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Articles

Synthesis, characterization, crystal structure, Hirshfeld surface analysis, and theoretical study on a N-heterocyclic carbene salt and two NHC–palladium complexes

, , , & ORCID Icon
Pages 493-504 | Received 18 Aug 2020, Accepted 01 Dec 2020, Published online: 10 Mar 2021

References

  • Carlsson, E.; Lindberg, P.; von Unge, S. Two of a Kind. Chem. Br. 2002, 38, 42–45.
  • Berneth, H. Methine Dyes and Pigments. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2008. DOI: 10.1002/14356007.a16_487.pub2.
  • Nolan, S. P., Ed. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, 2006.
  • Glorius, F., Ed. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer-Verlag: Berlin, 2007.
  • Kascatan-Nebioglu, A.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. N-Heterocyclic Carbene-Silver Complexes: A New Class of Antibiotics. Coord. Chem. Rev. 2007, 251, 884–895. DOI: 10.1016/j.ccr.2006.08.019.
  • Kushwaha, N.; Kaushik, D. Recent Advances and Future Prospects of Phthalimide Derivatives. J. Appl. Pharm. Sci. 2016, 6, 159–171. DOI: 10.7324/JAPS.2016.60330.
  • Imran, M.; Bisht, A. S.; Asif, M. A Review on Biological and Chemical Potential of Phthalimide and Maleimide Derivatives. Acta Scientific Pharm. Sci. 2019, 3, 51–67.
  • Karthik, C. S.; Mallesha, L.; Mallu, P. Investigation of Antioxidant Properties of Phthalimide Derivatives. Canadian Chem. Trans. 2015, 3, 199–206. DOI: 10.13179/canchemtrans.2015.03.02.0194.
  • Fortman, G. C.; Nolan, S. P. N-Heterocyclic Carbene (NHC) Ligands and Palladium in Homogeneous Cross-Coupling Catalysis: A Perfect Union. Chem. Soc. Rev. 2011, 40, 5151–5169. DOI: 10.1039/C1CS15088J.
  • Shi, S.; Nolan, S. P.; Szostak, M. Well-Defined Palladium(II)-NHC Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective N-C/O-C Cleavage. Acc. Chem. Res. 2018, 51, 2589–2599. DOI: 10.1021/acs.accounts.8b00410.
  • Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions. J. Am. Chem. Soc. 2006, 128, 4101–4111. DOI: 10.1021/ja057704z.
  • Kantchev, E. A. B.; Ying, J. Y. Practical One-Pot, Three-Component Synthesis of N-Heterocyclic Carbene (NHC) Ligated Palladacycles Derived from N,N-Dimethylbenzylamine. Organometallics 2009, 28, 289–299. DOI: 10.1021/om8008475.
  • Navarro, O.; Kelly, R. A.; Nolan, S. P. A General Method for the Suzuki-Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-Ortho-Substituted Biaryls in 2-Propanol at Room Temperature. J. Am. Chem. Soc. 2003, 125, 16194–16195. DOI: .
  • Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A.; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Synthetic and Structural Studies of (NHC)Pd(Allyl)Cl Complexes (NHC = N-Heterocyclic Carbene). Organometallics 2004, 23, 1629–1635. DOI: 10.1021/om034319e.
  • Chartoire, A.; Lesieur, M.; Falivene, L.; Slawin, A. M. Z.; Cavallo, L.; Cazin, C. S. J.; Nolan, S. P. [Pd(IPr*)(Cinnamyl)Cl]: An Efficient Pre-Catalyst for the Preparation of Tetra-Ortho-Substituted Biaryls by Suzuki-Miyaura Cross-Coupling. Chemistry 2012, 18, 4517–4521. DOI: 10.1002/chem.201104009.
  • O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Easily Prepared Air- and Moisture-Stable Pd-NHC (NHC = N-Heterocyclic Carbene) Complexes: A Reliable, User-Friendly, Highly Active Palladium Precatalyst for the Suzuki-Miyaura Reaction. Chemistry 2006, 12, 4743–4748. DOI: 10.1002/chem.200600251.
  • Marion, N.; Nolan, S. P. Well-Defined N-Heterocyclic Carbenes-Palladium(II) Precatalysts for Cross-Coupling Reactions. Acc. Chem. Res. 2008, 41, 1440–1449. DOI: 10.1021/ar800020y.
  • Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. The Development of Bulky Palladium NHC Complexes for the Most-Challenging Cross-Coupling Reactions. Angew. Chem. Int. Ed. Engl. 2012, 51, 3314–3332. DOI: 10.1002/anie.201106131.
