90
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Bioactive Small Molecule, Piperazinium Bis(4-Hydroxybenzenesulphonate) upon Spectral Investigation, Hirshfeld Surface Analysis, Molecular Docking and ADMET Prediction: A Complement DFT Calculations

, , , , &
Pages 8729-8751 | Received 24 Aug 2022, Accepted 17 Nov 2022, Published online: 29 Nov 2022

References

  • R. Bhuvaneswari, and K. Sakthi Murugesan, “Synthesis, Growth, Structural, Dielectric, Thermal, Linear and Nonlinear Properties of 8-Hydroxyquinolinium 3-Carboxy-4-Hydroxy Benzene Sulfonate Monohydrate Single Crystal,” Optical Materials 98, no. 2019 (2019): 109431.
  • Can-Cheng. Guo, He-Ping. Li, and Xiao-Bing. Zhang, “Study on Synthesis, Characterization and Biological Activity of Some New Nitrogen Heterocycle Porphyrins,” Bioorganic & Medicinal Chemistry 11, no. 8 (2003): 1745–51.
  • S. Gunasekaran, and B. Anita, “Spectral Investigation and Normal Coordinate Analysis of Piperazine,” Indian Journal of Pure and Applied Physics. 46 (2008): 833–8. http://nopr.niscpr.res.in/handle/123456789/3024.
  • T. Eicher, and S. Hauptmann, The Chemistry of Heterocycles, second ed., 2003.
  • G. Pallavi, O. Alam, M. Naim, F. Nawaz, M. Iqbal, and M. Alam, “Recent Advancement of Piperidine Moiety in Treatment of Cancer- a Review,” European Journal of Medicinal Chemistry 157, no. 2018 (2018): 480–502.
  • Ali Ahmed Abdulridha, Mahmood A. Albo Hay Allah, Sajjad Q. Makki, Yusuf Sert, Hamida Edan Salman, and Asim A. Balakit, “Inhibition of Carbon Steel in 1 M H2SO4 Using New Azo Schiff Compound: Electrochemical, Gravimetric, Adsorption, Surface and DFT Studies,” Journal of Molecular Liquids 315, no. 2020 (2020): 113690.
  • Mahmood A. Albo Hay Allah, Asim A. Balakit, Hamida Idan Salman, Ali Ahmed Abdulridha, and Yusuf Sert, “Yusuf Sert, New Heterocyclic Compound as Carbon Steel Corrosion Inhibitor in 1 M H2SO4, High Efficiency at Low Concentration: Experimental and Theoretical Studies,” Journal of Adhesion Science and Technology (2022): 1–23.
  • Asim A. Balakit, Sajjad Q. Makki, Yusuf. Sert, Fatih. Ucun, Mohammed B. Alshammari, Pall. Thordarson, and Gamal A. El-Hiti, “Synthesis, Spectrophotometric and DFT Studies of New Triazole Schiff Bases as Selective Naked-Eye Sensors for Acetate Anion,” Supramolecular Chemistry 32, no. 10 (2020): 519–26.
  • T. Suzuki, N. Fukazawa, K. San-Nohe, W. Sato, O. Yano, and T. Tsuruo, “Structure-Activity Relationship of Newly Synthesized Quinoline Derivatives for Reversal of Multidrug Resistance in Cancer,” Journal of Medicinal Chemistry 40, no. 13 (1997): 2047–52.
  • A. W. McConnaughie, J. Spychala, M. Zhao, D. Boykin, and W. D. Wilson, “Design and Synthesis of RNA-Specific Groove-Binding Cations: Implications for Antiviral Drug Design,” Journal of Medicinal Chemistry 37, no. 8 (1994): 1063–9.
  • David Havlı́ček, Jiřı́. Plocek, Ivan Němec, Róbert Gyepes, and Zdeněk Mička, “The Crystal Structure, Vibrational Spectra, and Thermal Behavior of Piperazinium(2+) Selenate Monohydrate and N, N′-Dimethylpiperazinium(2+) Selenate Dihydrate,” Journal of Solid State Chemistry. 150, no. 2 (2000): 305–15.
