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Journal articles on the topic 'C–X bond'

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Author: Grafiati

Published: 6 September 2023

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1

Xu, Da-Zhen, Ren-Ming Hu, and Yi-Huan Lai. "Iron-Catalyzed Aerobic Oxidative Cross-Dehydrogenative C(sp3)–H/X–H (X = C, N, S) Coupling Reactions." Synlett 31, no. 18 (July 21, 2020): 1753–59. http://dx.doi.org/10.1055/s-0040-1707195.

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The direct functionalization of C(sp3)–H bonds is an attractive research topic in organic synthetic chemistry. The cross-dehydrogenative coupling (CDC) reaction provides a simple and powerful tool for the construction of C–C and C–heteroatom bonds. Recently, some progress has been made in the iron-catalyzed aerobic oxidative CDC reactions. Here, we present recent developments in the direct functionalization of C(sp3)–H bonds catalyzed by simple iron salts with molecular oxygen as the terminal oxidant.1 Introduction2 C(sp3)–C Bond Formation3 C(sp3)–N Bond Formation4 C(sp3)–S(Se) Bond Formation5 Conclusion and Outlook

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2

Robertson, Katherine N., Osvald Knop, and T. Stanley Cameron. "C-H···H-C interactions in organoammonium tetraphenylborates: another look at dihydrogen bonds." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 727–43. http://dx.doi.org/10.1139/v03-080.

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The crystal structures of the tetraphenylborates of the dabcoH+, guanidinium (MeCN solvate), and biguanidinium cations are shown to contain a variety of C-H···H-C dihydrogen (DB) bonds of nominally zero polarity, as well as a variety of N-H···N, C-H···N, N-H···Ph, and C-H···Ph hydrogen (HB) bonds. These intermolecular bonds have been characterized topologically after multipole refinement of the structures. The coexistence of the DBs and HBs in each of the structures makes it possible to establish their relative strength hierarchy. It also illustrates the importance of the DBs in satisfying the tendency of these structures to maximize the total intermolecular bonding engagement. To compare the above DBs with other DBs, the results of an extensive set of MP2/6-31G(d,p) calculations (supplied by I. Alkorta) were analyzed for reference correlations between the bond-critical parameters. Thus, for an X-H···H-Y bond, the difference Δε(H)m between the Mulliken charges on the H atoms in the uncomplexed X-H and H-Y components correlates quite well with the X-H···H-Y parameters and can be used for predicting the topological strength of an X-H···H-Y bond. The use of the difference Δε(H)c in the bond does not appear to change the correlation significantly; closer correlations are observed when the amount of charge transferred on formation of the H···H bond is used instead of Δε(H)m or Δε(H)c. Bonding interactions are obtained even between like or symmetry-related H atoms as a consequence of induced-dipole interactions, which accounts for the existence of the above intermolecular C-H···H-C bonds with d(H···H) = 2.182.57 Å, electron density at the bond-critical point of ~0.050.08 e/Å3, and a rough estimate of the H···H binding energy of ~1-5 kcal/mol. Examination of the bond-critical parameters of X-H···H-Y bonds also suggests a criterion of stability of these bonds with respect to the transition from non-shared (closed-shell) X-H···H-Y interaction to covalent (shared-shell) X···H-H···Y interaction. This transition appears to be discontinuous.Key words: bond-critical parameters, bond topology, dihydrogen bonds, hydrogen bonds, organoammonium tetraphenylborates.

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3

Liu, Dong, Chao Liu, and Aiwen Lei. "Carbon-Centered Radical Addition to C=X Bonds for C−X Bond Formation." Chemistry - An Asian Journal 10, no. 10 (June 23, 2015): 2040–54. http://dx.doi.org/10.1002/asia.201500326.

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4

Valentini, Federica, Oriana Piermatti, and Luigi Vaccaro. "Metal and Metal Oxide Nanoparticles Catalyzed C–H Activation for C–O and C–X (X = Halogen, B, P, S, Se) Bond Formation." Catalysts 13, no. 1 (December 22, 2022): 16. http://dx.doi.org/10.3390/catal13010016.

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The direct functionalization of an inactivated C–H bond has become an attractive approach to evolve toward step-economy, atom-efficient and environmentally sustainable processes. In this regard, the design and preparation of highly active metal nanoparticles as efficient catalysts for C–H bond activation under mild reaction conditions still continue to be investigated. This review focuses on the functionalization of un-activated C(sp3)–H, C(sp2)–H and C(sp)–H bonds exploiting metal and metal oxide nanoparticles C–H activation for C–O and C–X (X = Halogen, B, P, S, Se) bond formation, resulting in more sustainable access to industrial production.

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5

Allwohn, Jürgen, Ralf Hunold, Monika Pilz, Rolf-Günter Müller, Werner Massa, and Armin Berndt. "Nachweis starker C – Sn-Hyperkonjugation über Kristallstruktur und NMR-Daten eines C-Stannylmethylenborans / Evidence for Strong C–Sn-Hyperconjugation by Crystal Structure and NMR Data of a C-Stannylmethyleneborane." Zeitschrift für Naturforschung B 45, no. 3 (March 1, 1990): 290–98. http://dx.doi.org/10.1515/znb-1990-0304.