  • Arslan, H.; Özdemir, İ.; Vanderveer, D.; Demir, S.; Çetinkaya, B. Synthesis and Characterization of N-Heterocyclic Carbene Palladium Complex and Its Application on Direct Arylation of Benzoxazoles and Benzothiazoles with Aryl Bromides. J. Coord. Chem. 2009, 62, 2591–2599. DOI: 10.1080/00958970902923313.
  • Çekirdek, S.; Yaşar, S.; Özdemir, İ. Palladium(II)‐N‐Heterocyclic Carbene Complexes: Synthesis, Characterization and Catalytic Application. Appl. Organometal. Chem. 2014, 28, 423–431. DOI: 10.1002/aoc.3143.
  • Kaloğlu, M.; Özdemir, İ. Palladium(II)‐N‐ Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides. Appl. Organometal. Chem. 2018, 32, e4399. DOI: 10.1002/aoc.4399.
  • Kaloğlu, M.; Kaloğlu, N.; Özdemir, İ. Direct C‐H Bond Arylation of C2‐Blocked Pyrrole with Aryl Halides Using Palladium(II)‐N‐Heterocyclic Carbene Catalysts. ChemistrySelect 2018, 3, 5600–5607. DOI: 10.1002/slct.201801045.
  • Kaloğlu, M.; Özdemir, İ. PEPPSI-Pd-NHC Catalyzed Suzuki-Miyaura Cross-Coupling Reactions in Aqueous Media. Tetrahedron 2019, 75, 2306–2313. DOI: 10.1016/j.tet.2019.02.062.
  • Kaloğlu, M.; Gürbüz, N.; Yıldırım, İ.; Özdemir, N.; Özdemir, İ. Well‐Defined PEPPSI‐Themed Palladium–NHC Complexes: Synthesis, and Catalytic Application in the Direct Arylation of Heteroarenes. Appl. Organometal. Chem. 2020, 34, e5387. DOI: 10.1002/aoc.5387.
  • Kaloğlu, M.; Özdemir, İ. The Direct C4-Arylation of 3,5-Dimethylisoxazole with Aryl Bromides Catalyzed by Imidazolidin-2-Ylidene Based palladium-PEPPSI Complexes. Inorg. Chim. Acta 2020, 504, 119454. DOI: 10.1016/j.ica.2020.119454.
  • X-AREA (Version 1.18) and X-RED32 (Version 1.04); Stoe & Cie: Darmstadt, Germany, 2002.
  • Burla, M. C.; Caliandro, R.; Carrozzini, B.; Cascarano, G. L.; Cuocci, C.; Giacovazzo, C.; Mallamo, M.; Mazzone, A.; Polidori, G. Crystal Structure Determination and Refinement via SIR2014. J. Appl. Crystallogr. 2015, 48, 306–309. DOI: 10.1107/S1600576715001132.
  • Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3–8. DOI: 10.1107/S2053229614024218.
  • Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341. DOI: 10.1107/S0021889808042726.
  • Dennington, R.; Keith, T.; Millam, J. GaussView. Version 5.0; Semichem Inc.: Shawnee Mission, KS, 2009.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; et al. Gaussion 09. Revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
  • Heyd, J.; Scuseria, G. E. Assessment and Validation of a Screened Coulomb Hybrid Density Functional. J. Chem. Phys. 2004, 120, 7274–7280. DOI: 10.1063/1.1668634.
  • Heyd, J.; Scuseria, G. E. Efficient Hybrid Density Functional Calculations in Solids: Assessment of the Heyd-Scuseria-Ernzerhof Screened Coulomb Hybrid Functional. J. Chem. Phys. 2004, 121, 1187–1192. DOI: 10.1063/1.1760074.
  • Heyd, J.; Peralta, J. E.; Scuseria, G. E.; Martin, R. L. Energy Band Gaps and Lattice Parameters Evaluated with the Heyd-Scuseria-Ernzerhof Screened Hybrid Functional. J. Chem. Phys. 2005, 123, 174101. DOI: 10.1063/1.2085170.
  • Küchle, W.; Dolg, M.; Stoll, H.; Preuss, H. Energy-Adjusted Pseudopotentials for the Actinides. Parameter Sets and Test Calculations for Thorium and Thorium Monoxide. J. Chem. Phys. 1994, 100, 7535–7542. DOI: 10.1063/1.466847.
  • Spackman, M. A.; McKinnon, J. J. Fingerprinting Intermolecular Interactions in Molecular Crystals. CrystEngComm 2002, 4, 378–392. DOI: 10.1039/B203191B.
  • Seth, S. K. Structural Characterization and Hirshfeld Surface Analysis of a CoII Complex with Imidazo[1,2-a]Pyridine. Acta Crystallogr. E Crystallogr. Commun. 2018, 74, 600–606. DOI: 10.1107/S2056989018003857.
