Nadir, Chawki Bensouici, Ali Benboudiaf, Yacine DJebli, and Hocine Merazig. "Crystal structures and antioxidant capacity of (E)-5-benzyloxy-2-{[(4-chlorophenyl)imino]methyl}phenol and (E)-5-benzyloxy-2-({[2-(1H-indol-3-yl)ethyl]iminiumyl}methyl)phenolate." Acta Crystallographica Section E Crystallographic Communications 74, no. 4 (March 9, 2018): 478–82. http://dx.doi.org/10.1107/s2056989018003687.

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The title Schiff base compounds, C20H16ClNO2(I) and C24H22N2O2(II), were synthesizedviathe condensation reaction of 2-amino-4-chlorophenol for (I), and 2-(2,3-dihydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benzyloxy-2-hydroxybenzaldehyde. In both compounds, the configuration about the C=N imine bond isE. Neither molecule is planar. In (I), the central benzene ring makes dihedral angles of 49.91 (12) and 53.52 (11)° with the outer phenyl and chlorophenyl rings, respectively. In (II), the central benzene ring makes dihedral angles of 89.59 (9) and 72.27 (7)°, respectively, with the outer phenyl ring and the mean plane of the indole ring system (r.m.s. deviation = 0.011 Å). In both compounds there is an intramolecular hydrogen bond forming anS(6) ring motif; an O—H...O hydrogen bond in (I), but a charge-assisted N+—H...O−hydrogen bond in (II). In the crystal of (I), molecules are linked by C—H...π interactions, forming slabs parallel to plane (001). In the crystal of (II), molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers. The dimers are linked by C—H...O hydrogen bonds, C—H...π interactions and a weak N—H...π interaction, forming columns propagating along thea-axis direction. The antioxidant capacity of the synthesized compounds was determined by cupric reducing antioxidant capacity (CUPRAC) for compound (I) and by 2,2-picrylhydrazyl hydrate (DPPH) for compound (II).

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37

Özek, Arzu, Çiğdem Albayrak, Mustafa Odabaşoğlu, and Orhan Büyükgüngör. "(E)-1-[4-(2,4-Dihydroxybenzylideneamino)phenyl]ethanone sesquihydrate." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 31, 2007): o4457. http://dx.doi.org/10.1107/s1600536807052373.

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The asymmetric unit of the title compound, C15H13NO3·1.5H2O, consists of one ethanone molecule, one water molecule and one half-molecule of water. The organic molecule is a phenol–imine tautomer, as evidenced from C—O, C—N and C—C bond lengths and it is stabilized by an intramolecular O—H...N hydrogen bond which generates an S(6) ring motif. It is nearly planar, with a dihedral angle of 1.40 (10)° between the two aromatic rings. Molecules are linked by three intermolecular O—H...O hydrogen bonds, forming dimers, and are further linked by C—H...π interactions, forming a three-dimensional network.

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38

Eisenberger, Patrick, and Laurel L. Schafer. "Catalytic synthesis of amines and N-containing heterocycles: Amidate complexes for selective C–N and C–C bond-forming reactions." Pure and Applied Chemistry 82, no. 7 (May 31, 2010): 1503–15. http://dx.doi.org/10.1351/pac-con-09-11-27.

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The direct, 100 % atom-economic, and selective synthesis of amines is a challenging task that can be achieved, making use of early transition-metal catalysts. Here we report the synthesis and application of group 4 and 5 high-oxidation-state metal amidate complexes in catalytic C–N (hydroamination) and C–C (hydroaminoalkylation) bond-forming reactions to access substituted amines.

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39

Mohamed, Shaaban K., Mehmet Akkurt, Antar A. Abd Elhamid, Kuldip Singh, and Herman Potgieter. "(6Z)-4-Bromo-6-{[(2-hydroxyethyl)amino]methylidene}cyclohexa-2,4-dien-1-one." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (March 10, 2012): o1020. http://dx.doi.org/10.1107/s1600536812009749.

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The title molecule, C9H10BrNO2, excluding methylene H atoms and the C—OH group, is essentially planar, with a maximum deviation of 0.037 (2) Å for the N atom. The N—C—C—O torsion angle is −63.1 (3)°. The molecular structure is stabilized by a weak intramolecular N—H...O(carbonyl) hydrogen bond, forming anS(6) motif. In the crystal, molecules are linked by O—H...O and C—H...O hydrogen bonds, forming a three-dimensional network.

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40

Sravya, S., S. Sruthy, N. Aiswarya, M. Sithambaresan, and M. R. Prathapachandra Kurup. "Crystal structure of (E)-N′-(5-bromo-2-hydroxybenzylidene)nicotinohydrazide monohydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (June 3, 2015): 734–36. http://dx.doi.org/10.1107/s2056989015009627.