  • David Havlı́ček, Vı́t Chudoba, Ivan Němec, Ivana Cı́sařová, and Zdeněk Mička, “Preparation, Crystal Structure, Vibrational Spectra and Thermal Behaviour of Piperazinium (2+) Selenite Monohydrate and Piperazinium (2+) Diselenite,” Journal of Molecular Structure. 606, no. 1-3 (2002): 101–16.
  • Elif. Ünaldi, and Neslihan. Demir, “Investigation of Biological Activities of 4-Hydroxy-3-(2-Hydroxy-5-Methylbenzylideamino) Benzenesulphonic Acid,” Journal of Scientific Perspectives 3, no. 4 (2019): 379–88.
  • Karuppasamy. Pichan, Senthil Pandian. Muthu, and Ramasamy. Perumalsamy, “Crystal Growth and Characterization of Third Order Nonlinear Optical Piperazinium Bis(4-Hydroxybenzenesulphonate) (P4HBS) Single Crystal,” Journal of Crystal Growth 473, no. 2017 (2017): 39–54.
  • H. S. Nagendra Prasad, A. P. Ananda, S. Najundaswamy, S. Nagashree, L. Mallesha, B. P. Dayananda, H. S. Jayanth, and P. Mallu, “Design, Synthesis and Molecular Docking Studies of Novel Piperazine Metal Complexes as Potential Antibacterial Candidate against MRSA,” Journal of Molecular Structure 1232, no. 2021 (2021): 130047.
  • H. S. Nagendra Prasad, A. P. Ananda, T. N. Lohith, P. Prabhuprasad, H. S. Jayanth, N. B. Krishnamurthy, M. A. Sridhar, L. Mallesha, and P. Mallu, “Design, Synthesis, Molecular Docking and DFT Computational Insight on the Structure of Piperazine Sulfynol Derivatives as a New Antibacterial Contender against Superbugs MRSA,” Journal of Molecular Structure 1247 (2022): 131333.
  • Alaa Z. Omar, Tawfik M. Mosa, Samer K. El-Sadany, Ezzat A. Hamed, and Mohamed. El-Atawy, “Novel Piperazine Based Compounds as Potential Inhibitors for SARS-CoV-2 Protease Enzyme: Synthesis and Molecular Docking Study,” Journal of Molecular Structure 1245, no. 2021 (2021): 131020.
  • Sethupathi. Dharmalingam, and Ganesan Nangavalli. Muthukrishnan, “Physical and Theoretical Investigations on Piperazinium 3, 5-Dinitrobenzoate (PDNB) Single Crystal: A Potential Candidate for Third-Order Nonlinear Optical (NLO) Applications,” Journal of Molecular Structure 1250 (2022): 131815.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al, Gaussian 09, Revision C.02, Gaussian Inc., Wallingford CT, 2010.
  • P. Pulay, G. Fogarasi, G. Pongor, J. E. Boggs, and A. Vargha, “Combination of Theoretical ab Initio and Experimental Information to Obtain Reliable Harmonic Force Constants. Scaled Quantum Mechanical (QM) Force Fields for Glyoxal, Acrolein, Butadiene, Formaldehyde, and Ethylene,” Journal of the American Chemical Society 105, no. 24 (1983): 7037–47.
  • R. Dennington, T. Keith, and J. Millam, Gauss View, Version 5, Semichem Inc., ShawneeMission, KS, 2009.
  • S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, and M. A. Spackman, CrystalExplorer (Version 2.2), University of Western Australia,Crawley, Australia, 2010.
  • T. Lu, and F. Chen, “Multiwfn: A Multifunctional Wavefunction Analyser,” Journal of Computational Chemistry 33, no. 5 (2012): 580–92.
  • W. Humphrey, A. Dalke, and K. Schulten, “VMD: Visual Molecular Dynamics,” Journal of Molecular Graphics 14, no. 1 (1996): 33–8.
  • J. M. Yang, and C. C. Chen, “GEMDOCK: A Generic Evolutionary Method for Molecular Docking,” Proteins Struct Proteins 55, no. 2 (2004): 288–304.
  • D. S. Visualizer, “Accelrys Software Inc,” Discov. Studio Visual 2 (2005).
