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Spectroscopy Letters
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Volume 52, 2019 - Issue 9
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Articles

Charge transfer interaction and vibrational spectral investigation of 2-amino-5-nitropyridinium sulfamate

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Pages 492-509 | Received 29 Apr 2019, Accepted 20 Sep 2019, Published online: 18 Oct 2019

References

  • Koshima, H.; Hamada, M.; Yagi, I.; Uosaki, K. Synthesis, Structure and Second-Harmonic Generation of Noncentrosymmetric Cocrystals of 2-Amino-5-Nitropyridine with Achiral Benzenesulfonic Acids. Crystal Growth & Design 2001, 1, 467–471. DOI: 10.1021/cg015542m.
  • Horiuchi, N.; Kodaira, T.; Watanabe, A.; Matsuda, M. Protonation and Solvent-Interaction Effects on the First Hyperpolarizability of 2-Amino-5-Nitropyridine. Chemical Physics Letters 1997, 276, 92–96. DOI: 10.1016/S0009-2614(97)88039-6.
  • Fur, Y. L.; Beucher, M. B.; Masse, R.; Nicoud, J. F.; Levy, J. P. Crystal Engineering of Noncentrosymmetric Structures Based on 2-Amino-5-Nitropyridine and n-Chloroacetic Acid Assemblies. Chemistry of Materials 1996, 8, 68–75. DOI: 10.1021/cm9501731.
  • Watanabe, O.; Noritake, T.; Hirose, Y.; Okada, A.; Kurauchi, T. Synthesis, Crystal Structure and Nonlinear Optical Properties of 2-Amino-5-nitropyridine-L-(+)-Tartrate, a New Second-Harmonic-Generation Crystal. Journal of Materials Chemistry 1993, 3, 1053–1057. DOI: 10.1039/jm9930301053.
  • Sathya, K.; Dhamodharan, P.; Dhandapani, M. Structural Characterization and DFT Study of a New Optical Crystals: 2-Amino-3-Methylpyridinium-3,5-Dinitrobenzoate. Optics & Laser Technology 2018, 101, 328–340. DOI: 10.1016/j.optlastec.2017.11.027.
  • Pecaut, J.; Levy, J. P.; Masse, R. Structural Evidence in 2-Amino-5-Nitropyridinium Halides (Cl–, Br–) of Herringbone Motifs Favourable to Efficient Quadratic Non-Linear Optical Properties. Journal of Materials Chemistry 1993, 3, 999–1003. DOI: 10.1039/JM9930300999.
  • Sivasubramani, V.; Mohankumar, V.; Senthil Pandian, M.; Ramasamy, P. Synthesis, Crystal Growth, Physicochemical Properties and Quantum Chemical Investigations of a D–π–a Type Organic Single Crystal: 2-Amino-5-Nitropyridinium p-Phenolsulfonate (2A5NPP) for Nonlinear Optical (NLO) Applications. CrystEngComm 2017, 19, 5662–5678. DOI: 10.1039/C7CE01202K.
  • Babu, G. A.; Ramasamy, R. P.; Ramasamy, P.; Krishna Kumar, V. Synthesis, Crystal Growth, and Characterization of an Organic Nonlinear Optical Donor-π-Acceptor Single Crystal: 2-Amino-5-Nitropyridinium-Toluenesulfonate. Crystal Growth & Design 2009, 9, 3333–3337. DOI: 10.1021/cg9001384.
  • Manivannan, S.; Dhanuskodi, S.; Kirschbaum, K.; Tiwari, S. K. Design of an Efficient Solution Grown Semiorganic NLO Crystal for Short Wavelength Generation: 2-Amino-5-Nitropyridinium Tetrafluoroborate. Crystal Growth & Design 2005, 5, 1463–1468. DOI: 10.1021/cg049562a.
  • Manikandan, S.; Dhanuskodi, S. EPR of γ-Irradiated Single Crystals of 2-Amino-5-Nitro Pyridinium L-Tartrate: A NLO Material. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 2007, 67, 160–165. DOI: 10.1016/j.saa.2006.06.039.
  • Ibanez, A.; Levy, J. P.; Mouget, C.; Prieur, E. Crystal Growth of a Promising Nonlinear Optical Material: 2-Amino-5-Nitropyridinium Chloride. Journal of Solid State Chemistry 1997, 129, 22–29. DOI: 10.1006/jssc.1996.7213.