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Strong C—Sn hyperconjugation in C-stannylmethyleneborane 3 is indicated by (1) a small B—sp2C—Sn bond angle (105.6°), (2) a long sp2C—Sn bond (216 pm), (3) a very short B=C double bond (131 pm), (4) a very small coupling constant 1J(119Sn-13C) = 125 Hz for the sp2C—Sn bond and (5) shielding of the boron atom of the B=C double bond by 20 ppm as compared to methyleneboranes without strong hyperconjugation. The boron atoms of the B=C double bond of 3 and related methyleneboranes act as π-donor and σ-acceptor, the substituents X at the carbon atom of the B=C double bond as π-acceptors and, through their C—X σ-bonds, as σ-donors. The partly bridged methyleneborane 3 closes the gap between unbridged and bridged methyleneboranes. Relationships to non-classical carbocations are pointed out.

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6

Nagorny, Pavel, and Zhankui Sun. "New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation." Beilstein Journal of Organic Chemistry 12 (December 23, 2016): 2834–48. http://dx.doi.org/10.3762/bjoc.12.283.

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Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

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7

Liu, Dong, Chao Liu, and Aiwen Lei. "ChemInform Abstract: Carbon-Centered Radical Addition to C=X Bonds for C-X Bond Formation." ChemInform 46, no. 46 (October 27, 2015): no. http://dx.doi.org/10.1002/chin.201546253.

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8

Luo, Tian, Shanghui Tian, Jie-Ping Wan, and Yunyun Liu. "Recent Advances in Transition Metal-Free Halogenation of C(sp2)-H Bonds." Current Organic Chemistry 25, no. 10 (June 1, 2021): 1180–93. http://dx.doi.org/10.2174/1385272825666210122094423.

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C-X (X = halogen) bonds are indispensable functional groups in organic synthesis by mediating a massive number of important organic reactions. While a variety of different catalytic strategies are available for generating C-X bonds, those methods enabling the C-X bond formation under transition metal-free conditions via the C-H bond functionalization are particularly interesting because of the inherent atom economy and environmental friendliness associated with such methods. Herein, the advancements in the transition metal-free halogenation of C(2)-H bond are reviewed.

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9

Hao, Wenyan, and Yunyun Liu. "C–H bond halogenation catalyzed or mediated by copper: an overview." Beilstein Journal of Organic Chemistry 11 (November 9, 2015): 2132–44. http://dx.doi.org/10.3762/bjoc.11.230.

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Carbon–halogen (C–X) bonds are amongst the most fundamental groups in organic synthesis, they are frequently and widely employed in the synthesis of numerous organic products. The generation of a C–X bond, therefore, constitutes an issue of universal interest. Herein, the research advances on the copper-catalyzed and mediated C–X (X = F, Cl, Br, I) bond formation via direct C–H bond transformation is reviewed.

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10

Liu, Nan-nan, and Yi-hong Ding. "A metal–metal bond passing through the arene ligand: a theoretical study on inverse sandwiches X[Sc–C8H8–Sc]nX (X = F, Cl, Br; n = 1, 2)." New Journal of Chemistry 39, no. 3 (2015): 1558–62. http://dx.doi.org/10.1039/c4nj01832j.

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In X[Sc–C₈H₈–Sc]₂X (X = F–Br), Sc–Sc bonds between two [Sc–C₈H₈–Sc] units and the Sc–Sc bond through C₈H₈ form the uninterrupted Sc–Sc–Sc–Sc bond-chain.

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11

Lykhach, Yaroslava, Viktor Johánek, Armin Neitzel, Tomáš Skála, Nataliya Tsud, Klára Beranová, Josef Mysliveček, Olaf Brummel, and Jörg Libuda. "Redox-mediated C–C bond scission in alcohols adsorbed on CeO_{2− x} thin films." Journal of Physics: Condensed Matter 34, no. 19 (March 3, 2022): 194002. http://dx.doi.org/10.1088/1361-648x/ac5138.

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Abstract The decomposition mechanisms of ethanol and ethylene glycol on well-ordered stoichiometric CeO2(111) and partially reduced CeO2−x (111) films were investigated by means of synchrotron radiation photoelectron spectroscopy, resonant photoemission spectroscopy, and temperature programmed desorption. Both alcohols partially deprotonate upon adsorption at 150 K and subsequent annealing yielding stable ethoxy and ethylenedioxy species. The C–C bond scission in both ethoxy and ethylenedioxy species on stoichiometric CeO2(111) involves formation of acetaldehyde-like intermediates and yields CO and CO2 accompanied by desorption of acetaldehyde, H2O, and H2. This decomposition pathway leads to the formation of oxygen vacancies. In the presence of oxygen vacancies, C–O bond scission in ethoxy species yields C2H4. In contrast, C–C bond scission in ethylenedioxy species on the partially reduced CeO2−x (111) is favored with respect to C–O bond scission and yields methanol, formaldehyde, and CO accompanied by the desorption of H2O and H2. Still, scission of C–O bonds on both sides of the ethylenedioxy species yields minor amounts of accompanying C2H4 and C2H2. C–O bond scission is coupled with a partial recovery of the lattice oxygen in competition with its removal in the form of water.

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12

Aguilar, David, Rafael Navarro, Tatiana Soler, and Esteban P. Urriolabeitia. "Regioselective functionalization of iminophosphoranes through Pd-mediated C–H bond activation: C–C and C–X bond formation." Dalton Transactions 39, no. 43 (2010): 10422. http://dx.doi.org/10.1039/c003241g.

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13

Marcos-Ayuso, Guillermo, Agustí Lledós, and Juan A. Casares. "Copper(i) activation of C–X bonds: bimolecular vs. unimolecular reaction mechanism." Chemical Communications 58, no. 16 (2022): 2718–21. http://dx.doi.org/10.1039/d1cc07027d.