  • Swiss Institute of Bioinformatics, http://www.swissadme.ch/index.php.
  • Olfa Noureddine, Sofian Gatfaoui, Silvia Antonia Brandán, Houda Marouani, and Noureddine Issaoui, “Structural, Docking and Spectroscopic Studies of a New Piperazine Derivative, 1-Phenylpiperazine-1,4-Diium Bis(Hydrogen Sulfate),” Journal of Molecular Structure 1202 (2020): 127351.
  • P. Karthiga Devi, P. Viswanathan, and A. Ali Fathima Sabirneeza, “Synthesis, Growth, Spectroscopic, Thermal, Dielectric and DFT Studies of Piperazinium Bis (Trichloro Acetate),” Journal of Molecular Structure 1250 (2022): 131765.
  • T. Joselin. Beaula, P. Muthuraja, M. Dhandapani, and V. Bena. Jothy, “Effect of Charge Transfer Withspectral Analysis on the Antibacterial Compound 4-(Dimethyl Amino) Pyridine: 3,5-Dinitrobenzoic Acid: Experimental and Theoretical Perspective,” Journal of Molecular Structure. 1171, no. 2018 (2018): 511–26.
  • J. D. Deephlin Tarika, X. D. Divya Dexlin, S. Madhankumar, D. Deva. Jayanthi, and T. Joselin. Beaula, “Tuning the Computational Evaluation of Spectroscopic, ELF, LOL, NCI Analysis and Molecular Docking of Novel anti COVID-19 Molecule 4-Dimethylamino Pyridinium 3, 5-Dichlorosalicylate,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 259, no. 2021 (2021): 119907.
  • Computational Chemistry Comparison and Benchmark Data Base Release 21 August, 2020. NIST Stand. Ref. Database 101.
  • R. J. Gillespie, “The VSEPR Model Revisited,” Chemical Society Reviews 21, no. 1 (1992): 59–69.
  • Fernanda C. Bottega, Marcelo R. L. Oliveira, Camila V. Garcia, Daniele C. Menezes, Mayura M. M. Rubinger, and Laercio Zambolim, “Syntheses Characterization and Antifungal Activity of Tris(1,10-Phenanthroline) Iron(II) Bis,” Química Nova 36, no. 6 (2013): 803–7.
  • T. Joselin Beaula, A. Packiavathi, D. Manimaran, I. Hubert Joe, V. K. Rastogi, and V. Bena Jothy, “Quantum Chemical Computations, Vibrational Spectroscopic Analysis and Antimicrobial Studies of 2,3-Pyrazinedicarboxylic Acid,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 138 (2015): 723–35.
  • R. N. Singh, Amit. Kumar, R. K. Tiwari, Poonam. Rawata, and V. P. Gupta, “A Combined Experimental and Quantum Chemical (DFT and AIM) Study on Molecular Struc- Ture, Spectroscopic Properties, NBO and Multiple Interaction Analysis in a Novel Ethyl 4-[2- (Carbamoyl) Hydrazinylidene] -3,5-Dimethyl-1H Pyrrole-2-Carboxylate and Its Dimer,” Journal of Molecular Structure. 1035 (2013): 427–40.
  • D. Sajan, I. Hubert. Joe, V. S. Jayakumar, and J. Zaleski, “Structural and Electronic Contributions to Hyperpolarizability in Methyl p-Hydroxy Benzoate,” Journal of Molecular Structure. 785, no. 1-3 (2006): 43–53.
  • Brian C. Smith, Infrared Spectral Interpretation: A Systematic Approach (Boca Raton, FL: CRC Press, 1998.
  • D. Michalska, D. C. Bieńko, A. J. Abkowicz-Bieńko, and Z. Latajka, “Density Functional, Hartree-Fock, and MP2 Studies on the Vibrational Spectrum of Phenol,” The Journal of Physical Chemistry 100, no. 45 (1996): 17786–90.
  • C. James, V. S. Jayakumar, and I. Hubert. Joe, “Natural Bond Orbital Analysis and Vibrational Spectroscopic Studies of H-Bonded N,N′-Diphenylguanidinium Nitrate,” Journal of Molecular Structure 830, no. 1-3 (2007): 156–66.
