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Journal articles on the topic 'Cyanocarbons'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Bruce, Michael I. "Some Organometallic Chemistry of Tetracyanoethene: CN-displacement and Cycloaddition Reactions with Alkynyl - Transition Metal Complexes and Related Chemistry." Australian Journal of Chemistry 64, no. 1 (2011): 77. http://dx.doi.org/10.1071/ch10307.

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The highly electron-deficient cyanocarbons tetracyanoethene (tcne) and, to a lesser extent, tetracyanoquinodimethane (tcnq), display a fascinating chemistry with transition metal substrates. In particular, the [2 + 2]-cycloadditions of the cyanocarbons with alkynyl- or poly-ynyl–metal complexes have been extensively studied by the author’s group. These reactions proceed via polar adducts to give σ-cyclobutenyl complexes, which then undergo facile ring-opening (retro-electrocyclic) reactions to form the corresponding butadienyl derivatives. In some cases, further reactions can occur by displacement of weakly bound ligands from the metal centre. The subsequent chemistry of these derivatives has been only cursorily investigated, while related studies of organic analogues have produced molecules with interesting electronic and optical properties.

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2

Arduengo III, Anthony J., Joseph C. Calabrese, William J. Marshall, Jason W. Runyon, Christian Schiel, Christoph Schinnen, Matthias Tamm, and Yosuke Uchiyama. "Imidazol-2-ylidene Reactivity towards Cyanocarbons." Zeitschrift für anorganische und allgemeine Chemie 641, no. 12-13 (September 3, 2015): 2190–98. http://dx.doi.org/10.1002/zaac.201500578.

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3

Webster, Owen W. "Cyanocarbons: A classic example of discovery-driven research." Journal of Polymer Science Part A: Polymer Chemistry 40, no. 2 (December 5, 2001): 210–21. http://dx.doi.org/10.1002/pola.10087.

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4

Hertler, W. R., W. Mahler, L. R. Melby, J. S. Miller, R. E. Putscher, and O. W. Webster. "Cyanocarbons—Their History From Conducting to Magnetic Organic Charge Transfer Salts." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 171, no. 1 (January 1989): 205–16. http://dx.doi.org/10.1080/00268948908065796.

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5

Berna, Patrick P., and Jerker Porath. "Cyanocarbons as ligands for electron donor acceptor chromatography of human serum proteins." Journal of Chromatography A 753, no. 1 (November 1996): 57–62. http://dx.doi.org/10.1016/s0021-9673(96)00515-8.

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6

Zhang, Xiuhui, Qianshu Li, Justin B. Ingels, Andrew C. Simmonett, Steven E. Wheeler, Yaoming Xie, R. Bruce King, Henry F. Schaefer III, and F. Albert Cotton. "Remarkable electron accepting properties of the simplest benzenoid cyanocarbons: hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene." Chemical Communications, no. 7 (2006): 758. http://dx.doi.org/10.1039/b515843e.

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7

Kałka, Andrzej J., Bartosz Mozgawa, Piotr Pietrzyk, and Andrzej M. Turek. "Intermolecular interactions of tetracyanoethylene (TCNE) and fumaronitrile (FN) with minor amines: A combined UV–Vis and EPR study." Journal of Chemical Physics 156, no. 9 (March 7, 2022): 094301. http://dx.doi.org/10.1063/5.0084088.

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In this paper, the nature of interactions between two cyanocarbons—tetracyanoethylene (TCNE) and fumaronitrile (FN)—and a series of four secondary amines possessing a general formula C4HxN (x = 5–11) is thoroughly scrutinized. For all of the TCNE–amine pairs, tricyanovinylation (TCV) reaction is observed; however, only for pyrrole, it is accompanied with a visible charge-transfer (CT) complex formation—no such chemical individuals, characteristic for TCNE, have been noticed for aliphatic and alicyclic amines. On the contrary, FN forms such complexes with all the amines studied. Interestingly, a rather unexpected reaction of FN with alicyclic amines has been observed. The recorded electron paramagnetic resonance (EPR) spectra indicate the presence of both TCNE●− and FN●− radicals in the analyzed samples, assigned to a complete charge (electron) transfer process within the CT complexes, whose efficiency can be additionally enhanced by photoirradiation. The origination of the former radical, whose presence is observed also in the TCNE–diethylamine mixture, is as well proposed to result indirectly from the TCV reaction, occurring for this system. Finally, the superhyperfine structure of EPR spectra, indicating the existence of some secondary interactions of the radicals with surrounding compounds, is discussed. Formation of CT complexes and tricyanovinylates has been investigated and characterized with UV–Vis spectroscopy, while the presence of (cyano)radicals in the analyzed mixtures has been evidenced by (photoinduced) EPR measurements. Interpretation of the experimental results is also supplemented with computer simulations including density functional theory calculations.

