Journal articles: 'Bond forming'

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Dyball, H. "Forming a bond." Electronics Letters 46, no. 14 (2010): 962. http://dx.doi.org/10.1049/el.2010.9086.

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Day, Lin. "Forming a loving bond." Early Years Educator 10, no. 2 (June 2008): 32–34. http://dx.doi.org/10.12968/eyed.2008.10.2.29168.

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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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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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Green, Nicholas J., and Michael S. Sherburn. "Multi-Bond Forming Processes in Efficient Synthesis." Australian Journal of Chemistry 66, no. 3 (2013): 267. http://dx.doi.org/10.1071/ch13003.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Gagné, Olivier Charles, Patrick H. J. Mercier, and Frank Christopher Hawthorne. "A priori bond-valence and bond-length calculations in rock-forming minerals." Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials 74, no. 6 (December 1, 2018): 470–82. http://dx.doi.org/10.1107/s2052520618010442.

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Within the framework of the bond-valence model, one may write equations describing the valence-sum rule and the loop rule in terms of the constituent bond valences. These are collectively called the network equations, and can be solved for a specific bond topology to calculate its a priori bond valences. A priori bond valences are the ideal values of bond strengths intrinsic to a given bond topology that depend strictly on the formal valences of the ion at each site in the structure, and the bond-topological characteristics of the structure (i.e. the ion connectivity). The a priori bond valences are calculated for selected rock-forming minerals, beginning with a simple example (magnesiochromite, = 1.379 bits per atom) and progressing through a series of gradually more complex minerals (grossular, diopside, forsterite, fluoro-phlogopite, phlogopite, fluoro-tremolite, tremolite, albite) to finish with epidote (= 4.187 bits per atom). The effects of weak bonds (hydrogen bonds, long Na+—O2− bonds) on the calculation of a priori bond valences and bond lengths are examined. For the selected set of minerals, a priori and observed bond valences and bond lengths scatter closely about the 1:1 line with an average deviation of 0.04 v.u. and 0.048 Å and maximum deviations of 0.16 v.u. and 0.620 Å. The scatter of the corresponding a priori and observed bond lengths is strongly a function of the Lewis acidity of the constituent cation. For cations of high Lewis acidity, the range of differences between the a priori and observed bond lengths is small, whereas for cations of low Lewis acidity, the range of differences between the a priori and observed bond lengths is large. These calculations allow assessment of the strain in a crystal structure and provide a way to examine the effect of bond topology on variation in observed bond lengths for the same ion-pair in different bond topologies.

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Reardon-Robinson, Melissa E., and Hung Ton-That. "Disulfide-Bond-Forming Pathways in Gram-Positive Bacteria." Journal of Bacteriology 198, no. 5 (December 7, 2015): 746–54. http://dx.doi.org/10.1128/jb.00769-15.

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Disulfide bonds are important for the stability and function of many secreted proteins. In Gram-negative bacteria, these linkages are catalyzed by thiol-disulfide oxidoreductases (Dsb) in the periplasm. Protein oxidation has been well studied in these organisms, but it has not fully been explored in Gram-positive bacteria, which lack traditional periplasmic compartments. Recent bioinformatics analyses have suggested that the high-GC-content bacteria (i.e., actinobacteria) rely on disulfide-bond-forming pathways. In support of this, Dsb-like proteins have been identified inMycobacterium tuberculosis, but their functions are not known.Actinomyces orisandCorynebacterium diphtheriaehave recently emerged as models to study disulfide bond formation in actinobacteria. In both organisms, disulfide bonds are catalyzed by the membrane-bound oxidoreductase MdbA. Remarkably, unlike known Dsb proteins, MdbA is important for pathogenesis and growth, which makes it a potential target for new antibacterial drugs. This review will discuss disulfide-bond-forming pathways in bacteria, with a special focus on Gram-positive bacteria.