  • M. Rajkumar, and A. Chandramohan, “Synthesis, Growth, Characterisation and Laser Damage Threshold Studies of N,N-Dimethylanilinium-3-Carboxy-4- Hydroxybenzenesulphonate Crystal: An Efficient SHG Material for Electrooptic Applications,” Optical Materials 66 (2017): 261–70.
  • Davide Romani, Isabel Salas Tonello, and Silvia Antonia Brandán, “Influence of Atomic Bonds on the Properties of the Laxative Drug Sodium Picosulphate,” Heliyon 2, no. 11 (2016): e00190.
  • A. A. El-Emam, A. S. Al-Tamimi, K. A. Al-Rashood, H. N. Misra, V. Narayan, O. Prasad, and L. Sinha, “Structural and Spectroscopic Characterization of a Novel Potential Chemotherapeutic Agent 3-(1-Adamantyl)-1-{[4-(2-Methoxyphenyl)Piperazin-1-yl]Methyl}-4-Methyl-1H-1,2,4-Triazole-5(4H)-Thione by First Principle Calculations,” Journal of Molecular Structure 1022, no. 2012 (2012): 49–60.
  • L. Pejov, M. Ristova, Z. Zdravkovski, and B. S. ˇ. Optrajanov, “Ab Initio Quantum Chemical and Experimental Study of Structure, Harmonic Vibrational Frequencies and Internal Ph-SO3 Torsion of Benzenesulfonate Anion,” Journal of Molecular Structure 524, no. 1-3 (2000): 179–88.
  • R. K. Singh, A. K. Singh, S. Siddiqui, M. Arshad, and A. Jafri, “Synthesis, Molecular Structure, Spectral Analysis and Cytotoxic Activity of Two New Aroylhydrazones,” Journal of Molecular Structure. 1135, no. 2017 (2017): 82–97.
  • G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivaties, Adam Hilger, London, 1974.
  • R. M. Silverstein, G. C. Bassler, and T. C. Morrill, In, Spectrometric Identification of or- Ganic Compounds, 3rd ed., John Wiley & Sons, New York, NY, 1974., 239.
  • D. Sajan, J. Binoy, B. Pradeep, K. Venkatakrishnan, V. B. Kartha, I. H. Joe, and V. S. Jayakumar, “NIR-FT Raman and Infrared Spectra and Ab Initio Computations of Glycinium Oxalate,” Spectrochimica Acta. 60A (2004): 173–80.
  • P. J. A. Ribeiro-Claro, M. G. B. Drew, and V. Felix, “C–H⋯O Bonded Dimers in 2-Methoxy-Benzaldehyde Studied by X-Ray Crystallography, Vibrational Spectroscopy, and ab Initio Calculations,” Chemical Physics Letters. 356, no. 3–4 (2002): 318–24.
  • N. P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, Wiley, New York, 1994.
  • Corentin Lefebvre, Gaëtan Rubez, Hassan Khartabil, Jean-Charles Boisson, Julia Contreras-García, and Eric Hénon, “Accurately Extracting the Signature of Intermolecular Interactions Present in the NCI Plot of the Reduced Density Gradient versus Electron Density,” Physical Chemistry Chemical Physics : PCCP 19, no. 27 (2017): 17928–36.
  • Corentin Lefebvre, Hassan Khartabil, Jean-Charles Boisson, Julia Contreras-García, Jean-Philip Piquemal, and Eric Hénon, “The Independent Gradient Model: A New Approach for Probing Strong and Weak Interactions in Molecules from Wave Function Calculations,” Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry 19, no. 6 (2018): 724–35.
  • F. L. Hirshfeld, “Bonded-Atom Fragments for Describing Molecular Charge Densities,” Theoretica Chimica Acta 44, no. 2 (1977): 129–38.