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8

Cariou, Monique, Michel Etienne, Jacques E. Guerchais, Rene Kergoat, and Marek M. Kubicki. "Transition metal-cyanocarbon chemistry." Journal of Organometallic Chemistry 327, no. 3 (July 1987): 393–401. http://dx.doi.org/10.1016/s0022-328x(00)99754-7.

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9

Kubicki, M. M., R. Kergoat, H. Scordia, L. C. Gomes de Lima, J. E. Guerchais, and P. L'Haridon. "Transition metal-cyanocarbon chemistry." Journal of Organometallic Chemistry 340, no. 1 (February 1988): 41–49. http://dx.doi.org/10.1016/0022-328x(88)80552-7.

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10

Kergoat, R., M. M. Kubicki, L. C. Gomes de Lima, H. Scordia, J. E. Guerchais, and P. L'Haridon. "Transition metal-cyanocarbon chemistry." Journal of Organometallic Chemistry 367, no. 1-2 (May 1989): 143–60. http://dx.doi.org/10.1016/0022-328x(89)87215-8.

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11

Dempsey Hyatt, I. F., Daniel J. Nasrallah, Michael A. Maxwell, A. Christina F. Hairston, Manahil M. Abdalhameed, and Mitchell P. Croatt. "Formation and in situ reactions of hypervalent iodonium alkynyl triflates to form cyanocarbenes." Chemical Communications 51, no. 25 (2015): 5287–89. http://dx.doi.org/10.1039/c4cc08676g.

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12

Jiang, Xinpeng, Zicong Zheng, Yan Gao, Deyou Lan, Wenhao Xu, Wang Zhang, and Guofei Chen. "Synthesis of tetrasubstituted alkenyl nitriles via cyanocarbene addition of [1.1.1]propellane." Organic Chemistry Frontiers 9, no. 8 (2022): 2234–39. http://dx.doi.org/10.1039/d2qo00186a.

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13

Yu, Huinan, Gordana Srdanov, Kobi Hasharoni, and Fred Wudl. "Decacyanooctatetraene dianion: A model system for cyanocarbon-based conjugated polymers." Tetrahedron 53, no. 45 (November 1997): 15593–602. http://dx.doi.org/10.1016/s0040-4020(97)00982-4.

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14

Berna, Patrick P., and Jerker Porath. "Salt-independent adsorption of human serum proteins on cyanocarbon gels." Journal of Chromatography B: Biomedical Sciences and Applications 693, no. 2 (June 1997): 277–85. http://dx.doi.org/10.1016/s0378-4347(97)00030-3.

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15

Maier, Günther, Hans Peter Reisenauer, and Katja Rademacher. "Cyanocarbene, Isocyanocarbene, and Azacyclopropenylidene: A Matrix-Spectroscopic Study." Chemistry - A European Journal 4, no. 10 (October 2, 1998): 1957–63. http://dx.doi.org/10.1002/(sici)1521-3765(19981002)4:10<1957::aid-chem1957>3.0.co;2-1.

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16

Kim, Jung-Soo, Sanjay K. S. Patel, Manish K. Tiwari, Chunfen Lai, Anurag Kumar, Young Sin Kim, Vipin Chandra Kalia, and Jung-Kul Lee. "Phe-140 Determines the Catalytic Efficiency of Arylacetonitrilase from Alcaligenes faecalis." International Journal of Molecular Sciences 21, no. 21 (October 23, 2020): 7859. http://dx.doi.org/10.3390/ijms21217859.

