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N-Salicylidene aniline derivatives based on the N′-thiophosphorylated thiourea scaffold

Bibliographic reference Safin, D. A. ; Babashkina, M. G. ; Robeyns, Koen ; Bolte, M. ; Garcia, Yann. N-Salicylidene aniline derivatives based on the N′-thiophosphorylated thiourea scaffold. In: CrystEngComm, Vol. 16, p. 7053-7061 (2014)
Permanent URL http://hdl.handle.net/2078.1/146347
  1. Moulton Brian, Zaworotko Michael J., From Molecules to Crystal Engineering:  Supramolecular Isomerism and Polymorphism in Network Solids, 10.1021/cr9900432
  2. Lehn Jean-Marie, Supramolecular Chemistry : Concepts and Perspectives, ISBN:9783527607433, 10.1002/3527607439
  3. Brunsveld L., Folmer B. J. B., Meijer E. W., Sijbesma R. P., Supramolecular Polymers, 10.1021/cr990125q
  4. G. A. Jeffery , An Introduction To Hydrogen Bonding , Oxford University Press , 1997
  5. Guthrie Frederick, XXVIII.—On the iodide of iodammonium, 10.1039/js8631600239
  6. Seamon, Chem. News, 44, 188 (1881)
  7. Benesi H. A., Hildebrand J. H., A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons, 10.1021/ja01176a030
  8. Hassel O., Structural Aspects of Interatomic Charge-Transfer Bonding, 10.1126/science.170.3957.497
  9. Metrangolo Pierangelo, Resnati Giuseppe, Halogen Bonding: A Paradigm in Supramolecular Chemistry, 10.1002/1521-3765(20010618)7:12<2511::aid-chem25110>3.0.co;2-t
  10. Metrangolo Pierangelo, Meyer Franck, Pilati Tullio, Resnati Giuseppe, Terraneo Giancarlo, Halogen Bonding in Supramolecular Chemistry, 10.1002/anie.200800128
  11. Beale Thomas M., Chudzinski Michael G., Sarwar Mohammed G., Taylor Mark S., Halogen bonding in solution: thermodynamics and applications, 10.1039/c2cs35213c
  12. M. D. Hollingsworth and K. D. M.Harris , Urea, Thiourea and Selenourea, in Comprehensive Supramolecular Chemistry , ed. J. L. Atwood , J. E. D. Davis , D. D. MacNicol and F. Vögtle , Pergamon, Oxford, UK , 1996 , p. 177
  13. Schmidtchen Franz P., Berger Michael, Artificial Organic Host Molecules for Anions, 10.1021/cr9603845
  14. Harris Kenneth D. M., Meldola Lecture: understanding the properties of urea and thiourea inclusion compounds, 10.1039/cs9972600279
  15. Beer Paul D., Gale Philip A., Anion Recognition and Sensing: The State of the Art and Future Perspectives, 10.1002/1521-3773(20010202)40:3<486::aid-anie486>3.0.co;2-p
  16. Choi Kihang, Hamilton Andrew D., Macrocyclic anion receptors based on directed hydrogen bonding interactions, 10.1016/s0010-8545(02)00305-3
  17. Custelcean Radu, Crystal engineering with urea and thiourea hydrogen-bonding groups, 10.1039/b708921j
  18. Steed Jonathan W., Anion-tuned supramolecular gels: a natural evolution from urea supramolecular chemistry, 10.1039/b926219a
  19. Hay Benjamin P., De novo structure-based design of anion receptors, 10.1039/c0cs00075b
  20. Li Ai-Fang, Wang Jin-He, Wang Fang, Jiang Yun-Bao, Anion complexation and sensing using modified urea and thiourea-based receptors, 10.1039/b926160p
  21. Gale Philip A., Anion receptor chemistry: highlights from 2008 and 2009, 10.1039/c001871f
  22. Amendola Valeria, Fabbrizzi Luigi, Mosca Lorenzo, Anion recognition by hydrogen bonding: urea-based receptors, 10.1039/b822552b