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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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Curtis, Richard, R. Omar, J. Bahra, M. Ditta, A. Chotai, and Lucy DiSilvio. "Superplastic Prosthetic Forming - In Vitro Response." Key Engineering Materials 433 (March 2010): 31–39. http://dx.doi.org/10.4028/www.scientific.net/kem.433.31.

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Steinemann, 1998 [1] reported an observation made several decades earlier in 1951, by Leventhal [2] in which ‘bone reaction was studied by the insertion of up to 80 titanium screws into the femora of rats. At the end of sixteen weeks the screws were so tight that in one specimen the femur was fractured when an attempt was made to remove the screw’. Consequently, the main reasons given for the suitability of titanium for surgical implantation are its strength, its failure to cause tissue reaction, and the fact that bone becomes attached to titanium. Now, we call this attachment osseointegration which is considered to be the direct structural and functional connection between living bone and the surface of a load-bearing artificial implant. However, osseointegration is not considered to be a chemical bond between titanium and bone. Implant materials that actually bond to bone are considered to be bioactive. Materials for clinical use can be classified into three categories: resorbable, bioactive and nearly inert materials. A bioactive material is defined as a material that elicits a specific biological response at the interface of the material, which results in the formation of a bond between the tissue and that material. Whereas specific bioceramics are considered to be bioactive, titanium alloys are not normally considered to be so. However, recent surface modification of titanium alloys provide evidence that titanium alloys can become bioactive after treatment with NaOH and the ensuing development of a titanate gel on the metal surface.

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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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11

Terao, Jun, Hirohisa Todo, Hiroyasu Watabe, Aki Ikumi, Yoshiaki Shinohara, and Nobuaki Kambe. "Carbon-carbon bond-forming reactions using alkyl fluorides." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 941–51. http://dx.doi.org/10.1351/pac200880050941.

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This account reviews C-C bond formation reactions using alkyl fluorides mostly focusing on the transition-metal-catalyzed reactions. These reactions proceed efficiently under mild conditions by the combined use of Grignard reagents and transition-metal catalysts, such as Ni, Cu, and Zr. It is proposed that ate complex intermediates formed by the reaction of these transition metals with Grignard reagents play important roles as the active catalytic species. Organoaluminun reagents react directly with alkyl fluorides in nonpolar solvents at room temperature to form C-C bonds. These studies demonstrate the practical usefulness of alkyl fluorides in C-C bond formation reactions and provide a promising method for the construction of carbon frameworks employing alkyl fluorides. The scope and limitations, as well as reaction pathways, are discussed.

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12

Waterman, Rory. "Dehydrogenative Bond-Forming Catalysis Involving Phosphines." Current Organic Chemistry 12, no. 15 (October 1, 2008): 1322–39. http://dx.doi.org/10.2174/138527208785909592.

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13

Chauhan, Pankaj, Suruchi Mahajan, and Dieter Enders. "Organocatalytic Carbon–Sulfur Bond-Forming Reactions." Chemical Reviews 114, no. 18 (August 21, 2014): 8807–64. http://dx.doi.org/10.1021/cr500235v.

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14

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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15

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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Vusak, Vitomir, Darko Vusak, Kresimir Molcanov, and Mestrovic Ernest. "Synthesis, crystal structure and spectroscopic and Hirshfeld surface analysis of 4-hydroxy-3-methoxy-5-nitrobenzaldehyde." Acta Crystallographica Section E Crystallographic Communications 76, no. 2 (January 21, 2020): 239–44. http://dx.doi.org/10.1107/s2056989020000225.

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The title compound, C8H7NO5, is planar with an r.m.s. deviation for all non-hydrogen atoms of 0.018 Å. An intramolecular O—H...O hydrogen bond involving the adjacent hydroxy and nitro groups forms an S(6) ring motif. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by C—H...O hydrogen bonds, forming layers parallel to the bc plane. The layers are linked by a further C—H...O hydrogen bond, forming slabs, which are linked by C=O...π interactions, forming a three-dimensional supramolecular structure. Hirshfeld surface analysis was used to investigate intermolecular interactions in the solid state. The molecule was also characterized spectroscopically and its thermal stability investigated by differential scanning calorimetry and by thermogravimetric analysis.