  • Saini, Y.; Mahajan, S.; Kapoor, K. K.; Hundal, G.; Seth, S. K. Diverse Structural Assemblies of a Series of Ninhydrin Derivatives: Quantitative Analyses from Experimental and Theoretical Studies. J. Mol. Struct. 2021, 1224, 128920. DOI: 10.1016/j.molstruc.2020.128920.
  • Spackman, M. A.; Byrom, P. G. A Novel Definition of a Molecule in a Crystal. Chem. Phys. Lett. 1997, 267, 215–220. DOI: 10.1016/S0009-2614(97)00100-0.
  • McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Hirshfeld Surfaces: A New Tool for Visualising and Exploring Molecular Crystals. Chem. Eur. J. 1998, 4, 2136–2141. DOI: 10.1002/(SICI)1521-3765(19981102)4:11%3C2136::AID-CHEM2136%3E3.0.CO;2-G.
  • McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Towards Quantitative Analysis of Intermolecular Interactions with Hirshfeld Surfaces. Chem. Commun. 2007, 37, 3814–3816. DOI: 10.1039/B704980C.
  • Rohl, A. L.; Moret, M.; Kaminsky, W.; Claborn, K.; Mckinnon, J. J.; Kahr, B. Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone. Cryst. Growth Des. 2008, 8, 4517–4525. DOI: 10.1021/cg8005212.
  • Maity, T.; Mandal, H.; Bauza, A.; Samanta, B. C.; Frontera, A.; Seth, S. K. Quantifying Conventional C–H···π(Aryl) and Unconventional C–H···π(Chelate) Interactions in Dinuclear Cu(II) Complexes: Experimental Observations, Hirshfeld Surface and Theoretical DFT Study. New J. Chem. 2018, 42, 10202–10213. DOI: 10.1039/C8NJ00747K.
  • Seth, S. K. The Importance of CH···X (X = O, π) Interaction of a New Mixed Ligand Cu(II) Coordination Polymer: Structure, Hirshfeld Surface and Theoretical Studies. Crystals 2018, 8, 455. DOI: 10.3390/cryst8120455.
  • Turner, M. J.; MacKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. Crystal Explorer, Version 17.5; University of Western Avustralia: Pert, 2017.
  • Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. Tables of Bond Lengths Determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. J. Chem. Soc. Perkin Trans. 2 1987, 12, S1–S19. DOI: 10.1039/p298700000s1.
  • Yang, L.; Powell, D. R.; Houser, R. P. Structural Variation in Copper(I) Complexes with Pyridylmethylamide Ligands: Structural Analysis with a New Four-Coordinate Geometry Index, τ4. Dalton Trans. 2007, 9, 955–964. DOI: 10.1039/B617136B.
  • Cordero, B.; Gomez, V.; Platero-Prats, A. E.; Reves, M.; Echeverria, J.; Cremades, E.; Barragan, F.; Alvarez, S. Covalent Radii Revisited. Dalton Trans. 2008, 21, 2832–2838. DOI: 10.1039/B801115J.
  • Ke, C.-H.; Kuo, B.-C.; Nandi, D.; Lee, H. M. Monodentate Palladium Complexes Bearing Abnormal and Normal Carbene Ligands with a Formally Identical Steric Environment. Organometallics 2013, 32, 4775–4784. DOI: 10.1021/om4004219.
  • Teci, M.; Brenner, E.; Matt, D.; Gourlaouen, C.; Toupet, L. Directional Properties of Fluorenylidene Moieties in Unsymmetrically Substituted N-Heterocyclic Carbenes. Unexpected CH Activation of a Methylfluorenyl Group with Palladium. Use in Palladium Catalysed Suzuki-Miyaura Cross Coupling of Aryl Chlorides. Dalton Trans. 2014, 43, 12251–12262. DOI: 10.1039/C4DT01102C.
  • Onar, G.; Gürses, C.; Karataş, M. O.; Balcıoğlu, S.; Akbay, N.; Özdemir, N.; Ateş, B.; Alıcı, B. Palladium(II) and Ruthenium(II) Complexes of Benzotriazole Functionalized N-Heterocyclic Carbenes: Cytotoxicity, Antimicrobial, and DNA Interaction Studies. J. Organomet. Chem. 2019, 886, 48–56. DOI: 10.1016/j.jorganchem.2019.02.013.
  • Boubakri, L.; Yasar, S.; Dorcet, V.; Roisnel, T.; Bruneau, C.; Hamdi, N.; Ozdemir, I. Synthesis and Catalytic Applications of Palladium N-Heterocyclic Carbene Complexes as Efficient Pre-Catalysts for Suzuki-Miyaura and Sonogashira Coupling Reactions. New J. Chem. 2017, 41, 5105–5113. DOI: 10.1039/C7NJ00488E.