  23. Dydio Paweł, Lichosyt Dawid, Jurczak Janusz, Amide- and urea-functionalized pyrroles and benzopyrroles as synthetic, neutral anion receptors, 10.1039/c1cs15006e
  24. Sokolov F., Brusko V., Zabirov N., Cherkasov R., N-Acylamidophosphinates: Structure, Properties and Complexation Towards Main Group Metal Cations, 10.2174/138527206775193031
  25. Sokolov Felix D., Safin Damir A., Babashkina Maria G., Zabirov Nail G., Brusko Vasiliy V., Mironov Nikolay A., Krivolapov Dmitry B., Litvinov Igor A., Cherkasov Rafael A., Solomonov Boris N., A “sodium trap” based on benzo-15-crown-5 with an exocyclic N-(thiophosphoryl)thiourea moiety, 10.1016/j.poly.2006.12.024
  26. F. D. Sokolov , V. V.Brusko , D. A.Safin , R. A.Cherkasov and N. G.Zabirov , Coordination Diversity of N-Phosphorylated Amides and Ureas Towards VIIIB Group Cations , in Transition Metal Chemistry: New Research , ed. B. Varga and L. Kis , Nova Science Publishers Inc. , Hauppauge NY, USA , 2008 , p. 101
  27. Luckay R. C., Sheng X., Strasser C. E., Raubenheimer H. G., Safin D. A., Babashkina M. G., Klein A., Competitive bulk liquid membrane transport of some metal ions using RC(S)NHP(S)(OiPr)2 as ionophores. Unusual supramolecular “honeycomb” aggregate of the polynuclear copper(I) complex of H2NC(S)NHP(S)(OiPr)2, 10.1039/b904114a
  28. Luckay Robert C., Sheng Xia, Strasser Christoph E., Raubenheimer Helgard G., Safin Damir A., Babashkina Maria G., Klein Axel, Competitive bulk liquid membrane transport and solvent extraction of some metal ions using RC(S)NHP(X)(OiPr)2 (X = O, S) as ionophores. Formation of the polynuclear complex of [Ag(NC–NP(S)(OiPr)2)]n, 10.1039/b910650b
  29. Babashkina Maria G., Safin Damir A., Bolte Michael, Srebro Monika, Mitoraj Mariusz, Uthe André, Klein Axel, Köckerling Martin, Intramolecular hydrogen bonding controls 1,3-N,S- vs. 1,5-S,S′-coordination in NiII complexes of N-thiophosphorylated thioureas RNHC(S)NHP(S)(OiPr)2, 10.1039/c0dt01382j
  30. Babashkina Maria G., Safin Damir A., Bolte Michael, Garcia Yann, N-(Diisopropylthiophosphoryl)-N′-(R)-thioureas: synthesis, characterization, crystal structures and competitive bulk liquid membrane transport of some metal ions, 10.1039/c2dt11862a
  31. Sokolov Felix D., Safin Damir A., Zabirov Nail G., Yamalieva Luiza N., Krivolapov Dmitry B., Litvinov Igor A., Reaction of N-diisopropoxyphosphorylthiobenzamide (HL) with the CoII cation: the crystal structure of CoL2 and CoL2·2HL complexes, 10.1070/mc2004v014n02abeh001874
  32. Safin Damir A., Sokolov Felix D., Zabirov Nail G., Brusko Vasiliy V., Krivolapov Dmitry B., Litvinov Igor A., Luckay Robert C., Cherkasov Rafael A., Studies on cobalt(II) complexes with N-thioacylamido(thio)phosphates: X-ray crystal structure of the Co[PhC(S)NP(S)(OPri)2]2, 10.1016/j.poly.2006.06.005
  33. Sokolov Felix D., Safin Damir A., Zabirov Nail G., Brusko Vasiliy V., Khairutdinov Bulat I., Krivolapov Dmitry B., Litvinov Igor A., Coordination Mode of the Zinc(II) and Cadmium(II) Cations withN-(Diisopropoxyphosphoryl)thiobenzamide, 10.1002/ejic.200501005
  34. Safin Damir A., Sokolov Felix D., Szyrwiel Łukasz, Babashkina Maria G., Gimadiev Timur R., Hahn F. Ekkehardt, Kozlowski Henryk, Krivolapov Dmitriy B., Litvinov Igor A., Nickel(II) complexes with N-(thio)phosphorylthioureas AdNHC(S)NHP(X)(OiPr)2: Versatile coordination of phosphoryl (X=O) and thiophosphoryl (X=S) derivatives, 10.1016/j.poly.2008.04.014