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17

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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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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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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20

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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21

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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Yartsev, Yegor, Vitaliy Palchikov, Alexandr Gaponov, and Svitlana Shishkina. "Crystal structure of 5-chloro-N1-(5-phenyl-1H-pyrazol-3-yl)benzene-1,2-diamine." Acta Crystallographica Section E Crystallographic Communications 73, no. 6 (May 26, 2017): 876–79. http://dx.doi.org/10.1107/s2056989017007381.

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The title compound, C15H13ClN4, crystallizes with two independent molecules (AandB) in the asymmetric unit, which are far from planar as a result of steric repulsion between the rings. The benzene and phenyl rings are inclined to the central pyrazole ring by 46.64 (10) and 17.87 (10)° in moleculeA, and by 40.02 (10) and 14.18 (10)° in moleculeB. The aromatic rings are inclined to one another by 58.77 (9)° in moleculeA, and 36.95 (8)° in moleculeB. In the crystal, theAandBmolecules are linked by two pairs of N—H...N hydrogen bonds formingA–Bdimers. These are further linked by a fifth N—H...N hydrogen bond, forming tetramer-like units that stack along thea-axis direction, forming columns, which are in turn linked by C—H...π interactions, forming layers parallel to theacplane.

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23

Bracchi, Michael E., and David A. Fulton. "Orthogonal breaking and forming of dynamic covalent imine and disulfide bonds in aqueous solution." Chemical Communications 51, no. 55 (2015): 11052–55. http://dx.doi.org/10.1039/c5cc02716k.

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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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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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Savithri, M. P., P. S. Yuvaraj, B. S. R. Reddy, R. Raja, and A. SubbiahPandi. "Crystal structure of methyl (E)-2-(1-methyl-2-oxoindolin-3-ylidene)acetate." Acta Crystallographica Section E Crystallographic Communications 71, no. 3 (February 21, 2015): o188—o189. http://dx.doi.org/10.1107/s2056989015003217.

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The title compound, C12H11NO3, is essentially planar, with the mean plane of the acetate side chain [–C—C(=O)—O—C] being inclined to the mean plane of the indole ring system by 12.49 (7)°. The five- and six-membered rings of the indole group are almost coplanar, making a dihedral angle of 1.76 (8)°. The conformation about the C=C bond isEand there is an intramolecular C—H...O hydrogen bond present. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds forming inversion dimers, with anR22(16) ring motif. The dimers are linked by a second pair of C—H...O hydrogen bonds, enclosingR22(16) ring motifs, forming ribbons lying parallel to (-114). The ribbons are linkedviaC—H...π interactions, forming a three-dimensional structure.

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27

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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Faizi, Md Serajul Haque, Necmi Dege, Ashanul Haque, Valentina A. Kalibabchuk, and Mustafa Cemberci. "Crystal structure of (E)-2,6-di-tert-butyl-4-{[2-(2,4-dinitrophenyl)hydrazinylidene]methyl}phenol." Acta Crystallographica Section E Crystallographic Communications 73, no. 2 (January 6, 2017): 96–98. http://dx.doi.org/10.1107/s2056989016020107.

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The essential part (including all the non-hydrogen atoms except two methyl carbons) of the molecule of the title compound, C21H26N4O5, lies on a mirror plane, which bisects thet-butyl groups. The conformation of the C=N bond of this Schiff base compound isE, and there is an intramolecular N—H...O hydrogen bond present, forming anS(6) ring motif. In the crystal, molecules are linkedviaO—H...O hydrogen bonds, forming zigzag chains propagating along thea-axis direction. There are no other significant intermolecular contacts present.

