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Synthesis, Growth, Crystal Structure and Characterization of the o-Toluidinium Picrate

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DOI: 10.4236/jcpt.2013.34020    3,893 Downloads   6,768 Views   Citations


A new organic charge transfer molecular complex salt of o-toluidinium picrate (OTP) was synthesised and the single crystals were grown by the slow solvent evaporation solution growth technique using methanol as a solvent at room temperature. Formation of the new crystal has been confirmed by single crystal X-ray diffraction (XRD) and NMR spectroscopic techniques. The crystal structure determined by single crystal X-ray diffraction indicates that both the cation and the anion are interlinked to each other by three types of intermolecular hydrogen bonds, namely N(4)-H(4A)···O(7), N(4)-H(4B)···O(5) and N(4)-H(4C)···O(7). The title compound (OTP) crystallizes in monoclinic crystal system with the centrosymmetric space group P21/c. Fourier transform infrared (FT IR) spectral analysis was used to confirm the presence of various functional groups in the grown crystal. The optical properties were analyzed by the UV-Vis-NIR and fluorescence emission studies.

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K. Mohana Priyadarshini, A. Chandramohan and T. Uma Devi, "Synthesis, Growth, Crystal Structure and Characterization of the o-Toluidinium Picrate," Journal of Crystallization Process and Technology, Vol. 3 No. 4, 2013, pp. 123-129. doi: 10.4236/jcpt.2013.34020.


[1] D. Josse, R. Hierle, I. Ledoux and J. Zyss, “Highly Efficient Second Harmonic Generation of Picoseconds Pulses at 1.32 μm in 3-Methyl-4-nitropyridine-1-oxide,” Applied physics Letters, Vol. 53, No. 23, 1988, pp. 2251-2253.
[2] B. F. Levine, C. G. Bethea, C. D. Thurmond, R. T. Lynch and J. L. Bernstein, “An Organic Crystal with an Exceptionally Large Optical Second Harmonic Coefficient: 2-Methyl-4-nitroaniline,” Journal of Applied Physics, Vol. 50, No. 4, 1979, pp. 2523-2527.
[3] P. Gunter, “Nonlinear Optics Laboratory,” ETH-Hong- gerberg, Zurich, 2009.
[4] R. Hierle, J. Badan and J. Zyss, “Growth and Characterization of a New Material for Nonlinear Optics: Methyl- 3-nitro-4-pyridine-1-oxide (POM),” Journal of Crystal Growth, Vol. 69, No. 2-3, 1984, pp. 545-554.
[5] R. S. Milliken, “Structures of Complexes Formed by Ha- logen Molecules with Aromatic and with Oxygenated Solvents,” Journal of American Chemical Society, Vol. 72, No. 1, 1950, pp. 600-608.
[6] M. M. H. Hamed, M. I. Abdel-Hanid and M. R. Mahmoud, “Molecular Complexes of Some N-Aryl-Dithiocarbamates with π-Electron Acceptors,” Monatshefte für Chemie, Vol. 129, No. 2, 1998, pp. 121-127.
[7] A. Chandramohan, R. Bharathikannan, V. Kandhavelu, J. Chandrasekaran and M. A. Kandhaswamy, “Synthesis, Crystal Growth, Structural, Thermal and Optical Proper- ties of Napthalene Picrate an Organic NLO Material,” Spectrochimica Acta Part A, Vol. 71, No. 3, 2008, pp. 755-759.
[8] A. Chandramohan, R. Bharathikannan, M. A. Kandha- samy, J. Chandrasekaran and V. Kandavelu, “Synthesis, Crystal Growth, Spectral, Thermal and Optical Properties of Acenaphthene Picrate,” Crystal Research Technology, Vol. 43, No. 1, 2008, pp. 93-98.
[9] A. Chandramohan, R. Bharathikannan, J. Chandrasekaran, P. Maadeswaran, R. Renganathan and V. Kandavelu, “Syn- thesis, Crystal Growth and Characterization of a New Organic NLO Material: Caffeinium Picrate (CAFP)—A Charge Transfer Molecular Complex Salt,” Journal of Crystal Growth, Vol. 310, No. 24, 2008, pp. 5409-5415.
[10] G. A. Babu, S. Sreedhar, S. V. Rao and P. Ramasamy, “Synthesis, Growth, Structural, Thermal, Linear and Nonlinear Optical Properties of a New Organic Crystal: Dimethylammonium Picrate,” Journal of Crystal Growth, Vol. 312, No. 12-13, 2010, pp. 1957-1962.
[11] H. Takayanagi, T. Kai, S. Yamaguchi, K. Takeda and M. Goto, “Studies on Picrate. VIII Crystal and Molecular Struc- tures of Aromatic Amine Picrates: Aniline, N-Methylaniline, N, N-Dimethylaniline and o-, m- and p-Phenyle- nediamine Picrates,” Chemical and Pharmaceutical Bulletin, Vol. 44, No. 12, 1996, pp. 2199-2204.
[12] P. Ramesh, R. Akalya, A. Chandramohan and M. N. Ponnusamy, “4-Aminopyridinium Picrate,” Acta Crystallographica Section E, Vol. 66, No. 4, 2010, Article ID: O1000.
[13] K. Muthu and S. Meenakshisundaram, “Crystal Growth, Structure and Characterization of p-Toluidinium Picrate,” Journal of Crystal Growth, Vol. 352, No. 1, 2012, pp. 163-166.
[14] C. Muthamizhchelvan, K. Saminathan, J. Fraanje, R. Peschar and K. Sivakumar, “3-Methylanilinium Picrate,” Acta Crystallographica Section E, Vol. 61, No. 4, 2005, pp. o1153-o1155.
[15] C. Muthamizhchelvan, K. Saminathan, J. Fraanje, R. Pes- char and K. Sivakumar, “Crystal Structure of 2-Cholroanilinium Picrate,” Analytical Sciences, Vol. 21, No. 4, 2005, pp. x61-x62.
[16] G. Smith, U. D. Wermuth and P. C. Healy, “A Second Crystal Polymorph of Anilinium Picrate,” Acta Crystallographica Section E, Vol. 60, No. 10, 2004, pp. o1800-o1803.
[17] V. K. Kumar and R. Nagalakshmi, “Vibrational Spectro- scopic Studies of an Organic Non-Linear Optical Crystal 8-Hydroxy Quinolinium Picrate,” Spectrochimica Acta Part A, Vol. 66, No. 4-5, 2007, pp. 924-934.
[18] G. Anandha Babu, A. Chandramohan, P. Ramasamy, G. Bhagavannarayana and B. Varghese, “Synthesis, Structure, Growth and Physical Properties of a Novel Organic NLO Crystal: 1,3-Dimethylurea Dimethylammounium Picrate,” Materials Research Bulletin, Vol. 46, No. 3, 2011, pp. 464-468.
[19] A. Chandramohan, R. Bharathikannan, M. A. Kandhaswamy, J. Chandrasekaran, R. Renganathan and V. Kandavelu, “Synthesis, Spectral, Thermal and NLO Properties of N,N-Dimethyl Anilinium Picrate,” Crystal Research and Technology, Vol. 43, No. 2, 2008, pp. 173- 178.
[20] G. M. Sheldrick, “SHELXL-97, Program for X-Ray Crystal Structure Refinement,” University of Gottingen, Gottingen, 1997.
[21] H. H. Willard, L. L. Merritt, J. A. Dear and F. A. Settle, “Instrumental Methods of Analysis,” 6th Edition, Wadsworth Publishing Company, Belmont, 1986.

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