  • Bagieu-Beucher, M.; Masse, R.; Qui, D. T. Structural Investigations of Two 2‐Amino‐5‐Nitropyridinium Salts: C5H6N3O2+NO3- and (C5H6N3O2+)2CuCl42. Zeitschrift für anorganische und allgemeine Chemie 1991, 606, 59–71. DOI: 10.1002/zaac.19916060106.
  • Rajkumar, M. A.; Xavier, S. S. J.; Anbarasu, S.; Devarajan, P. A. Growth and Characterization Studies of an Efficient Semiorganic NLO Single Crystal: 2-Amino 5-Nitropyridinium Dihydrogen Phosphate (2A5NPDP) by Sankaranarayanan–Ramasamy Method. Optik 2016, 127, 2187–2192. DOI: 10.1016/j.ijleo.2015.10.239.
  • Aakeroy, C. B.; Beatty, A. M.; Nieuwenhuyzen, M.; Zou, M. A Structural Study of 2-Amino-5-Nitropyridine and 2-Amino-3-Nitropyridine: intermolecular Forces and Polymorphism. Journal of Materials Chemistry 1998, 8, 1385–1389. DOI: 10.1039/a800073e.
  • Rajkumar, M. A.; Xavier, S. S.; Anbarasu, J. S.; Devarajan, P. A. Growth and Characterization Studies of an Efficient Semiorganic NLO Single Crystal: 2-Amino 5-Nitropyridinium Sulfamate (2A5NPS) by Assembled Temperature Reduction (ATR) Method. Journal of Materials Chemistry 2016, 55, 153–159. DOI: 10.1016/j.optmat.2016.03.022.
  • Petrosyan, A. M.; Ghazaryan, V. V.; Giester, G.; Fleck, M. Sulfamates and Methanesulfonates of L-Arginine and L-Histidine. Journal of Molecular Structure 2018, 1163, 114–127. DOI: 10.1016/j.molstruc.2018.02.112.
  • Rajkumar, M. A.; Mohideen, M. N.; Xavier, S. S. J.; Anbarasu, S.; Devarajan, P. A. Crystal Structure of 2-Amino-5-Nitro-Pyridinium Sulfamate. Acta Crystallographica Section E: Crystallographic Communications 2015, E71, 231–233. DOI: 10.1107/S2056989015000365.
  • Kurtz, S. K.; Perry, T. T. A Powder Technique for the Evaluation of Nonlinear Optical Materials. Journal of Applied Physics 1968, 39, 3798–3813. DOI: 10.1063/1.1656857.
  • Adant, M.; Dupuis, M.; Bredas, J. L. Ab Initio Study of the Nonlinear Optical Properties of Urea: Electron Correlation and Dispersion Effects. International Journal of Quantum Chemistry 1995, 56, 497–507. DOI: 10.1002/qua.560560853.
  • Thanthiriwatte, K. S.; Nalin de Silva, K. M. Non-Linear Optical Properties of Novel Fluorenyl Derivatives—Ab Initio Quantum Chemical Calculations. Journal of Molecular Structure 2002, 617, 169–175. DOI: 10.1016/S0166-1280(02)00419-0.
  • Pulay, P.; Fogarasi, G.; Pang, F.; Boggs, J. E. Systematic Ab Initio Gradient Calculation of Molecular Geometries, Force Constants, and Dipole Moment Derivatives. Journal of the American Chemical Society 1979, 101, 2550–2560. DOI: 10.1021/ja00504a009.
  • Rauhut, G.; Pulay, P. Transferable Scaling Factors for Density Functional Derived Vibrational Force Fields. The Journal of Physical Chemistry A 1995, 99, 3093–3100. DOI: 10.1021/j100010a019.
  • Sundius, T. Molvib-A Flexible Program for Force Field Calculations. Journal of Molecular Structure 1990, 218, 321–326. DOI: 10.1016/0022-2860(90)80287-T.
  • Sundius, T. Scaling of Ab Initio Force Fields by MOLVIB. Vibrational Spectroscopy 2002, 29, 89–95. DOI: 10.1016/S0924-2031(01)00189-8.
  • Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
  • Polavarapu, P. L. Ab Initio Vibrational Raman and Raman Optical Activity Spectra. The Journal of Physical Chemistry A 1990, 94, 8106–8112. DOI: 10.1021/j100384a024.