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Two monomeric copper(i) complexes participate in the activation of an Ar–I bond. One of them weakens the C–I bond, while the other inserts in the bond. Paradoxically, only one copper(i) complex participates in the breaking of stronger Ar–Br bonds.

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14

Wang, Youliang, and Raymond A. Poirier. "Generalized valence bond study of rotational singlet structures and pi bond energies for systems containing C==C, Si==Si, and C==Si double bonds." Canadian Journal of Chemistry 76, no. 4 (April 1, 1998): 477–82. http://dx.doi.org/10.1139/v98-041.

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Ab initio GVB(6/12)/6-31G** calculations were performed on A2X==YB2 (A, B = H, F; X, Y = C, Si) to obtain the optimized geometries for planar and twisted singlet structures, and to also calculate pi bond energies (rotational barriers). The nature of C-C, Si-Si, and C-Si pi bonds has been investigated. The results show that the C-C pi bond energy (E pi (ethene) = 65.4 kcal/mol) decreases with increasing fluorine substitution. The pyramidalization at the carbon or silicon center for the twisted structures decreases the pi bond energies in the substituted ethenes and their silicon counterparts. The Si-Si (E pi (disilene) = 23.2 kcal/mol) and C-Si (E pi (silaethene) = 31.6 kcal/mol) pi bonds become much weaker. Fluorine substitution stabilizes both the diradical and the dipolar twisted singlet structures.Key words: pi bond energy, ab initio calculations, generalized valence bond, fluorine substitution, disilene, and silaethene.

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15

Yan, Guobing, Xiangmei Wu, and Minghua Yang. "Transition-metal-catalyzed additions of C–H bonds to C–X (X = N, O) multiple bonds via C–H bond activation." Organic & Biomolecular Chemistry 11, no. 34 (2013): 5558. http://dx.doi.org/10.1039/c3ob40652k.

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16

Banerjee, Arghya, Satavisha Sarkar, and Bhisma K. Patel. "C–H functionalisation of cycloalkanes." Organic & Biomolecular Chemistry 15, no. 3 (2017): 505–30. http://dx.doi.org/10.1039/c6ob01975g.

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17

Han, Ying-Feng, and Guo-Xin Jin. "Cyclometalated [Cp*M(C^X)] (M = Ir, Rh; X = N, C, O, P) complexes." Chem. Soc. Rev. 43, no. 8 (2014): 2799–823. http://dx.doi.org/10.1039/c3cs60343a.

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Isolated and well-defined cyclometalated iridium/rhodium complexes that contain a Cp*M–C (M = Ir, Rh) bond stabilised by the intramolecular coordination of neutral donor atoms (N, C, O or P), together with their applications, were summarized.

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18

Gao, Han, Lingfei Hu, Yanlei Hu, Xiangying Lv, Yan-Bo Wu, and Gang Lu. "Origins of Lewis acid acceleration in nickel-catalysed C–H, C–C and C–O bond cleavage." Catalysis Science & Technology 11, no. 13 (2021): 4417–28. http://dx.doi.org/10.1039/d1cy00660f.

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19

Parra, Rubén D., and Sławomir J. Grabowski. "Enhancing Effects of the Cyano Group on the C-X∙∙∙N Hydrogen or Halogen Bond in Complexes of X-Cyanomethanes with Trimethyl Amine: CH3−n(CN)nX∙∙∙NMe3, (n = 0–3; X = H, Cl, Br, I)." International Journal of Molecular Sciences 23, no. 19 (September 25, 2022): 11289. http://dx.doi.org/10.3390/ijms231911289.

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In this paper, density functional theory and wave function theory calculations are carried out to investigate the strength and nature of the intermolecular C-X∙∙∙N bond interaction as a function of the number of cyano groups, CN, in the X-bond donor while maintaining the X-bond acceptor as fixed. Specifically, complexes of X-cyanomethanes with trimethyl amine CH3−n(CN)nX∙∙∙NMe3 (n = 0–3; X = H, Cl, Br, I) are used as model systems. Geometrical parameters and vibrational C-X-stretching frequencies as well as interaction energies are used as relevant indicators to gauge hydrogen or halogen bond strength in the complexes. Additional characteristics of interactions that link these complexes, i.e., hydrogen or halogen bonds, are calculated with the use of the following theoretical tools: the atoms in molecules (AIM) approach, the natural bond orbital (NBO) method, and energy decomposition analysis (EDA). The results show that, for the specified X-center, the strength of C-X∙∙∙N interaction increases significantly and in a non-additive fashion with the number of CN groups. Moreover, the nature (noncovalent or partly covalent) of the interactions is revealed via the AIM approach.

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20

Linden, Anthony, Yuehui Zhou, and Heinz Heimgartner. "Intra- and intermolecular Se...X (X = Se, O) interactions in selenium-containing heterocycles: 3-benzoylimino-5-(morpholin-4-yl)-1,2,4-diselenazole." Acta Crystallographica Section C Structural Chemistry 70, no. 5 (April 18, 2014): 482–87. http://dx.doi.org/10.1107/s2053229614008237.