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Arylacetonitrilase from Alcaligenes faecalis ATCC8750 (NitAF) hydrolyzes various arylacetonitriles to the corresponding carboxylic acids. A systematic strategy of amino acid residue screening through sequence alignment, followed by homology modeling and biochemical confirmation was employed to elucidate the determinant of NitAF catalytic efficiency. Substituting Phe-140 in NitAF (wild-type) to Trp did not change the catalytic efficiency toward phenylacetonitrile, an arylacetonitrile. The mutants with nonpolar aliphatic amino acids (Ala, Gly, Leu, or Val) at location 140 had lower activity, and those with charged amino acids (Asp, Glu, or Arg) exhibited nearly no activity for phenylacetonitrile. Molecular modeling showed that the hydrophobic benzene ring at position 140 supports a mechanism in which the thiol group of Cys-163 carries out a nucleophilic attack on a cyanocarbon of the substrate. Characterization of the role of the Phe-140 residue demonstrated the molecular determinant for the efficient formation of arylcarboxylic acids.

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17

Suzuki, H., M. Ohishi, M. Morimoto, N. Kaifu, P. Friberg, W. M. Irvine, H. E. Matthews, and S. Saito. "Recent Observations of Organic Molecules in Nearby Cold, Dark Interstellar Clouds." Symposium - International Astronomical Union 112 (1985): 139–44. http://dx.doi.org/10.1017/s0074180900146443.

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We report recent investigations of the organic chemistry of relatively nearby cold, dark interstellar clouds. Specifically, we confirm the presence of interstellar tricarbon monoxide (C3O) in Taurus Molecular Cloud1 (TMC-1); report the first detection in such regions of acetaldehyde (CH3CHO), the most complex oxygen-containing organic molecule yet found in dark clouds; report the first astronomical detection of several molecular rotational transitions, including the J=18−17 and 14−13 transitions of cyanodiacetylene (HC5N), the 101−000 transition of acetaldehyde, and the J=5−4 transition of C3O; and set a significant upper limit on the abundance of cyanocarbene (HCCN) as a result of the first reported interstellar search for this molecule.

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18

Bonamico, Mario, Vincenzo Fares, Alberto Flamini, Anna M. Giuliani, and Patrizia Imperatori. "Electronic and structural properties of novel cyanocarbon dyes based on tetracyanoethylene." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1988): 1447. http://dx.doi.org/10.1039/p29880001447.

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19

YU, H., G. SRDANOV, K. HASHARONI, and F. WUDL. "ChemInform Abstract: Decacyanooctatetraene Dianion: A Model System for Cyanocarbon-Based Conjugated Polymers." ChemInform 29, no. 7 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199807069.

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20

Hyatt, I. F. Dempsey, and Mitchell P. Croatt. "Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes." Angewandte Chemie 124, no. 30 (June 22, 2012): 7629–32. http://dx.doi.org/10.1002/ange.201203062.

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21

Hyatt, I. F. Dempsey, and Mitchell P. Croatt. "Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes." Angewandte Chemie International Edition 51, no. 30 (June 22, 2012): 7511–14. http://dx.doi.org/10.1002/anie.201203062.

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22

Banert, Klaus, Manfred Hagedorn, Jens Wutke, Petra Ecorchard, Dieter Schaarschmidt, and Heinrich Lang. "Elusive ethynyl azides: trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes." Chemical Communications 46, no. 23 (2010): 4058. http://dx.doi.org/10.1039/c0cc00079e.

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23

Kaul, Bharat B., and Gordon T. Yee. "A charge-transfer salt magnet based on a non-cyanocarbon acceptor, 1,4,9,10-anthracenetetrone and decamethylferrocene." Polyhedron 20, no. 11-14 (May 2001): 1757–59. http://dx.doi.org/10.1016/s0277-5387(01)00685-4.