  • Gökçe, A. G.; Türkmen, H.; Aygün, M.; Çetinkaya, B.; Büyükgüngör, O. Synthesis and Structural Characterization of Palladium(II) Complex Bearing N-Heterocyclic Carbene. Struct. Chem. 2008, 19, 57–62. DOI: 10.1007/s11224-007-9249-8.
  • Karaca, E. Ö.; Gürbüz, N.; Şahin, O.; Büyükgüngör, O.; Özdemir, İ. Synthesis of Palladium Complexes Derived from Imidazolidin-2-Ylidene Ligands and Used for Catalytic Amination Reactions. Appl. Organometal. Chem. 2016, 30, 1050–1055. DOI: 10.1002/aoc.3541.
  • Fu, C.-F.; Lee, C.-C.; Liu, Y.-H.; Peng, S.-M.; Warsink, S.; Elsevier, C. J.; Chen, J.-T.; Liu, S.-T. Biscarbene Palladium(II) Complexes. Reactivity of Saturated versus Unsaturated N-Heterocyclic Carbenes. Inorg. Chem. 2010, 49, 3011–3018. DOI: 10.1021/ic9025188.
  • Özdemir, İ.; Demir, S.; Şahin, O.; Büyükgüngör, O.; Çetinkaya, B. Palladium N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Catalytic Properties in Amination. J. Organomet. Chem. 2010, 695, 1555–1560. DOI: 10.1016/j.jorganchem.2010.03.013.
  • Spek, A. L. Structure Validation in Chemical Crystallography. Acta Crystallogr. D Biol. Crystallogr. 2009, 65, 148–155. DOI: 10.1107/S090744490804362X.
  • Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. ‐L. Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555–1573. DOI: 10.1002/anie.199515551.
  • Spackman, M. A.; Jayatilaka, D. Hirshfeld Surface Analysis. CrystEngComm 2009, 11, 19–32. DOI: 10.1039/B818330A.
  • Tripathi, S.; Hossain, A.; Seth, S. K.; Mukhopadhyay, S. Quantitative Insights into the Crystal Structure of a Mixed-Ligand Co(III) Complex: Experimental and Theoretical Studies. J. Mol. Struct. 2020, 1216, 128207. DOI: 10.1016/j.molstruc.2020.128207.
  • Seth, S. K.; Sarkar, D.; Kar, T. Use of π–π Forces to Steer the Assembly of Chromone Derivatives into Hydrogen Bonded Supramolecular Layers: Crystal Structures and Hirshfeld Surface Analyses. CrystEngComm 2011, 13, 4528–4535. DOI: 10.1039/c1ce05037k.
  • Seth, S. K.; Sarkar, D.; Jana, A. D.; Kar, T. On the Possibility of Tuning Molecular Edges to Direct Supramolecular Self-Assembly in Coumarin Derivatives through Cooperative Weak Forces: Crystallographic and Hirshfeld Surface Analyses. Cryst. Growth Des. 2011, 11, 4837–4849. DOI: 10.1021/cg2006343.
  • Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976.
  • Aihara, J. Reduced HOMO-LUMO Gap as an Index of Kinetic Stability for Polycyclic Aromatic Hydrocarbons. J. Phys. Chem. A 1999, 103, 7487–7495. DOI: 10.1021/jp990092i.
  • Kim, K. H.; Han, Y. K.; Jung, J. Basis Set Effects on Relative Energies and HOMO-LUMO Energy Gaps of Fullerene C36. Theor. Chem. Acc. 2005, 113, 233–237. DOI: 10.1007/s00214-005-0630-7.
  • Seth, S. K.; Banerjee, S.; Kar, T. Crystal Structure and DFT Calculations of Andrographiside. J. Mol. Struct. 2010, 965, 45–49. DOI: 10.1016/j.molstruc.2009.11.036.
  • Seth, S. K.; Maity, G. C.; Kar, T. Structural Elucidation, Hirshfeld Surface Analysis and Quantum Mechanical Study of Para-Nitro Benzylidene Methyl Arjunolate. J. Mol. Struct. 2011, 1000, 120–126. DOI: 10.1016/j.molstruc.2011.06.003.
  • Seth, S. K.; Saha, N. C.; Ghosh, S.; Kar, T. Structural Elucidation and Electronic Properties of Two Pyrazole Derivatives: A Combined X-Ray, Hirshfeld Surface Analyses and Quantum Mechanical Study. Chem. Phys. Lett. 2011, 506, 309–314. DOI: 10.1016/j.cplett.2011.03.033.

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