  • Keresztury, G.; Chalmers, J. M.; Griffith, P. R. Raman Spectroscopy: Theory in Handbook of Vibrational Spectroscopy, vol. 1; John Wiley & Sons Ltd: New York, 2002.
  • Ravikumar, C.; Joe, I. H. Electronic Absorption and Vibrational Spectra and Nonlinear Optical Properties of 4-Methoxy-2-Nitroaniline. Physical Chemistry Chemical Physics 2010, 12, 9452–9460. DOI: 10.1039/b927190b.
  • Anderson, F. P.; Gallagher, J. F.; Kenny, P. T. M.; Lough, A. Redetermination of Para-Aminopyridine (Fampridine, EL-970) at 150 K. Acta Crystallographica Section E: Structure Reports Online 2005, E61, o1350–o1353. DOI: 10.1107/S1600536805010433.
  • John, C. J.; Amalanathan, M.; Twinkle, A. R.; Srinivasan, P.; Joe, I. H. Vibrational Spectra and First Order Hyperpolarizability Studies of Dimethyl Amino Pyridinium 4-Nitrophenolate 4-Nitrophenol. Spectrochimica Acta Part A 2011, 81, 151–161. DOI: 10.1016/j.saa.2011.05.086.
  • Saleh, Z. A.; Askar, F. W.; Ridha, S. M. A. Synthesis, Characterization and DFT Calculations of 1,4-Diphenyl-3-(p-Nitrophenylamino)-1,2,4-Triazolium Hydroxide Inner Salt (Nitronitron) by 1H NMR, FT-IR, UV/Vis and HOMO-LUMO Analysis. International Journal of Materials and Chemistry 2015, 5, 31–43.
  • Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint. Chemical Reviews 1988, 88, 899–926. DOI: 10.1021/cr00088a005.
  • Glendening, E. D.; Landis, C. R.; Weinhold, F. Natural Bond Orbital Methods. Wiley Interdisciplinary Reviews: Computational Molecular Science 2012, 2, 1–42. DOI: 10.1002/wcms.51.
  • Anitha, K.; Balachandran, V.; Narayanan, B. Experimental and Theoretical (FT-IR, FT-Raman) Vibrational Spectroscopic Analysis and Second-and Third-Order NLO Properties of a (2E)-1-(4-Bromophenyl)-3-(2-Chlorophenyl) Prop-2-en-1-One. International Journal of Current Research and Academic Review 2015, 3, 70–89.
  • Arul Dhas, D.; Joe, I. H.; Roy, S. D. D.; Balachandran, S. Nonplanar Property Study of Antifungal Agent Tolnaftate-Spectroscopic Approach. Spectrochimica Acta Part A 2011, 79, 993–1003. DOI: 10.1016/j.saa.2011.04.011.
  • Edwin, B.; Amalanathan, M.; Joe, I. H. Vibrational Spectra and Natural Bond Orbital Analysis of Organic Crystal L-Prolinium Picrate. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 2012, 96, 10–17. DOI: 10.1016/j.saa.2012.04.062.
  • Vuagnant, A. M.; Wagner, E. L. Vibrational Spectra and Structure of Solid Sulfamic Acid and the Sulfamate Ion. The Journal of Chemical Physics 1957, 26, 77–82. DOI: 10.1063/1.1743268.
  • Katiyar, R. S.; Krishnan, R. S. Raman and IR Spectra of Sodium and Calcium Sulphamates. Indian Journal of Pure and Applied Physics 1968, 6, 686.
  • Philip, D.; Eapen, A.; Aruldhas, G. Vibrational and Surface Enhanced Raman Scattering Spectra of Sulfamic Acid. Journal of Solid State Chemistry 1995, 116, 217–223. DOI: 10.1006/jssc.1995.1206.
  • Bellamy, L. J. The Infrared Spectra of Complex Molecules; John Wiley and Sons: New York, 1975.
  • Smith, B. Infrared Spectral Interpretation a Systematic Approach; CRC: Washington, DC, 1999.
  • Socrates, G. Infrared Characteristic Group Frequencies; John Wiley and Sons: New York, 1980.
  • Lin-Vein, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: New York, 1991.
  • Ramalingam, S.; Periandy, S.; Mohan, S. Vibrational Spectroscopy (FTIR and FTRaman) Investigation Using Ab Initio (HF) and DFT (B3LYP and B3PW91) Analysis on the Structure of 2-Amino Pyridine. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 2010, 77, 73–81. DOI: 10.1016/j.saa.2010.04.027.