  35. Babashkina Maria G., Safin Damir A., Bolte Michael, Klein Axel, Intramolecular hydrogen bond controlled coordination of N-thiophosphorylated thiourea 2,6-Me2C6H3NHC(S)NHP(S)(OiPr)2 with Ni(II), 10.1016/j.inoche.2009.05.030
  36. Safin Damir A., Klein Axel, Babashkina Maria G., Nöth Heinrich, Krivolapov Dmitriy B., Litvinov Igor A., Kozlowski Henryk, Versatile coordination of N-(diisopropoxyphosphoryl)-p-bromothiobenzamide towards Zn(II) and Cd(II), 10.1016/j.poly.2009.03.007
  37. Safin Damir A., Babashkina Maria G., Bolte Michael, Hahn F. Ekkehardt, Highly efficient [Ni{iPrHNC(S)NP(S)(OiPr)2-1,3-N,S′}2]/PR3 (R3 = Me3, Me2Ph) complexes for the generation of Ni0 for catalysis, 10.1039/c1dt10056d
  38. Babashkina Maria G., Safin Damir A., Garcia Yann, Influence of the coordination mode in [Ni{RC(S)NP(S)(OiPr)2}2] for the formation of nickel-containing nanoparticles, 10.1039/c1dt11755f
  39. Babashkina Maria G., Safin Damir A., Srebro Monika, Kubisiak Piotr, Mitoraj Mariusz P., Bolte Michael, Garcia Yann, Influence of CH2Cl2for the structure stabilization of the NiIIcomplex [Ni{6-MeO(O)CC6H4NHC(S)NP(S)(OiPr)2-1,5-S,S′}2]·CH2Cl2, 10.1039/c1ce06322g
  40. Babashkina Maria G., Safin Damir A., Srebro Monika, Kubisiak Piotr, Mitoraj Mariusz P., Bolte Michael, Garcia Yann, Crucial Influence of the Intramolecular Hydrogen Bond on the Coordination Mode of RC(S)NHP(S)(OiPr)2in Homoleptic Complexes with NiII, 10.1002/ejic.201200890
  41. Safin Damir A., Babashkina Maria G., Garcia Yann, First paramagnetic PdIIcomplex with a PdN4S2coordination core, 10.1039/c2dt32505e
  42. Safin Damir A., Babashkina Maria G., Kubisiak Piotr, Mitoraj Mariusz P., Robeyns Koen, Goovaerts Etienne, Garcia Yann, Complexation properties of N-thiophosphorylated thiourea 2-PyNHC(S)NHP(S)(OiPr)2 towards NiII, 10.1039/c3dt32886d
  43. Safin Damir A., Babashkina Maria G., Robeyns Koen, Mitoraj Mariusz P., Kubisiak Piotr, Brela Mateusz, Garcia Yann, Experimental and theoretical investigations of the NiII complex with N-phosphorylated thiourea iPrNHC(S)NHP(O)(OPh)2, 10.1039/c3ce41195h
  44. J. C. Crano and R. J.Guglielmetti , Organic Photochromic and Thermochromic compounds , Plenum , New York , 1998
  45. Hadjoudis, Chem. Soc. Rev., 33, 579 (2004)
  46. Hadjoudis Eugene, Chatziefthimiou Spyros, Mavridis Irene, Anils: Photochromism by H-transfer, 10.2174/138527209787314797
  47. Haneda Tsuyoshi, Kawano Masaki, Kojima Takahiro, Fujita Makoto, Thermo-to-Photo-Switching of the Chromic Behavior of Salicylideneanilines by Inclusion in a Porous Coordination Network, 10.1002/anie.200700999
  48. Chatziefthimiou Spyros D., Lazarou Yannis G., Hadjoudis Eugene, Dziembowska Tereza, Mavridis Irene M., Keto Forms of Salicylaldehyde Schiff Bases:  Structural and Theoretical Aspects, 10.1021/jp064110p
  49. Robert François, Naik Anil D., Tinant Bernard, Robiette Raphaël, Garcia Yann, Insights into the Origin of Solid-State Photochromism and Thermochromism ofN-Salicylideneanils: The Intriguing Case of Aminopyridines, 10.1002/chem.200801932