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29

Evano, Gwilherm, Jianjun Wang, and Antoine Nitelet. "Metal-mediated C–O bond forming reactions in natural product synthesis." Organic Chemistry Frontiers 4, no. 12 (2017): 2480–99. http://dx.doi.org/10.1039/c7qo00671c.

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Metal catalyzed reactions for the formation of C(sp²)–O bonds have had a dramatic impact in natural product synthesis. They have enabled the emergence of new bond disconnections, which notably resulted in remarkably efficient and short synthetic pathways. The use of these reactions for the formation of C–O bonds in natural product synthesis is overviewed in this critical review.

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30

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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KANAMORI, Satoshi, Nami OHASHI, Hiroaki ISHIDA, Keiko YAMAMOTO, and Toshimasa ITOH. "HNF4α Is a Covalent Bond-Forming Receptor." Journal of Nutritional Science and Vitaminology 67, no. 2 (April 30, 2021): 126–29. http://dx.doi.org/10.3177/jnsv.67.126.

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32

Landeta, Cristina, Laura McPartland, Ngoc Q. Tran, Brian M. Meehan, Yifan Zhang, Zaidi Tanweer, Shoko Wakabayashi, et al. "Inhibition ofPseudomonas aeruginosaandMycobacterium tuberculosisdisulfide bond forming enzymes." Molecular Microbiology 111, no. 4 (March 18, 2019): 918–37. http://dx.doi.org/10.1111/mmi.14185.

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33

Reggelin, M., S. Slavik, and P. Bühle. "C−C Bond-Forming Desulfurizations of Sulfoximines." Organic Letters 10, no. 18 (September 18, 2008): 4081–84. http://dx.doi.org/10.1021/ol8015995.

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34

Corma, A., A. Leyva-Pérez, and Maria J. Sabater. "Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions." Chemical Reviews 111, no. 3 (March 9, 2011): 1657–712. http://dx.doi.org/10.1021/cr100414u.

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35

Lorsbach, Beth A., and Mark J. Kurth. "Carbon−Carbon Bond Forming Solid-Phase Reactions." Chemical Reviews 99, no. 6 (June 1999): 1549–82. http://dx.doi.org/10.1021/cr970109y.

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36

Petit, C., and J. L. Montchamp. "ChemInform Abstract: C-P Bond-Forming Reactions." ChemInform 44, no. 35 (August 8, 2013): no. http://dx.doi.org/10.1002/chin.201335229.

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37

Ameram, Nadiah, and Farook Adam. "Crystal structure of 2-methyl-N-{[2-(pyridin-2-yl)ethyl]carbamothioyl}benzamide." Acta Crystallographica Section E Crystallographic Communications 71, no. 9 (August 6, 2015): o636. http://dx.doi.org/10.1107/s2056989015013559.

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In the title compound, C16H17N3OS, a benzoyl thiourea derivative, the planes of the pyridine and benzene rings are inclined to one another by 66.54 (9)°. There is an intramolecular N—H...O hydrogen bond present forming anS(6) ring motif. In the crystal, molecules are linkedviapairs of N—H...N hydrogen bonds, forming inversion dimers, which are reinforced by pairs of C—H...S hydrogen bonds. The dimers are linkedviaC—H...π interactions, forming ribbons along [010].

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38

Vimala, G., N. Poomathi, P. T. Perumal, and A. SubbiahPandi. "Crystal structures of methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate and methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate." Acta Crystallographica Section E Crystallographic Communications 72, no. 2 (January 30, 2016): 261–65. http://dx.doi.org/10.1107/s2056989016001493.