  • S. Janani, Hemamalini. Rajagopal, S. Muthu, S. Aayisha, and M. Raja, “Molecular Structure, Spectroscopic (FT- IR, FT- Raman, NMR), HOMO- LUMO, Chemical Reactivity, AIM, ELF, LOL and Molecular Docking Studies on 1- Benzyl - 4 - (N- Boc- Amino) Piperidine,” Journal of Molecular Structure 1230 (2021): 129657.
  • R. Parthasarathi, V. Subramanian, D. R. Roy, and P. K. Chattaraj, “Electrophilicity Index as a Possible Descriptor of Biological Activity,” Bioorganic & Medicinal Chemistry 12, no. 21 (2004): 5533–43.
  • Erik. Johnson, “Quantum Chemical Calculations Applied To Somo-Homo Conversion And Vibrationally Averaged Nmr Shielding Parameters”, 2019. Student Research Projects, Dissertations, and Theses-Chemistry Department. 99. https://digitalcommons.unl.edu/chemistrydiss/99.
  • Anil. Kumar, and Michael D. Sevilla, “SOMO-HOMO Level Inversion in Biologically Important Radicals,” The Journal of Physical Chemistry. B 122, no. 1 (2018): 98–105.
  • C. Dabora. Vincy, J. D. Deephlin Tarika, X. D. Divya Dexlin, A. Rathika, and T. Joselin. Beaula, “Exploring the Antibacterial Activity of 1, 2 Diaminoethane Hexanedionic Acid by Spectroscopic, Electronic, ELF, LOL, RDG Analysis and Molecular Docking Studies Using DFT Method,” Journal of Molecular Structure 1247 (2022): 131388.
  • Carolyn N. Virca, and Theresa M. McCormick, “DFT Analysis into the Intermediates of Nickel Pyridinethiolate Catalysed Proton Reduction,” Dalton Transactions (Cambridge, England : 2003) 44, no. 32 (2015): 14333–40.
  • Michel. Caffarel, Emmanuel. Giner, Anthony. Scemama, and Alejandro. Ramírez-Solís, “Spin Density Distribution in Open-Shell Transition Metal Systems: A Comparative Post-Hartree–Fock, Density Functional Theory, and Quantum Monte Carlo Study of the CuCl2 Molecule,” Journal of Chemical Theory and Computation 10, no. 12 (2014): 5286–96.
  • S. Premkumar, T. N. Rekha, R. Mohamed Asath, T. Mathavan, and A. Milton Franklin Benial, “Vibrational Spectroscopic, Molecular Docking and Density Functional Theory Studies on 2-Acetylamino-5-Bromo-6-Methylpyridine,” European Journal of Pharmaceutical Sciences : official Journal of the European Federation for Pharmaceutical Sciences 82 (2016): 115–25.
  • Andreas. Dreuw, and Martin. Head-Gordon, “Single-Reference ab Initio Methods for the Calculation of Excited States of Large Molecules,” Chemical Reviews 105, no. 11 (2005): 4009–37.
  • Fathima Rizwana B, Johanan Christian Prasana, S. Muthu, and Christina Susan Abraham, “Molecular Docking Studies, Charge Transfer Excitation and Wave Function Analyses (ESP, ELF, LOL) on Valacyclovir: A Potential Antiviral Drug,” Computational Biology and Chemistry 78 (2019): 9–17.
  • A. Guido, P. Cortona, B. Mennucci, and C. Adamo, “On the Metric of Charge Transfer Molecular Excitations: A Simple Chemical Descriptor,” Journal of Chemical Theory and Computation 9, no. 7 (2013): 3118–26.
  • M. Govindarajan, M. Karabacak, S. Periandy, and S. Xavier, “Vibrational Spectroscopic Studies, NLO, HOMO-LUMO and Electronic Structure Calculations of α, α, α -.Trichloro Toluene Using HF and DFT,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 94, no. 2012 (2012): 53–64.
  • CvijetaJakobušic’. Brala, Ivana. Fabijanic’, Ana Karkovic’. Markovic’, and Viktor. Pilepic, “The Average Local Ionization Energy and Fukui Function of L-Ascorbate,the Local Reactivity Descriptors of Antioxidant Reactivity,” Computational and Theoretical Chemistry 1049 (2014): 1–6.