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In the selenium-containing heterocyclic title compound {systematic name: N-[5-(morpholin-4-yl)-3H-1,2,4-diselenazol-3-ylidene]benzamide}, C13H13N3O2Se2, the five-membered 1,2,4-diselenazole ring and the amide group form a planar unit, but the phenyl ring plane is twisted by 22.12 (19)° relative to this plane. The five consecutive N—C bond lengths are all of similar lengths [1.316 (6)–1.358 (6) Å], indicating substantial delocalization along these bonds. The Se...O distance of 2.302 (3) Å, combined with a longer than usual amide C=O bond of 2.252 (5) Å, suggest a significant interaction between the amide O atom and its adjacent Se atom. An analysis of related structures containing an Se—Se...X unit (X = Se, S, O) shows a strong correlation between the Se—Se bond length and the strength of the Se...X interaction. When X = O, the strength of the Se...O interaction also correlates with the carbonyl C=O bond length. Weak intermolecular Se...Se, Se...O, C—H...O, C—H...π and π–π interactions each serve to link the molecules into ribbons or chains, with the C—H...O motif being a double helix, while the combination of all interactions generates the overall three-dimensional supramolecular framework.

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21

Odoko, Mamiko, Min Yao, Eiki Yamashita, Ryosuke Nakashima, Kunio Hirata, Hiroshi Aoyama, Kazumasa Muramoto, Kyoko Shinzawa-Itoh, Shinya Yoshikawa, and Tomitake Tsukihara. "Optimization of the energy constant of the methionine Sδ—C∊bond forX-PLORrefinement of protein structure." Journal of Applied Crystallography 34, no. 1 (February 1, 2001): 80–81. http://dx.doi.org/10.1107/s0021889800019944.

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The bond energy constant of methionine Sδ—C∊, 170.066 kcal mol−1 Å−2, is given as a default value in X-ray protein structure refinement withX-PLOR[Brünger (1992).X-PLOR Version 3.1. A system for X-ray Crystallography and NMR. New York University Press]. When the atomic parameters of 3564 amino acid residues of bovine heart cytochromecoxidase were refined at 2.0 Å resolution by usingX-PLORwith default restraining parameters, 36 bond lengths deviated by over 0.06 Å from their ideal values. Out of the 36 bonds, 25 were methionine Sδ—C∊bonds. Refinement with an energy parameter of 500.0 kcal mol−1 Å−2for the methionine Sδ—C∊bond resulted in convergence of the Sδ—C∊bond lengths to within 0.06 Å from their ideal values and reduced the crystallographicRand free-Rfactors by 0.6 and 0.3%, respectively. Consequently, a strong bond energy constant for Sδ—C∊of 500.0 kcal mol−1 Å−2is recommended instead of the default value of 170.066 kcal mol−1 Å−2.

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22

Liu, Wen-Bo, Muhammad Usman, and Xiao-Wen Zhang. "Silicon-Tethered Frameworks as Directing Groups for Carbon–Carbon and Carbon–Heteroatom Bond Formation." Synthesis 51, no. 07 (March 5, 2019): 1529–44. http://dx.doi.org/10.1055/s-0037-1612123.

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Recent advances in the use of silicon-tethered frameworks as directing groups for the efficient construction of C–C, C–B, C–O and C–X (X = halogen) bonds are discussed in this short review. In addition, mechanistic insights are briefly discussed. Hence, the goal of this short review is to give an overview of the state of the art in this field, encompassing the reactivity, selectivity and efficiency of different processes.1 Introduction2 Carbon–Carbon Bond Formation2.1 Alkenylation2.2 Arylation2.3 Carbonylation3 Carbon–Boron Bond Formation4 Carbon–Oxygen and Carbon–Halogen Bond Formation5 Conclusion

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23

Li, Chong, Juan Wang, and Shang-Dong Yang. "Visible-light-facilitated P-center radical addition to CX (X = C, N) bonds results in cyclizations." Chemical Communications 57, no. 65 (2021): 7997–8002. http://dx.doi.org/10.1039/d1cc02604f.

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24

Wang, Yi, Anan Liu, Dongge Ma, Shuhong Li, Chichong Lu, Tao Li, and Chuncheng Chen. "TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions." Catalysts 8, no. 9 (August 27, 2018): 355. http://dx.doi.org/10.3390/catal8090355.

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Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

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25

Yan, Guobing, Xiangmei Wu, and Minghua Yang. "ChemInform Abstract: Transition-Metal-Catalyzed Additions of C-H Bonds to C-X (X = N, O) Multiple Bonds via C-H Bond Activation." ChemInform 44, no. 44 (October 14, 2013): no. http://dx.doi.org/10.1002/chin.201344232.

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26

Zeng, Qingle, Fuhai Li, and Xianjie Yin. "Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts." AIMS Molecular Science 10, no. 3 (2023): 153–70. http://dx.doi.org/10.3934/molsci.2023011.

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<abstract> <p>Amines are abundant in natural product chemistry and are readily available chemical raw materials. The C-N bonds of amines are difficult to break due to the large C-N bond energy. In recent years, chemists have developed a variety of activation methods for amino groups of amines. Among these reported methods, to convert amines into quaternary ammonium salts is preferred, for quaternary ammonium salts are readily available and stable. In recent years, great progress has been achieved in the study of transition metal-catalyzed construction of various C-X bonds involving aromatic amines and benzyl amines-derived quaternary ammonium salts by cleavage of C-N bonds. This review describes the transition metal-catalyzed reaction of quaternary ammonium salts to construct C-X bonds by cleavage of C-N bond. Moreover, if chiral benzylamines-derived quaternary ammonium salts are used, a variety of highly enantiomeric pure chiral organic compounds can also be obtained. The chirality of quaternary ammonium salts remained good in the products and all reactions underwent S<sub>N</sub>2-type configuration inversion.</p> </abstract>

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27

Yu, Bangkui, and Hanmin Huang. "Recent Advances in C—X Bond Metathesis Reactions." Chinese Journal of Organic Chemistry 42, no. 8 (2022): 2376. http://dx.doi.org/10.6023/cjoc202202003.