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24

Soleimani, Ebrahim, Mohammad Mehdi Khodaei, and Afsaneh Taheri Kal Koshvandi. "One-pot three-component reaction: Synthesis of substituted β-cyanocarbonyls in aqueous media." Comptes Rendus Chimie 15, no. 4 (April 2012): 273–77. http://dx.doi.org/10.1016/j.crci.2012.01.004.

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25

MAIER, G., H. P. REISENAUER, and K. RADEMACHER. "ChemInform Abstract: Heterocumulenes. Part 11. Cyanocarbene, Isocyanocarbene, and Azacyclopropenylidene: A Matrix-Spectroscopic Study." ChemInform 30, no. 5 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199905032.

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26

Bruce, Michael I., Mark A. Buntine, Karine Costuas, Benjamin G. Ellis, Jean-François Halet, Paul J. Low, Brian W. Skelton, and Allan H. White. "Some ruthenium complexes containing cyanocarbon ligands: syntheses, structures and extent of electronic communication in binuclear systems." Journal of Organometallic Chemistry 689, no. 21 (October 2004): 3308–26. http://dx.doi.org/10.1016/j.jorganchem.2004.07.030.

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27

Zhao, Zeng-Xia, Hong-Xing Zhang, and Chia-Chung Sun. "Theoretical Studies on Low-Lying Electronic States of Cyanocarbene HCCN and Its Ionic States." Journal of Physical Chemistry A 112, no. 47 (November 27, 2008): 12125–31. http://dx.doi.org/10.1021/jp8070663.

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28

Banert, Klaus, Manfred Hagedorn, Jens Wutke, Petra Ecorchard, Dieter Schaarschmidt, and Heinrich Lang. "ChemInform Abstract: Elusive Ethynyl Azides: Trapping by 1,3-Dipolar Cycloaddition and Decomposition to Cyanocarbenes." ChemInform 41, no. 43 (September 30, 2010): no. http://dx.doi.org/10.1002/chin.201043031.

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29

Koput, Jacek. "Ab Initio Heat of Formation and Singlet−Triplet Splitting for Cyanocarbene (HCCN) and Isocyanocarbene (HCNC)." Journal of Physical Chemistry A 107, no. 23 (June 2003): 4717–23. http://dx.doi.org/10.1021/jp027774h.

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30

Chen, Chien-Hong, Yung-Su Chang, Chien-Yeh Yang, Tai-Nan Chen, Chien-Ming Lee, and Wen-Feng Liaw. "Preparative and structural studies on iron(ii)–thiolate cyanocarbonyls: relevance to the [NiFe]/[Fe]-hydrogenases." Dalton Trans., no. 1 (2004): 137–43. http://dx.doi.org/10.1039/b311059a.

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31

Oturan, Mehmet Ali, Jean Pinson, Jean-Michel Saveant, and André Thiebault. "Electrochemically induced SRN1 aromatic nucleophilic substitution. Monoanions of β-dicarbonyl and β-cyanocarbonyl compounds as nucleophiles." Tetrahedron Letters 30, no. 11 (January 1989): 1373–76. http://dx.doi.org/10.1016/s0040-4039(00)99468-1.

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32

Goldberg, Norman, Andreas Fiedler, and Helmut Schwarz. "Cyanocarbene HCCN, Isocyanocarbene HCNC, Iminovinylidene HNCC, and Their Ionic Counterparts: A Combined Experimental and Theoretical Study." Journal of Physical Chemistry 99, no. 42 (October 1995): 15327–34. http://dx.doi.org/10.1021/j100042a002.

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33

Chiou, Tzung-Wen, and Wen-Feng Liaw. "Nickel–thiolate and iron–thiolate cyanocarbonyl complexes: Modeling the nickel and iron sites of [NiFe] hydrogenase." Comptes Rendus Chimie 11, no. 8 (August 2008): 818–33. http://dx.doi.org/10.1016/j.crci.2008.04.003.

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34

Herndon, James, Binay Ghorai, Shaofeng Duan, and Delu Jiang. "Coupling of β-Cyanocarbene-Chromium Complexes with 2-Alkynylbenzoyl Derivatives: A [5+5]-Cycloaddition Approach to Phenanthridines." Synthesis 2006, no. 21 (November 2006): 3661–69. http://dx.doi.org/10.1055/s-2006-950286.