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In the title compound, C13H10BrN3O2·H2O, the conformation about the azomethine double bond isE. The molecule exists in the amido form with a C=O bond length of 1.229 (2) Å. There is an intramolecular O—H...N hydrogen bond forming anS(6) ring motif. The whole molecule is almost planar, with an r.m.s. deviation of 0.021 Å for all non-H atoms, and the dihedral angle between the planes of the pyridine and benzene rings is 0.74 (12)°. In the crystal, the water molecule of crystallization links the organic moleculesviaOw—H...O, Ow—H...N and N—H...Ow hydrogen bonds and short C—H...Ow contacts, forming sheets lying parallel to (100). Within the sheets there is a weak π–π interaction involving the pyridine and benzene rings [centroid-to-centroid distance = 3.8473 (15) Å]. The sheets are linkedviaC—H...Br interactions, forming a three-dimensional network.

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41

Karthikeyan, S., K. Sethusankar, Anthonisamy Devaraj, and Manickam Bakthadoss. "Methyl 4′-(3-bromophenyl)-3′-(2,5-dimethylbenzyl)-1′-methyl-2-oxospiro[indoline-3,2′-pyrrolidine]-3′-carboxylate." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (February 15, 2014): o299—o300. http://dx.doi.org/10.1107/s1600536814002967.

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In the title compound, C29H29BrN2O3, the indole ring system is essentially planar (r.m.s. deviation = 0.079 Å) and makes a dihedral angle of 85.23 (10)° with the mean plane of the 4-methylpyrrolidine ring. This ring adopts an envelope conformation with the N atom at the flap. The pyrrolidine ring of the indole ring system adopts a twisted conformation on the C—C(=O) bond. The molecular structure is stabilized by an intramolecular C—H...O hydrogen bond, which generates anS(6) ring motif. In the crystal, molecules are linkedviapairs of C—H...O hydrogen bonds, forming inversion dimers with anR22(14) ring motif. These dimers are further linked by N—H...O and C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to (10-1).

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42

Choudhury, Manisha, Vijayan Viswanathan, Ajay Kumar Timiri, Barij Nayan Sinha, Venkatesan Jayaprakash, and Devadasan Velmurugan. "Crystal structures and Hirshfeld surface analyses of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide." Acta Crystallographica Section E Crystallographic Communications 74, no. 5 (April 27, 2018): 718–23. http://dx.doi.org/10.1107/s2056989018005704.

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In the title compounds, C11H12N6OS (I) and C10H11N7OS (II), the diaminopyrimidine ring makes dihedral angles of 71.10 (9)° with the pyridine ring in (I) and 62.93 (15)° with the pyrazine ring in (II). The ethanamine group, –CH2–C(=O)–NH– lies in the plane of the pyridine and pyrazine rings in compounds (I) and (II), respectively. In both compounds, there is an intramolecular N—H...N hydrogen bond forming anS(7) ring motif and a short C—H...O interaction forming anS(6) loop. In the crystals of both compounds, molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers withR22(8) ring motifs. In (I), the dimers are linked by N—H...O and N—H...N hydrogen bonds, forming layers parallel to (1\overline{1}\overline{1}). The layers are linked by offset π–π interactions [intercentroid distance = 3.777 (1) Å], forming a three-dimensional supramolecular structure. In (II), the dimers are linked by N—H...O, N—H...N and C—H...O hydrogen bonds, also forming a three-dimensional supramolecular structure.

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43

Subasri, S., Timiri Ajay Kumar, Barij Nayan Sinha, Venkatesan Jayaprakash, Vijayan Viswanathan, and Devadasan Velmurugan. "Crystal structures of 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(naphthalen-1-yl)acetamide and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(4-fluorophenyl)acetamide." Acta Crystallographica Section E Crystallographic Communications 73, no. 2 (January 31, 2017): 306–9. http://dx.doi.org/10.1107/s2056989017001293.

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The title compounds, C16H15N5OS, (I), and C12H12FN5OS, (II), are [(diaminopyrimidine)sulfanyl]acetamide derivatives. In (I), the pyrimidine ring is inclined to the naphthalene ring system by 55.5 (1)°, while in (II), the pyrimidine ring is inclined to the benzene ring by 58.93 (8)°. In (II), there is an intramolecular N—H...N hydrogen bond and a short C—H...O contact. In the crystals of (I) and (II), molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers withR22(8) ring motifs. In the crystal of (I), the dimers are linked by bifurcated N—H...(O,O) and C—H...O hydrogen bonds, forming layers parallel to (100). In the crystal of (II), the dimers are linked by N—H...O hydrogen bonds, also forming layers parallel to (100). The layers are linked by C—H...F hydrogen bonds, forming a three-dimensional architecture.