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28

Ahmad, Muhammad Siddique, Po-Han Lin, Qing Zhang, Bing Zeng, Qifeng Wang, and Kamel Meguellati. "Visible Light Induced C-H/N-H and C-X Bonds Reactions." Reactions 4, no. 1 (March 2, 2023): 189–230. http://dx.doi.org/10.3390/reactions4010012.

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Herein, we report efficient visible light-induced photoredox reactions of C–H/N–H and C–X Bonds. These methods have provided access to varied portfolio of synthetically important γ-ketoesters, azaspirocyclic cyclohexadienones spirocyclohexadienones, multisubstituted benzimidazole derivatives, substituted N,2-diarylacetamide, 2-arylpyridines and 2-arylquinolines in good yields and under mild conditions. Moreover, we have successfully discussed the construction through visible light-induction by an intermolecular radical addition, dearomative cyclization, aryl migration and desulfonylation. Similarly, we also spotlight the visible light-catalyzed aerobic C–N bond activation from well-known building blocks through cyclization, elimination and aromatization. The potential use of a wide portfolio of simple ketones and available primary amines has made this transformation very attractive.

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29

Orellana, Arturo, and Andrei Nikolaev. "Transition-Metal-Catalyzed C–C and C–X Bond-Forming Reactions Using Cyclopropanols." Synthesis 48, no. 12 (May 18, 2016): 1741–68. http://dx.doi.org/10.1055/s-0035-1560442.

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30

Yuan, Kun, Hui Xue Li, Huian Tang, and Yuan Cheng Zhu. "Density Function Theory Study on the Recognition of the Urea-Based Involving Bromine Derivation Receptor for the Halogen Anions." Applied Mechanics and Materials 328 (June 2013): 850–54. http://dx.doi.org/10.4028/www.scientific.net/amm.328.850.

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The recognition mechanism of the urea-based involving Br derivation receptor (A) for the halogen anions through hydrogen bond and halogen bond was discussed by the density function Becke, three-parameter, Lee-Yang-Parr (B3LYP) method. The results showed that the guest-host recognition was performed by using four coordination weak bonds, which include two N-H...X hydrogen bonds and two C-Br...X halogen bonds (X= F-,Cl-,Br- and I-). The calculated interaction energies (ΔECP) with basis set super-position error (BSSE) correction of the four systems are-3.95, -82.43, -70.86 and 992.63 kJmol-1, respectively. So, the urea-based derivation receptor (A) presents the best recognition capable for the Br- and Cl-, and it can not recognize the I- in the same condition. Natural bond orbital theory (NBO) analysis has been used to investigate the electronic behavior and property of the red-shift N-H...X hydrogen bonds and two blue-shift C-Br...X halogen bonds in the A...X- systems.

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31

Quentin, Jay, Eric W. Reinheimer, and Leonard R. MacGillivray. "Halogen-Bond Mediated [2+2] Photodimerizations: À la Carte Access to Unsymmetrical Cyclobutanes in the Solid State." Molecules 27, no. 3 (February 3, 2022): 1048. http://dx.doi.org/10.3390/molecules27031048.

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The ditopic halogen-bond (X-bond) donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene (1,2-, 1,3-, and 1,4-di-I-tFb, respectively) form binary cocrystals with the unsymmetrical ditopic X-bond acceptor trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene (2,4-bpe). The components of each cocrystal (1,2-di-I-tFb)·(2,4-bpe), (1,3-di-I-tFb)·(2,4-bpe), and (1,4-di-I-tFb)·(2,4-bpe) assemble via N···I X-bonds. For (1,2-di-I-tFb)·(2,4-bpe) and (1,3-di-I-tFb)·(2,4-bpe), the X-bond donor supports the C=C bonds of 2,4-bpe to undergo a topochemical [2+2] photodimerization in the solid state: UV-irradiation of each solid resulted in stereospecific, regiospecific, and quantitative photodimerization of 2,4-bpe to the corresponding head-to-tail (ht) or head-to-head (hh) cyclobutane photoproduct, respectively.

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32

Baillargeon, Pierre, Tarik Rahem, Édouard Caron-Duval, Jacob Tremblay, Cloé Fortin, Étienne Blais, Victor Fan, Daniel Fortin, and Yves L. Dory. "Isomorphous crystal structures of chlorodiacetylene and iododiacetylene derivatives: simultaneous hydrogen and halogen bonds on carbonyl." Acta Crystallographica Section E Crystallographic Communications 73, no. 8 (July 17, 2017): 1175–79. http://dx.doi.org/10.1107/s2056989017010155.

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The crystal structures of tert-butyl (5-chloropenta-2,4-diyn-1-yl)carbamate, C10H12ClNO2 (II), and tert-butyl (5-iodopenta-2,4-diyn-1-yl)carbamate, C10H12INO2 (IV), are isomorphous to previously reported structures and accordingly their molecular and supramolecular structures are similar. In the crystals of (II) and (IV), molecules are linked into very similar two-dimensional wall organizations with antiparallel carbamate groups involved in a combination of hydrogen and halogen bonds (bifurcated N—H...O=C and C[triple-bond]C—X...O=C interactions on the same carbonyl group). There is no long-range parallel stacking of diynes, so the topochemical polymerization of diacetylene is prevented. A Cambridge Structural Database search revealed that C[triple-bond]C—X...O=C contacts shorter than the sum of the van der Waals radii are scarce (only one structure for the C[triple-bond]C—Cl...O=C interaction and 13 structures for the similar C[triple-bond]C—I...O=C interaction).