  50. Robert François, Jacquemin Pierre-Loïc, Tinant Bernard, Garcia Yann, Trans-keto* form detection in non photochromic N-salicylidene aminomethylpyridines, 10.1039/c2ce00006g
  51. Robert François, Naik Anil D., Hidara Florence, Tinant Bernard, Robiette Raphaël, Wouters Johan, Garcia Yann, Engineering Solid-State Molecular Switches:N-Salicylidene N-Heterocycle Derivatives, 10.1002/ejoc.200901175
  52. Garcia Yann, Robert François, Naik Anil D., Zhou Guangyuan, Tinant Bernard, Robeyns Koen, Michotte Sébastien, Piraux Luc, Spin Transition Charted in a Fluorophore-Tagged Thermochromic Dinuclear Iron(II) Complex, 10.1021/ja205974q
  53. Safin Damir A., Robeyns Koen, Garcia Yann, Crown ether-containing N-salicylidene aniline derivatives: synthesis, characterization and optical properties, 10.1039/c2ce25600b
  54. Safin Damir A., Robeyns Koen, Garcia Yann, Solid-state thermo- and photochromism in N,N′-bis(5-X-salicylidene)diamines (X = H, Br), 10.1039/c2ra21631k
  55. Safin Damir A., Garcia Yann, First evidence of thermo- and two-step photochromism of tris-anils, 10.1039/c3ra40705e
  56. Robert, J. Phys.: Conf. Ser., 217, 012031 (2010)
  57. Robert, Möss. Eff. Ref. Data J., 34, 200 (2011)
  58. Robert François, Naik Anil D., Tinant Bernard, Garcia Yann, N-Salicylidene anil anions as thermo-sensitive components of organic–inorganic hybrid materials, 10.1016/j.ica.2011.08.040
  59. Jacquemin Pierre-Loïc, Robeyns Koen, Devillers Michel, Garcia Yann, Reversible photochromism of an N-salicylidene aniline anion, 10.1039/c3cc45080e
  60. Jacquemin Pierre-Loïc, Garcia Yann, Devillers Michel, Blends made from N-salicylidene aniline sulfonate derivatives and a polyampholyte matrix: in situ synthesis vs. solution mixing, 10.1039/c3tc31979b
  61. Safin Damir A., Bolte Michael, Garcia Yann, Photoreversible solid state negative photochromism of N-(3,5-dichlorosalicylidene)-1-aminopyrene, 10.1039/c4ce00589a
  62. Safin Damir A., Babashkina Maria G., Robeyns Koen, Rouzières Mathieu, Clérac Rodolphe, Garcia Yann, From a mononuclear NiII precursor to antiferromagnetically coupled trinuclear double-stranded helicates, 10.1039/c3dt52387j
  63. Baranov S. V., Sokolov F. D., Khairutdinov B. I., Zabirov N. G., Cherkasov R. A., Synthesis and structure of N-thiophosphorylthiourea containing 2,6-diaminopyridine fragment, 10.1134/s1070363207030255
  64. Safin Damir A., Babashkina Maria G., Bolte Michael, Sokolov Felix D., Brusko Vasiliy V., Complexes of N-thiophosphorylthioureas RNHC(S)NHP(S)(OiPr)2 (HL) (R=pyridin-2-yl, pyridin-3-yl, 6-amino-pyridin-2-yl) with copper(I): Crystal structures of Cu(PPh3)nL (n=1, 2), 10.1016/j.ica.2008.09.002
  65. Karatayeva F. Kh., Aganov A. V., Klochkov V. V., Dynamic1H,13C,31P NMR spectroscopy of the crown containing N-(thio)phosphoryl(thio)urea, 10.1007/bf03161861
  66. Karataeva, Russ. J. Gen. Chem., 70, 403 (2000)
  67. Karataeva, Russ. J. Gen. Chem., 70, 1062 (2000)
  68. Karataeva F. Kh., Yul’metov A. R., Zabirov N. G., Aganov A. V., Klochkov V. V., Structure and Intramolecular Lability of N-(Thio)phosphoryl(thio)amides: XIII. Structure of N-Phenyl-N′-(diisopropoxythiphosphoryl)thiourea, 10.1007/s11176-005-0333-8
  69. Angyl S. J., Angyal C. L., 268. The tautomerism of N-hetero-aromatic amines. Part I, 10.1039/jr9520001461