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44

Correa, Arkaitz, and Marcos Segundo. "Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides." Synthesis 50, no. 15 (June 25, 2018): 2853–66. http://dx.doi.org/10.1055/s-0037-1610073.

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The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

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45

Nagasawa, Masayuki, Yuji Sasanuma, and Hyuma Masu. "N,N′-(Propane-1,3-diyl)dibenzothioamide." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (May 3, 2014): o639. http://dx.doi.org/10.1107/s160053681400974x.

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The title compound, C17H18N2S2, exhibits atrans–trans–trans–gauche+(tttg+) conformation with regard to the NH–CH2–CH2–CH2–NH bond sequence. In the crystal, molecules are connected by N—H...S=C and C—H...S=C hydrogen bonds, forming a herringbone arrangement along thec-axis direction. The two thioamide groups make dihedral angles of 43.0 (2) and 33.1 (2)° with the adjacent phenyl rings.

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46

Purandara, H., Sabine Foro, and B. Thimme Gowda. "Crystal structure of (E)-4-methyl-N-{2-[2-(4-nitrobenzylidene)hydrazin-1-yl]-2-oxoethyl}benzenesulfonamideN,N-dimethylformamide monosolvate." Acta Crystallographica Section E Crystallographic Communications 73, no. 11 (October 20, 2017): 1683–86. http://dx.doi.org/10.1107/s2056989017014669.

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The molecule of the title Schiff base compound, C16H16N4O5S·C3H7NO, displays atransconformation with respect to the C=N double bond. The C—N and N—N bonds are relatively short compared to their normal bond lengths, indicating some degree of delocalization in the molecule. The molecule is bent at the S atom, with an S—N—C—C torsion angle of 164.48 (11)°. The dihedral angle between the two aromatic rings is 84.594 (7)°. Intermolecular N—H...O and C —H...O hydrogen bonds connect centrosymmetrically related molecules into dimers forming rings ofR33(11) andR22(10) graph-set motif stacked along theaaxis into a columnar arrangement. The molecular columns are further linked into a three-dimensional network by C—H...π interactions.

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47

Meany, Joseph E., Steven P. Kelley, Robin D. Rogers, and Stephen A. Woski. "Crystal structure of 4′-bromo-2,5-dihydroxy-2′,5′-dimethoxy-[1,1′-biphenyl]-3,4-dicarbonitrile." Acta Crystallographica Section E Crystallographic Communications 72, no. 5 (April 12, 2016): 667–70. http://dx.doi.org/10.1107/s2056989016005715.

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In the crystal of the title substituted hemibiquinone derivative, C16H11BrN2O4or [BrHBQH2(CN)2], the substituted benzene rings are rotated about the central C—C bond, forming a dihedral angle of 53.59 (7)°. The ring systems interact through an intramolecular O—H...Omethoxyhydrogen bond, which induces a geometry quite different from those in previously reported hemibiquinone structures. In the crystal, the molecules associate through an intermolecular O—H...Nnitrilehydrogen bond, forming chains which extend along [100] and are interlinked through very weak C—H...N hydrogen bonds, giving a overall two-dimensional structure lying parallel to (010).

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48

Yu, Jianzhong, Peizhi Zhang, Jun Wu, and Zhicai Shang. "ChemInform Abstract: Metal-Free C-N Bond-Forming Reaction: Straightforward Synthesis of Anilines, Through Cleavage of Aryl C-O Bond and Amide C-N Bond." ChemInform 44, no. 39 (September 5, 2013): no. http://dx.doi.org/10.1002/chin.201339062.

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49

Kargar, Hadi, Reza Kia, and Muhammad Nawaz Tahir. "(E)-4-Amino-N′-(2-hydroxy-5-methoxybenzylidene)benzohydrazide monohydrate." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (July 4, 2012): o2321—o2322. http://dx.doi.org/10.1107/s1600536812026633.

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In the title compound, C15H15N3O3·H2O, the hydazide Schiff base molecule shows anEconformation around the C=N bond. An intramolecular O—H...N hydrogen bond makes anS(6) ring motif. The dihedral angle between the substituted phenyl rings is 23.40 (11)°. The water molecule mediates linking of neighbouring molecules through O—H...(O,O) hydrogen bonds into infinite chains along theaaxis, which are further connected together through N—H...O hydrogen bonds, forming a two-dimensional network parallel to (001). C—H...O interactions aso occur.

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50

Madasu, Jayashree, Shital Shinde, Rudradip Das, Sagarkumar Patel, and Amit Shard. "Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions." Organic & Biomolecular Chemistry 18, no. 41 (2020): 8346–65. http://dx.doi.org/10.1039/d0ob01382j.

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