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33

Yang, Qi, Zongbin Jia, Longji Li, Long Zhang, and Sanzhong Luo. "Visible-light promoted arene C–H/C–X lactonizationviacarboxylic radical aromatic substitution." Organic Chemistry Frontiers 5, no. 2 (2018): 237–41. http://dx.doi.org/10.1039/c7qo00826k.

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34

Girgis, Adel S., Marian N. Aziz, ElSayed M. Shalaby, Fahmy M. Asaad, and I. S. Ahmed Farag. "Synthesis and X-ray Studies of Novel Azaphenanthrenes." Journal of Chemical Research 42, no. 2 (February 2018): 90–95. http://dx.doi.org/10.3184/174751918x15183538282993.

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Two azaphenanthrenes were synthesised by a facile synthetic pathway and characterised by X-ray crystallography. Molecular packing of 4-(2,4-dichlorophenyl)-2-methoxy-5,6-dihydrobenzo[ h]quinoline-3-carbonitrile exhibits C–H…N and C–H…Cl hydrogen bonds in addition to intermolecular C–H…π, Cl…π and π…π (π-ring) stacking interactions. However, molecules of the 2-ethoxy derivative are linked into chains by one hydrogen bond of the C–H…N type and the crystal structure reveals an intermolecular C–H…π (π-ring) interaction. Computational studies by AM1, PM3, and density functional theory (DFT) techniques provide good approximations to the experimental X-ray data. The root mean square errors between the experimental and calculated bond lengths using AM1, PM3 and DFT methods for the 2-methoxy and 2-ethoxy derivatives are 0.0187, 0.0193, 0.0120 and 0.0197, 0.0195 and 0.0116 respectively.

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35

Liu, Tao, Guo-Dong Liu, and Zhang-Yu Yu. "Ab initio study of hydrogen bond complexes of ring compounds containing the H2N-C=Y moiety with water." Open Chemistry 8, no. 5 (October 1, 2010): 1117–26. http://dx.doi.org/10.2478/s11532-010-0088-x.

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AbstractAb initio calculations, including natural charge population and natural resonance theory analyses, have been carried out to study the two-way effects between hydrogen bonds (H-bonds) and the intramolecular resonance effect by using the H-bonded complexes of ring compounds containing the H2N-C=Y moiety (C=Y bond is contained in the six-membered or five-membered rings) with water as models. The amino groups in the four monomers of ring compounds (FAYs, Y represents the heavy atoms in the substituent groups, =CH, =N, =SiH, and =P, respectively) can all serve as H-bond donors (HD) and H-bond acceptors (HA) to form stable H-bonded complexes with water. The HD H-bond and resonance effect enhance each other (positive two-way effects) whereas the HA H-bond and resonance effect weaken each other (negative two-way effects). The resonance effect in FAY(1) (C=Y bond is contained in the six-membered rings) is weaker than that in formamide, and those in FAY(2) and FAY(3) (C=Y bonds are contained in the five-membered rings). The two-way effects between H-bond and resonance effect exist in the H-bonded complexes of ring compounds containing the H2N-C=Y moiety with water.

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36

Mani, Devendra, and Elangannan Arunan. "The X–C···π (X = F, Cl, Br, CN) Carbon Bond." Journal of Physical Chemistry A 118, no. 43 (October 20, 2014): 10081–89. http://dx.doi.org/10.1021/jp507849g.

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37

Li, Wan-Di, Jia-Shuo Zhang, Lin-Yan Zhang, Zhong-Wen Liu, Juan Fan, and Xian-Ying Shi. "Rhodium-Catalyzed Alkylation of Aromatic Ketones with Allylic Alcohols and α,β-Unsaturated Ketones." Catalysts 13, no. 8 (July 26, 2023): 1157. http://dx.doi.org/10.3390/catal13081157.

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The direct transition-metal-catalyzed addition of C–H bonds to unsaturated C=X (X=C, O, and N) bonds via C–H bond activation has been recognized as a powerful tool for the construction of C–C bonds (in terms of atom and step economy). Herein, the direct rhodium-catalyzed C–H bond addition of aromatic ketones to allylic alcohols and α,β-unsaturated ketones that affords β-aryl carbonyl compounds is described, in which a ketone carbonyl acts as a weakly coordinating directing group. It was found that the type of alkyl in aromatic ketones is crucial for the success of the reaction. This transformation provides a convenient and efficient methodology for the synthesis of 2-alkyl aromatic ketones in moderate-to-excellent yields.

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38

Thimme Gowda, B., K. Jyothi, Jozef Kožíšek, and Hartmut Fuess. "Crystal Structure Studies on p-Substitutedbenzenesulphonamides 4-X-C6H4SO2NH2 (X = CH3, NH2 F, Cl or Br)." Zeitschrift für Naturforschung A 58, no. 11 (November 1, 2003): 656–60. http://dx.doi.org/10.1515/zna-2003-1110.