  70. Jaffé H. H., Doak G. O., The Basicities of Substituted Pyridines and their 1-Oxides, 10.1021/ja01622a001
  71. Albert Adrien, Phillips J. N., 264. Ionization constants of heterocyclic substances. Part II. Hydroxy-derivatives of nitrogenous six-membered ring-compounds, 10.1039/jr9560001294
  72. Jones R. A., Katritzky A. R., 262. Potentially tautomeric pyridines. Part II. 2-, 3-, and 4-Acetamido- and -benzamido-pyridine, 10.1039/jr9590001317
  73. Linnell Robert, Notes- Dissociation Constants of 2-Substituted Pyridines, 10.1021/jo01072a623
  74. Clarke, J. Chem. Soc., 1960 (1885)
  75. Bryson, J. Am. Chem. Soc., 82, 4558 (1960)
  76. Bryson A., The Effects of Substituents on the pKaValues and N-H Stretching Frequencies of 1- and 2-Naphthylamines, 10.1021/ja01503a029
  77. Bryson A., The Ionization Constants of 3-Substituted Pyridines, 3-Substituted Quinolines and 4-Substituted Isoquinolines, 10.1021/ja01503a030
  78. Safin Damir A., Bolte Michael, Shakirova Elmira R., Babashkina Maria G., The influence of the substituent [PhNHNH– and EtN(NH2)–] on the N-thiophosphorylated thiosemicarbazides RC(S)NHP(S)(OiPr)2 crystal design, 10.1016/j.poly.2008.11.060
  79. Babashkina Maria G., Safin Damir A., Bolte Michael, Klein Axel, Synthesis of N-(thio)phosphorylated thiosemicarbazides RC(S)NHP(X)(OiPr)2 (X=S, R=NH2N(Me)–; X=O, R=NH2N(Me)–, PhNHNH–): Reaction of NH2N(Me)C(S)NHP(S)(OiPr)2 with acetone, 10.1016/j.poly.2009.05.042
  80. Safin Damir A., Babashkina Maria G., Bolte Michael, Klein Axel, Synthesis, characterization and complexation properties of N-phosphorylated thioureas RNHC(S)NHP(O)(OiPr)2 (R=2-Py, 3-Py) towards Ni(II), 10.1016/j.ica.2010.02.029
  81. Metrangolo Pierangelo, Neukirch Hannes, Pilati Tullio, Resnati Giuseppe, Halogen Bonding Based Recognition Processes:  A World Parallel to Hydrogen Bonding†, 10.1021/ar0400995
  82. Harada Jun, Fujiwara Toshikatsu, Ogawa Keiichiro, Crucial Role of Fluorescence in the Solid-State Thermochromism of Salicylideneanilines, 10.1021/ja076635g
  83. Hadjoudis E., Verganelakis V., Trapalis C., Kordas G., 10.1023/a:1008310718276
  84. Zhang Lei Z., Xiong Ying, Cheng Peng, Tang Guo-Qing, Liao Dai-Zheng, Molecular orbital confinement of a Schiff base molecule in the nanoporous channels of MCM-41 host, 10.1016/s0009-2614(02)00606-1
  85. Sakagami S., Koga T., Takase A., Liquid Crystalline Properties and Photochromism of 4-Halogeno-N-(4-alkoxysalicylidene) anilines, 10.1080/10587250210540
  86. Amimoto Kiichi, Kawato Toshio, Photochromism of organic compounds in the crystal state, 10.1016/j.jphotochemrev.2005.12.002
  87. Ziółek Marcin, Sobczak Izabela, Photochromism and hydrolysis of aromatic Schiff base N,N′-bis(salicylidene)-p-phenylenediamine (BSP) studied in heterogeneous environments, 10.1007/s10847-008-9509-2
  88. Oxford diffraction data collection and data reduction, Version 171.34.40
  89. Sheldrick George M., A short history ofSHELX, 10.1107/s0108767307043930
  90. Spek Anthony L., Structure validation in chemical crystallography, 10.1107/s090744490804362x
  91. Bruno Ian J., Cole Jason C., Edgington Paul R., Kessler Magnus, Macrae Clare F., McCabe Patrick, Pearson Jonathan, Taylor Robin, New software for searching the Cambridge Structural Database and visualizing crystal structures, 10.1107/s0108768102003324