  • Katritzky, A. R. The Infrared Spectra of Heteroaromatic Compounds. Quarterly Reviews, Chemical Society 1959, 13, 353–373. DOI: 10.1039/qr9591300353.
  • Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6th ed.; John Wiley & Sons: New York, 2003.
  • Hanai, K.; Maki, Y.; Kuwae, A. Vibrational Spectra of β-Lactams—III. Potassium 2-Azetidinone-1-Sulfonate and Its Isotopic Compounds. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 1993, 49, 1131–1137. DOI: 10.1016/0584-8539(93)80072-I.
  • Sperline, R.; Song, Y.; Freiser, H. FTIR-ATR Study of the Co-Adsorption of Benzophenone with Sodium Dodecyl Sulfate and Sodium Dodecylbenzenesulfonate Using Al2O3-Coated Optics. Colloids and Surfaces A: Physicochemical and Engineering Aspects 1994, 93, 111–126. DOI: 10.1016/0927-7757(94)02894-X.
  • Raj, A. S.; Muthusubramanian, P.; Krishnamurthy, N. Laser Raman Spectra of Potassium Sulphamate Single Crystal. Journal of Raman Spectroscopy 1981, 11, 127–130. DOI: 10.1002/jrs.1250110214.
  • Dhanabal, T.; Sethuram, M.; Amirthaganesan, G.; Das, S. K. Spectral, Thermal, Structural, Optical and Antimicrobial Activity Studies on 2-Methylimidazolinium picrate—An Organic Charge Transfer Complex. Journal of Molecular Structure 2013, 1045, 112–123. DOI: 10.1016/j.molstruc.2013.03.043.
  • Rodrigues, J. J.; Misoguti, L.; Nunes, F. D.; Mendonça, C. R.; Zilio, S. C. Optical Properties of L-Threonine Crystals. Optical Materials 2003, 22, 235–240. DOI: 10.1016/S0925-3467(02)00270-7.
  • Ramachandran, E.; Natarajan, S. Crystal Growth of Some Urinary Stone Constituents: III. In-Vitro Crystallization of L-Cystine and Its Characterization. Crystal Research and Technology 2004, 39, 308–312. DOI: 10.1002/crat.200310187.
  • Malik, T.; Kar, T.; Bocelli, G.; Musatti, A. Structural and Thermal Characterization of L-Arginine Dihydrate––A Nonlinear Optical Material. Crystal Research and Technology 2006, 41, 280–284. DOI: 10.1002/crat.200510574.
  • Ashwell, G. J.; Jefferies, G.; Hamilton, D. G.; Lynch, D. E.; Roberts, M. P. S.; Bahra, G. S.; Brown, C. R. Strong Second Harmonic Generation from Centrosymmetric Dyes. Nature 1995, 375, 385–388. DOI: 10.1038/375385a0.
  • Rieckoff, K. E.; Peticoals, W. L. Optical Second Harmonic Generation in Crystalline Amino Acids. Science 1965, 147, 610–611.
  • Wensheng, G.; Fang, G.; Chunsheng, W.; Qitao, L.; Guangyong, Z.; Dong, W.; Zhongsheu, S. SHG from Centrosymmetric Supermolecular Crystal. Science in China Series B-Chemistry 2002, 45, 276–280.
  • Pandi, P.; Peramaiyan, G.; Sudhahar, S.; Chakkaravarthi, G.; Mohan Kumar, R.; Bhagavannarayana, G.; Jayavel, R. Studies on Synthesis, Growth, Structural, Thermal, Linear and Nonlinear Optical Properties of Organic Picolinium Maleate Single Crystals. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 2012, 98, 7–13. DOI: 10.1016/j.saa.2012.08.018.
  • Suresh, S. Growth, Optical, Mechanical, Dielectric and Theoretical Properties of Picolinium Maleate NLO Single Crystal. Optik 2014, 125, 2826–2829. DOI: 10.1016/j.ijleo.2013.11.065.