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Effect of ring substitution on the crystal structures of p-substitutedbenzenesulphonamides, p-XC6H4SO2NH2 (X = F, Cl, Br, CH3 or NH2) has been studied by determining the crystal structures of 4-chlorobenzenesulphonamide (4-ClC6H4SO2NH2) and 4-bromobenzenesulphonamide (4-BrC6H4SO2NH2) and analyzing the results along with the structures of 4-methylbenzenesulphonamide (4-CH3C6H4SO2NH2), 4-fluorobenzene-sulphonamide (4-FC6H4SO2NH2) and 4-aminobenzenesulphonamide (4-NH2C6H4SO2NH2). The crystal type, space group, formula units and lattice constants in Å of new structures are: (4-ClC6H4SO2NH2); monoclinic, P21/n, Z = 4, a = 6.6276(10), b = 16.219(3), c = 7.5716(10), β = 93.387(14)°; (4-BrC6H4SO2NH2): monoclinic, P 21/n, Z = 4, a = 6.5660(10), b = 16.4630(10), c = 7.6900(10), β = 92.760(10)°. Orientation of the amine group with respect to the phenyl ring is given by the torsion angles C(2)-C(1)-S-N: 70.9° and C(6)-C(1)-S-N: −108.5°. Similarly, the orientation of S, O(1) and O(2) with respect to the ring are given by torsion angles. The comparison of bond lengths and bond angles of 4-fluoro-, 4-chloro-, 4-bromo-, 4-methyl- and 4-amino-benzenesulphonamides reveal that the S-N and C-S bond lengths decrease with the introduction of electron-withdrawing substituents such as F, Cl or Br, while these groups do not have significant effects on the S-O distances. The effect on ring C-C distances was not uniform. Substitution of F, Cl or Br decreases the O-S-N bond angle, but increases the O-S-N, N-S-C(1) and C(3)-C(4)-C(5) bond angles.

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39

Fiore, Vito A., and Gerhard Maas. "Phospha-Michael reaction of tertiary phosphanes Ph2P–X (X=SiMe3, Cl) and N-triflyl-propiolamides." Zeitschrift für Naturforschung B 74, no. 9 (September 25, 2019): 671–76. http://dx.doi.org/10.1515/znb-2019-0100.

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AbstractThe uncatalyzed silylphosphanylation of acetylenic N-trifluoromethylsulfonyl-carboxamides by Ph2P–SiMe3, formally an insertion of a C,C triple bond into a P–Si bond, is reported. Some characteristic functional group transformations of the resulting 3-PPh2-2-SiMe3-N-triflyl-acrylamides were briefly explored: transamidation of the N-triflylamide group with allylamine, P oxidation and protodesilylation. A hydrophosphorylation of the acetylenic triple bond with chloro(diphenyl)phosphane is also reported.

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40

Tang, Ting-Hua, and Yun-Ping Cui. "A theoretical study of some hydrogen-bonded complexes using the theory of atoms in molecules." Canadian Journal of Chemistry 74, no. 6 (June 1, 1996): 1162–70. http://dx.doi.org/10.1139/v96-130.

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π-Type hydrogen-bonded complexes consisting of hydrogen halide HX (X = Cl, F) and the carbon–carbon triple or double bond of vinyl acetylene (1-buten-3-yne, HC≡C-CH=CH2) have been studied. The vinyl acetylene molecule contains two possible π-bonding sites (C≡C and C=C). It offers three possible structures of [Formula: see text] that comprise two T-type bonds to C≡C (endo and exo approaches) and one T-type bond to C=C (perpendicular approach). The optimized geometries and the hydrogen-bond stabilization energies, based on MP2(FULL)/6-311 ++ G(d,p)//6-31G(d,p) calculations, indicate that the π-type hydrogen bond to a C≡C triple bond leads to a more stable complex than for an analogous bond to C=C. The calculated global minima for the complexes with HF and HCl correspond to the H—X moiety lying along a bisector of the C≡C triple bond in the endo approach, predictions that are in good agreement with the reported FTMS results. The topological properties of the electron density distributions of these two systems have been analyzed in terms of the theory of atoms in molecules. The nature of π-type hydrogen bonds has also been discussed using the Laplacian of the electron density, [Formula: see text] The complexes [Formula: see text] and [Formula: see text] as well as the hydrogen-bonded complex consisting of 2-butyne (CH3-C≡C-CH3) and HCl were also studied for comparison. Key words: ab initio calculation, hydrogen bonding, topological analysis of electron density, vinyl acetylene, 2-butyne.

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41

Purnachandar, Dalovai, Kanaparthy Suneel, Sridhar Balasubramanian, and Galla V. Karunakar. "Gold–carbene assisted formation of tetraarylmethane derivatives: double X–H activation by gold." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4856–64. http://dx.doi.org/10.1039/c9ob00470j.

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An efficient gold–carbene promoted generation of tetraarylmethane derivatives from enynones and indoles was accomplished by the formation of a new C–O bond and two C–C bonds. It is significant that addition of two nucleophiles resulted the desired compounds.

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42

Borpatra, Paran J., Bhaskar Deka, Mohit L. Deb, and Pranjal K. Baruah. "Recent advances in intramolecular C–O/C–N/C–S bond formation via C–H functionalization." Organic Chemistry Frontiers 6, no. 20 (2019): 3445–89. http://dx.doi.org/10.1039/c9qo00863b.

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43

Quentin, Jay, Dale C. Swenson, and Leonard R. MacGillivray. "Supramolecular Sandwiches: Halogen-Bonded Coformers Direct [2+2] Photoreactivity in Two-Component Cocrystals." Molecules 25, no. 4 (February 18, 2020): 907. http://dx.doi.org/10.3390/molecules25040907.