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The title compounds, C19H16ClNO5, (I), and C19H15Cl2NO5, (II), both crystallize in the monoclinic space groupP21/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO2group in (I) but away from it in (II). In compound (I), the mean plane of the methyl acrylate unit is planar, with a maximum deviation of 0.0044 (2) Å for the methyl C atom, while in (II) this deviation is 0.0147 Å. The interplanar angles between the two aromatic rings are 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In both compounds, the methyl acrylate and nitrovinyl groups each adopt anEconformation about the C=C bond. In the crystal of (I), molecules are linked by C—H...O hydrogen bonds forming chains along thebaxis. The chains are linkedviaC—H...Cl hydrogen bonds, forming sheets parallel to theabplane. The sheets are linkedviaC—H...π interactions, forming a three-dimensional structure. In the crystal of (II), molecules are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers with anR22(30) ring motif. The dimers are linkedviaC—H...O hydrogen bonds, forming sheets parallel to theacplane and enclosingR44(28) ring motifs. The sheets are linkedviaparallel slipped π–π interactions (intercentroid distances are bothca3.86 Å), forming a three-dimensional structure.

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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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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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41

Xu, Yu-Xing, Wei-Ji Hu, and Guo-Liang Zhao. "Crystal structure of methyl (E)-4-[2-(8-hydroxyquinolin-2-yl)vinyl]benzoate." Acta Crystallographica Section E Crystallographic Communications 72, no. 9 (August 5, 2016): 1251–53. http://dx.doi.org/10.1107/s205698901601210x.

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The title compound, C19H15NO3, was synthesized by a Perkin reaction of 2-methyl-8-hydroxyquinoline and 4-formyl-2-methylbenzoate in acetic anhydride under a nitrogen atmosphere. The molecule has anEconformation about the C=C bond, and the quinoline ring system and the benzene ring are inclined to one another by 29.22 (7)°. There is an intramolecular O—H...N hydrogen bond in the 8-hydroxyquinoline moiety. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with anR22(28) ring motif. The dimers are linked by C—H...O hydrogen bonds and C—H...π interactions, forming sheets parallel to plane (10-1).

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42

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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43

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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44

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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45

Sowmya, Narayanan Swarna, Yechuri Vidyalakshmi, Sadasivam Sampathkrishnan, Thothadri Srinivasan, and Devadasan Velmurugan. "Pyrrolidinium-2-carboxylate–4-nitrophenol (1/2)." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (October 31, 2013): o1723. http://dx.doi.org/10.1107/s1600536813028742.

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In the title compound, C5H9NO2·2C6H5NO3, the pyrrolidine ring of the pyrrolidinium-2-carboxylate zwitterion adopts a twisted conformation on the –CH2—CH2– bond adjacent to the N atom. The mean plane of this pyrrolidine ring forms dihedral angles of 25.3 (3) and 32.1 (3)° with the two nitrophenol rings. An intramolecular N—H...O hydrogen bond occurs in the pyrrolidinium-2-carboxylate molecule. In the crystal, molecules are linkedviaO—H...O and N—H...O hydrogen bonds, enclosingR32(8) ring motifs, forming chains running parallel to theaaxis. These chains are further cross-linked by O—H...O and C—H...O hydrogen bonds, forming undulating two-dimensional networks lying parallel to (001).

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Victoria, Antony Samy, Palaniyappan Sivajeyanthi, Natarajan Elangovan, Kasthuri Balasubramani, Thathan Kolochi, and Kanagasabapathy Thanikasalam. "Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hydroxy-3-methoxy-5-nitrobenzylidene)amino]benzoate." Acta Crystallographica Section E Crystallographic Communications 74, no. 8 (July 10, 2018): 1079–82. http://dx.doi.org/10.1107/s2056989018009465.

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The title Schiff base compound, C17H16N2O6, has an E configuration with respect to the C=N bond, with a dihedral angle between the two benzene rings of 31.90 (12)°. There is an intramolecular O—H...Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers enclosing an R 2 2(4) ring motif. The dimers are linked about an inversion centre by pairs of C—H...O hydrogen bonds, which enclose R 2 2(22) loops, forming chains propagating along the [10\overline{3}] direction. Hirshfeld surface analysis and fingerprint plots show enrichment ratios for the H...H, O...H and C...H contacts, indicating a high propensity of such interactions in the crystal. Both the nitro group and the CH3–CH2–O– group are positionally disordered.