  • Joseph, L.; Sajan, D.; Shettigar, V.; Chaitanya, K.; Misra, N.; Sundius, T.; Němec, I. Synthesis, Crystal Growth, Thermal Studies and Scaled Quantum Chemical Studies of Structural and Vibrational Spectra of the Highly Efficient Organic NLO Crystal:1-(4-Aminophenyl)-3-(3,4-Dimethoxyphenyl)-Prop-2-en-1-One. Materials Chemistry and Physics 2013, 141, 248. DOI: 10.1016/j.matchemphys.2013.05.007.
  • Jamelah, S.; Al-Otaibi, E. (FT-IR and FT-Raman Spectra) and Theoretical (Ab Initio/HF, DFT/B3LYP) Study of 2-Amino-5-Chloropyridine and 2-Amino-6-Chloropyridine. Chemistry and Materials Research 2015, 7, 2224–3224. DOI: 10.1016/j.saa.2014.08.013.
  • Mohamed, A. R.; Rekha, T. N.; Rajkumar, B. J. M.; Premkumar, S.; Jawahar, A.; Mathavan, T.; Benial, M. F. Conformational, Vibrational Spectroscopic, Nonlinear Optical Activity, and Structure–Activity Studies on 2-Hydroxy-3,5-Dinitropyridine: Combined Experimental and Density Functional Theory Approach. Spectroscopy Letters 2016, 49, 155–166. DOI: 10.1080/00387010.2015.1111242.
  • Sreelaja, P. V.; Ravikumar, C. Scaled Quantum Chemical Studies and Vibrational Spectra of Conjugated Structure 2-Benzylidenehydrazinecarbothioamide. Optics and Spectroscopy 2018, 125, 609–618. DOI: 10.1134/S0030400X18110292.
  • Parr, R. G.; Donnelly, R. A.; Levy, M.; Palke, W. E. Electronegativity: The Density Functional Viewpoint. The Journal of Chemical Physics 1978, 68, 3801–3807. DOI: 10.1063/1.436185.
  • Parr, R. G.; Szentpaly, L.; Liu, S. Electrophilicity Index. Journal of the American Chemical Society 1999, 121, 1922–1924. DOI: 10.1021/ja983494x.
  • Pearson, R. G. Hard and Soft Acids and Bases. Journal of the American Chemical Society 1963, 85, 3533–3539. DOI: 10.1021/ja00905a001.
  • Parr, R. G.; Pearson, R. G. Absolute Hardness: Companion Parameter to Absolute Electronegativity. Journal of the American Chemical Society 1983, 105, 7512–7516. DOI: 10.1021/ja00364a005.
  • Chattaraj, P. K.; Lee, H.; Parr, R. G. HSAB Principle. Journal of the American Chemical Society 1991, 113, 1855–1856. DOI: 10.1021/ja00005a073.
  • Chattaraj, P. K.; Schleyer, P. V. R. An Ab Initio Study Resulting in a Greater Understanding of the HSAB Principle. Journal of the American Chemical Society 1994, 116, 1067–1071. DOI: 10.1021/ja00082a031.
  • Chattaraj, P. K.; Giri, S. Stability, Reactivity, and Aromaticity of Compounds of a Multivalent Superatom. The Journal of Physical Chemistry A 2007, 111, 11116–11121. DOI: 10.1021/jp0760758.
  • Chitrambalam, S.; Manimaran, D.; Joe, I. H.; Rastogi, V. K.; Hassan, I. U. Synthesis, Hirshfeld Surface Analysis, Laser Damage Threshold, Third-Order Nonlinear Optical Property and DFT Computation Studies of Dichloro Bis(DL-Valine)Zinc(II): a Spectroscopic Approach. Optical Materials 2018, 75, 285–296. DOI: 10.1016/j.optmat.2017.10.003.
  • Tang, S. F.; Song, J. L.; Li, X. L.; Mao, J. G. Luminescent Lanthanide (III) Carboxylate − Phosphonates with Helical Tunnels. Crystal Growth & Design 2006, 6, 2322–2326. DOI: 10.1021/cg060248l.
  • Krishnakumar, M.; Karthick, S.; Thirupugalmani, K.; Babu, B.; Vinitha, G. Growth, Spectral, Optical, Laser Damage Threshold and DFT Investigations on 2-Amino 4-Methyl Pyridinium 4-Methoxy Benzoate (2A4MP4MB): A Potential Organic Third Order Nonlinear Optical Material for Optoelectronic Applications. Optics & Laser Technology 2018, 101, 91–106. DOI: 10.1016/j.optlastec.2017.11.012.

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