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The halogen-bond (X-bond) donors 1,3- and 1,4-diiodotetrafluorobenzene (1,3-di-I-tFb and 1,4-di-I-tFb, respectively) form cocrystals with trans-1,2-bis(2-pyridyl)ethylene (2,2′-bpe) assembled by N···I X-bonds. In each cocrystal, 2(1,3-di-I-tFb)·2(2,2′-bpe) and (1,4-di-I-tFb)·(2,2′-bpe), the donor molecules support the C=C bonds of 2,2′-bpe to undergo an intermolecular [2+2] photodimerization. UV irradiation of each cocrystal resulted in stereospecific and quantitative conversion of 2,2′-bpe to rctt-tetrakis(2-pyridyl)cyclobutane (2,2′-tpcb). In each case, the reactivity occurs via face-to-face π-stacked columns wherein nearest-neighbor pairs of 2,2′-bpe molecules lie sandwiched between X-bond donor molecules. Nearest-neighbor C=C bonds are stacked criss-crossed in both cocrystals. The reactivity was ascribed to the olefins undergoing pedal-like motion in the solid state. The stereochemistry of 2,2′-tpcb is confirmed in cocrystals 2(1,3-di-I-tFb)·(2,2′-tpcb) and (1,4-di-I-tFb)·(2,2′-tpcb).

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44

Grabowsky, Simon, Manuela Weber, Jürgen Buschmann, and Peter Luger. "Experimental electron density study of ethylene oxide at 100 K." Acta Crystallographica Section B Structural Science 64, no. 3 (May 15, 2008): 397–400. http://dx.doi.org/10.1107/s0108768108010197.

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The experimental electron density of ethylene oxide was derived from a multipole refinement of 100 K X-ray data and complemented by density-functional calculations at experimental and optimized geometry. Atomic and bond-topological properties were derived using the atoms-in-molecules (AIM) formalism. The high strain in the three-membered ring molecule is mainly expressed by the high ellipticities of the three bonds in this ring, while the bond paths are only slightly bent for the C—C bond, but are virtually straight for the C—O bond.

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45

Starynowicz, Przemysław, Sławomir Berski, Nurbey Gulia, Karolina Osowska, Tadeusz Lis, and Sławomir Szafert. "Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in p-CH3CH2COC6H4-C≡C-C≡C-p-C6H4COCH3CH2." Molecules 25, no. 19 (September 24, 2020): 4388. http://dx.doi.org/10.3390/molecules25194388.

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The electron density of p-CH3CH2COC6H4-C≡CC≡C-p-C6H4COCH3CH2 has been investigated on the basis of single-crystal X-ray diffraction data collected to high resolution at 100 K and from theoretical calculations. An analysis of the X-ray data of the diyne showed interesting “liquidity” of electron distribution along the carbon chain compared to 1,2-diphenylacetylene. These findings are compatible with the results of topological analysis of Electron Localization Function (ELF), which has also revealed a larger (than expected) concentration of the electron density at the single bonds. Both methods indicate a clear π-type or “banana” character of a single bond and a significant distortion from the typical conjugated structure of the bonding in the diyne with a small contribution of cumulenic structures.

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46

Lu, Norman, Rong-Jyun Wei, Hsing-Fang Chiang, Joseph S. Thrasher, Yuh-Sheng Wen, and Ling-Kang Liu. "Weak hydrogen and halogen bonding in 4-[(2,2-difluoroethoxy)methyl]pyridinium iodide and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide." Acta Crystallographica Section C Structural Chemistry 73, no. 9 (August 7, 2017): 682–87. http://dx.doi.org/10.1107/s2053229617011172.

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To enable a comparison between a C—H...X hydrogen bond and a halogen bond, the structures of two fluorous-substituted pyridinium iodide salts have been determined. 4-[(2,2-Difluoroethoxy)methyl]pyridinium iodide, C8H10F2NO+·I−, (1), has a –CH2OCH2CF2H substituent at the para position of the pyridinium ring and 4-[(3-chloro-2,2,3,3-tetrafluoropropoxy)methyl]pyridinium iodide, C9H9ClF4NO+·I−, (2), has a –CH2OCH2CF2CF2Cl substituent at the para position of the pyridinium ring. In salt (1), the iodide anion is involved in one N—H...I and three C—H...I hydrogen bonds, which, together with C—H...F hydrogen bonds, link the cations and anions into a three-dimensional network. For salt (2), the iodide anion is involved in one N—H...I hydrogen bond, two C—H...I hydrogen bonds and one C—Cl...I halogen bond; additional C—H...F and C—F...F interactions link the cations and anions into a three-dimensional arrangement.

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47

Murata, M. "ChemInform Abstract: C-B and C-Si Bond-Forming Reactions of C-X Electrophiles." ChemInform 44, no. 35 (August 8, 2013): no. http://dx.doi.org/10.1002/chin.201335228.

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48

Singh, Pallavi, Kishor Kumar Chouhan, and Arup Mukherjee. "Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview." Chemistry – An Asian Journal 16, no. 17 (August 4, 2021): 2392–412. http://dx.doi.org/10.1002/asia.202100513.

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49

Engberts, J. B. F. N., Th A. J. W. Wajer, C. Kruk, and Th J. de Boer. "C-nitroso compounds. Part X: C-nitroso compounds as hydrogen bond acceptors." Recueil des Travaux Chimiques des Pays-Bas 88, no. 7 (September 2, 2010): 795–800. http://dx.doi.org/10.1002/recl.19690880704.

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50

Markó, István E., and M. Lakshmi Kantam. "Catalytic CC bond formation using triorganothallium reagents." Tetrahedron Letters 32, no. 20 (May 1991): 2255–58. http://dx.doi.org/10.1016/s0040-4039(00)79695-x.

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