  • Ashutosh. Kumar, Anjali. Pandey And, and Anil. Mishra, “Computational Study of Novel 2,3-Bis[(1-Methyl-1H-Imidazole-2-yl)Sulfanyl]Quinoxaline: Structural Aspects, Spectroscopic Investigation, HOMO-LUMO, MESP, NLO, ADMET Predictions and Molecular Docking Studies as Potential Biotin Carboxylase and Antibiotics Resistant Aminoglycoside Phosphotransferase APH(2")IVA Enzyme Inhibitor,” Asian Journal of Chemistry 32, no. 3 (2020): 706–26.
  • B. Agoram, Book Review: ADME and Translational Pharmacokinetics/Pharmacodynamics of Therapeutic Proteins (Hoboken, NJ: Wiley Online Library, 2017).
  • S. W. Siegert, and R. J. Holt, “Physicochemical Properties, Pharmacokinetics, and Pharmacodynamics of Intravenous Hematin: A Literature Review,” Advances in Therapy 25, no. 9 (2008): 842–57.
  • A. W. Bauer, W. M. Kirby, J. C. Sherris, and M. Truck, “Antibiotic Susceptibility Testing by a Standardized Single Disk Method,” American Journal of Clinical Pathology. 45, no. 98 (1996): 93–4. 4
  • Necmi Dege, Halil Gökce, Onur Erman Doğan, Gökhan Alpaslan, Tuğgan Ağar, S. Muthu, and Yusuf Sert, “Quantum Computational, Spectroscopic Investigations on N-(2-((2-Chloro-4,5-Dicyanophenyl)Amino) Ethyl)-4-Methylbenzenesulfonamide by DFT/TD-DFT with Different Solvents, Molecular Docking and Drug-Likeness Researches,” Colloids and Surfaces A: Physicochemical and Engineering Aspects 638, no. 2022 (2022): 128311.
  • M. Gümüş, S. N. Babacan, Y. Demir, Y. Sert, I. Koca, and I. Gülçin, “Discovery of Sulfadrug-Pyrrole Conjugates as Carbonic Anhydrase and Acetylcholinesterase Inhibitors,” Archiv Der Pharmazie. 355, no. 1 (2022): 2100242.
  • D. A. Filimonov, V. V. Poroikov, E. I. Karaicheva, R. K. Kazaryan, A. P. Boudunova, E. M. Mikhailovsky, A. V. Rudnitskih, L. V. Goncharenko, and Y. V. Burov, “Computer-Aided Prediction of the Biological Activity Spectrum of Chemical Compounds from Their Structural Formulae: PASS Systems,” Experimental and Clinical Psychopharmacology. 58 (1995): 56–62.
  • R. K. Goel, D. Singh, A. Lagunin, and V. Poroikov, “PASS-Assisted Exploration of New Therapeutic Potential of Natural Products,” Medicinal Chemistry Research 20, no. 9 (2011): 1509–14.
  • S. Jagadeesan, and S. Karpagam, “Novel Series of N -Acyl Substituted Indole Based Piperazine, Thiazole and Tetrazoles as Potential Antibacterial, Antifungal, Antioxidant and Cytotoxic Agents, and Their Docking Investigation as Potential Mcl-1 Inhibitors,” Journal of Molecular Structure 1271 (2023): 134013.
  • Y. Narasimha Reddy, Radhakrishna. Reddy Mardi, Nagaraja. Reddy G, Sreenivasulu. Reddy T, Kondaiah. Seku, Heba Mohamed. Fahmy, Shams H. Abdel-Hafez, Mahmoud M. Hessien, and Ahmed Esmail. Shalan, “One-Pot Synthesis of Novel Substituted Quinoxaline Piperazine Derivatives and Their Antimicrobial Activities,” Journal of Molecular Structure 1253 (2022): 132260.
  • K. R. Raghi, D. R. Sherin, M. J. Saumya, P. S. Arun, V. N. Sobha, and T. K. Manojkumar, “Computational Study of Molecular Electrostatic Potential, Docking and Dynamics Simulations of Gallic Acid Derivatives as ABL Inhibitors,” Computational Biology and Chemistry 74, no. 2018 (2018): 239–46.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.