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35

Liaw, Weng-Feng, Chien-Ming Lee, I. Jui Hsu, Shyue-Chu Ke, Gene-Hsiang Lee, and Yu Wang. "Ni-thiolate and Fe-thiolate-cyanocarbonyl complexes modeling the nickel/iron site and reactivity of [NiFe] hydrogenases." Journal of Inorganic Biochemistry 96, no. 1 (July 2003): 56. http://dx.doi.org/10.1016/s0162-0134(03)80500-7.

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36

Yoshida, Hiroto, Masahiko Watanabe, Joji Ohshita, and Atsutaka Kunai. "Aryne insertion into α-cyanocarbonyl compounds: direct introduction of carbonyl and cyanomethyl moieties into the aromatic skeletons." Tetrahedron Letters 46, no. 39 (September 2005): 6729–31. http://dx.doi.org/10.1016/j.tetlet.2005.07.119.

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37

Hojatti, M., A. J. Kresge, and W. H. Wang. "Cyanocarbon acids. Direct evidence that their ionization is not an encounter-controlled process and rationalization of the unusual solvent isotope effects." Journal of the American Chemical Society 109, no. 13 (June 1987): 4023–28. http://dx.doi.org/10.1021/ja00247a031.

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38

Buschmann, Wayne E., Atta M. Arif, and Joel S. Miller. "Isolation and structural determination of {(1,1,2,2-tetracyano-1,2-ethanediyl)bis[imino(cyanomethylene)]}bis(cyanamide) ion(2–), [C12N12]2–, a new cyanocarbon." J. Chem. Soc., Chem. Commun., no. 22 (1995): 2343–44. http://dx.doi.org/10.1039/c39950002343.

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39

Bruce, Michael I., Brian W. Skelton, Allan H. White, and Natasha N. Zaitseva. "Reactions of Ru(CCPh)(PPh3)2Cp* with tetracyanoethene: cycloaddition, formation of unusual η2-CNR complexes and oligomerisation via bridging cyanocarbon ligands." Journal of the Chemical Society, Dalton Transactions, no. 24 (November 13, 2001): 3627–33. http://dx.doi.org/10.1039/b105131h.

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40

Liaw, Wen-Feng, Wen-Ting Tsai, Hung-Bin Gau, Chien-Ming Lee, Shin-Yuan Chou, Wen-Yuan Chen, and Gene-Hsiang Lee. "Dinuclear Iron(II)−Cyanocarbonyl Complexes Linked by Two/Three Bridging Ethylthiolates: Relevance to the Active Site of [Fe] Hydrogenases." Inorganic Chemistry 42, no. 8 (April 2003): 2783–88. http://dx.doi.org/10.1021/ic0261225.

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41

Felten, Christian, Jens Richter, Wolfgang Priebsch, and Dieter Rehder. "Heptakoordinierte Halogeno- und Cyanocarbonyl-Komplexe des Niob(I): Darstellung und spektroskopische Charakterisierung. Röntgenstruktur voncis-[ClNb(CO)2(Ph2PCH2CH2PPh2)2]." Chemische Berichte 122, no. 9 (September 1989): 1617–22. http://dx.doi.org/10.1002/cber.19891220904.

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42

Kalcher, Josef. "Singlet–triplet splittings and electron affinities of selected cyanocarbenes, XCCN (X=H, F, Cl, C2H, CN): carbenes with a stable excited negative ion state." Chemical Physics Letters 403, no. 1-3 (February 2005): 146–51. http://dx.doi.org/10.1016/j.cplett.2005.01.007.

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43

Etienne, Michel, and Jacques E. Guerchais. "Transition metal–cyanocarbon chemistry. Part 8. Cyano-substituted buta-1,3- dienylidene bridged di-iron complexes from unprecedented cyanoalkyne insertion into the carbon–hydrogen bond of a bridging alkenylidene ligand." J. Chem. Soc., Dalton Trans., no. 11 (1989): 2187–92. http://dx.doi.org/10.1039/dt9890002187.