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Ezhilarasi, K. S., D. Reuben Jonathan, R. Vasanthi, B. K. Revathi, and G. Usha. "Crystal structure of (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 30, 2015): o371—o372. http://dx.doi.org/10.1107/s2056989015008087.

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The molecular structure of the title compound, C21H18O4, consists of a 3,4-dimethoxyphenyl ring and a naphthalene ring system linkedviaa prop-2-en-1-one spacer. The molecule is almost planar, with a dihedral angle between the benzene ring and the naphthalene ring system of 2.68 (12)°. There is an intramolecular O—H...O hydrogen bond involving the adjacent hydroxy and carbonyl groups. The molecule has anEconformation about the C=C bond and the carbonyl group issynwith respect to the C=C bond. In the crystal, molecules are linked by bifurcated C—H...(O,O) hydrogen bonds, enclosing anR21(6) ring motif, and by a further C—H...O hydrogen bond, forming undulating sheets extending inb-andc-axis directions. There are π–π interactions between the sheets, involving inversion-related naphthalene and benzene rings [intercentroid distance = 3.7452 (17) Å], forming a three-dimensional structure.

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Howlader, M. B. H., M. S. Begum, M. C. Sheikh, R. Miyatake, and E. Zangrando. "Crystal structure ofS-hexyl (E)-3-(4-methylbenzylidene)dithiocarbazate." Acta Crystallographica Section E Crystallographic Communications 71, no. 2 (January 10, 2015): o103—o104. http://dx.doi.org/10.1107/s2056989015000080.

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In the title compound, C15H22N2S2, the dithiocarbazate group adopts anEconformation with respect to the C=N bond of the benzylidene moiety. 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...π interactions, forming chains propagating along [100].

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49

Yamuna, Thammarse S., Manpreet Kaur, Jerry P. Jasinski, and H. S. Yathirajan. "4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (May 24, 2014): o702—o703. http://dx.doi.org/10.1107/s1600536814011489.

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In the cation of the title salt, C8H13N4+·C4H3O4−, the piperazinium ring adopts a slightly distorteded chair conformation. In the crystal, a single strong O—H...O intermolecular hydrogen bond links the anions, forming chains along thec-axis direction. The chains of anions are linked by the cations,viaN—H...O hydrogen bonds, forming sheets parallel to (100). These layers are linked by weak C—H...O hydrogen bonds, forming a three-dimensional structure. In addition, there are weak π–π interactions [centroid–centroid distance = 3.820 (9) Å] present involving inversion-related pyrimidine rings.

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50

Nimthong-Roldán, Arunpatcha, Paramee Sripa, and Yupa Wattanakanjana. "Crystal structure of chlorido[1-(4-nitrophenyl)thiourea-κS]bis(triphenylphosphane-κP)silver(I)." Acta Crystallographica Section E Crystallographic Communications 73, no. 6 (May 9, 2017): 829–31. http://dx.doi.org/10.1107/s2056989017006405.

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In the title compound, [AgCl(C7H7N3O2S)(C18H15P)2], the AgIion is in a distorted tetrahedral coordination environment formed by P atoms from two triphenylphosphane ligands, one terminal S atom from the 1-(4-nitrophenyl)thiourea ligand and a chloride ion. In the crystal, bifurcated (N—H)2...Cl hydrogen bonds [with graph-set motifR21(6)] connect complex molecules, forming zigzag chains along [001]. These chains are linkedviaweak C—H...O hydrogen bonds, forming a two-dimensional network parallel to (100). An intramolecular N—H...Cl hydrogen bond forming anS(6) ring is also observed.

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Journal articles on the topic 'Bond forming'

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