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44

Hyatt, I. F. Dempsey, Mitchell P. Croatt, Klaus Banert, René Arnold, Manfred Hagedorn, Philipp Thoss, and Alexander A. Auer. "Titelbild: Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes / 1-Azido-1-Alkynes: Synthesis and Spectroscopic Characterization of Azidoacetylene (Angew. Chem. 30/2012)." Angewandte Chemie 124, no. 30 (July 16, 2012): 7449. http://dx.doi.org/10.1002/ange.201204825.

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45

Chen, Chien-Hong, Li-Chun Wang, and Wen-Feng Liaw. "Preparative and Structural Studies on Ruthenium(II)-Thiolate Cyanocarbonyls: Comparison to the [Fe(CO)x(CN)y(SR)z]n−Coordination Modes of Active Sites of Hydrogenases." Journal of the Chinese Chemical Society 51, no. 5B (October 2004): 1121–26. http://dx.doi.org/10.1002/jccs.200400166.

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46

Kergoat, R., L. C. Gomes de Lima, C. Jégat, N. Le Berre, M. M. Kubicki, J. E. Guerchais, and P. L'Haridon. "Transition metal-cyanocarbon chemistry X. Reactions of monocyanoacetylene and dicyanoacetylene with organometallic compounds of cobalt(I) and nickel(II). Crystal structure of [Co(CCCN)2(η5-C5H5)(P(C6H5)3)]." Journal of Organometallic Chemistry 389, no. 1 (June 1990): 71–84. http://dx.doi.org/10.1016/0022-328x(90)85394-e.

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47

Hyatt, I. F. Dempsey, Mitchell P. Croatt, Klaus Banert, René Arnold, Manfred Hagedorn, Philipp Thoss, and Alexander A. Auer. "Cover Picture: Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes / 1-Azido-1-Alkynes: Synthesis and Spectroscopic Characterization of Azidoacetylene (Angew. Chem. Int. Ed. 30/2012)." Angewandte Chemie International Edition 51, no. 30 (July 16, 2012): 7335. http://dx.doi.org/10.1002/anie.201204825.

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48

Kubicki, Marek M., Rene Kergoat, Luiz C. Gomes De Lima, Monique Cariou, Henri Scordia, Jacques E. Guerchais, and Paul L'Haridon. "Transition metalcyanocarbon chemistry. Part V. Crystal and molecular structure of biscyclopentadienyl complexes containing a σ-cyanoalkyl and a σ-cyanoalkenyl ligand: (η5-C5H5)2Mo[S(C6H5)](σ-CH(CN)CH3) and (η5-C5H5)2Mo(S2CN(C2H5)2)(σ-C(CN)CH2)." Inorganica Chimica Acta 104, no. 3 (November 1985): 191–96. http://dx.doi.org/10.1016/s0020-1693(00)86770-5.

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49

Cariou, Monique, Marek M. Kubicki, Rene Kergoat, Luiz C. Gomes De Lima, Henri Scordia, and Jacques E. Guerchais. "Transition metalcyanocarbon chemistry. Part IV. Reactions of bent biscyclopentadienyl complexes of molybdenum and tungsten of the type (η5-C5H5)2MH(σ-CRCHR′) (M = Mo, W; R = CN; R′ = H; M = Mo; R = CN, CF3; R′ = H; R = R′ = CN) and (η5-C5H5)2Mo(σ-C(CN)CH2) ((Z)-CHCHCN) with HX (X = Cl, O2CCF3, SPh, SMe, SH) reagents. Protonation of σ-alkenyl ligands." Inorganica Chimica Acta 104, no. 3 (November 1985): 185–90. http://dx.doi.org/10.1016/s0020-1693(00)86769-9.

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50

HERTLER, W. R., W. MAHLER, L. R. MELBY, J. S. MILLER, R. E. PUTSCHER, and O. W. WEBSTER. "ChemInform Abstract: Cyanocarbons - Their History from Conducting to Magnetic Organic Charge Transfer Salts." ChemInform 21, no. 13 (March 27, 1990). http://dx.doi.org/10.1002/chin.199013336.

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