Comment on “Density functional theory studies on molecular structure, vibrational spectra and electronic properties of cyanuric acid”

Prabhaharan, 2015, Density functional theory studies on molecular structure, vibrational spectra and electronic properties of cyanuric acid, Spectrochim. Acta A: Mol. Biomol. Spectrosc., 138, 711, 10.1016/j.saa.2014.11.037 No symmetry restrictions were imposed on the initial structures. Becke, 1988, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A, 38, 3098, 10.1103/PhysRevA.38.3098 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Vosko, 1980, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Can. J. Phys., 58, 1200, 10.1139/p80-159 Møller, 1934, Note on an approximation treatment for many-electron systems, Phys. Rev., 46, 618, 10.1103/PhysRev.46.618 Gaussian 09, Revision A.02, 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, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian Inc, Wallingford CT, 2009. Seifer, 2002, Cyanuric acid and cyanurates, Russ. J. Coord. Chem., 28, 301, 10.1023/A:1015531315785 Newman, 1952, Infrared spectra of cyanuric acid and deutero cyanuric acid, J. Am. Chem. Soc., 74, 3545, 10.1021/ja01134a026 Wiebenga, 1938, Crystal structure of cyanuric acid, Nature, 141, 122, 10.1038/141122b0 Wiebenga, 1938, Die Kristallstruktur der Cyanursäure (HCNO)3, Z. Kristallogr., 99, 217, 10.1524/zkri.1938.99.1.217 Wiebenga, 1952, Crystal structure of cyanuric acid, J. Am. Chem. Soc., 74, 6156, 10.1021/ja01143a548 Verschoor, 1964, X-ray diffraction study of the electron density distribution in cyanuric acid, Nature, 202, 1206, 10.1038/2021206b0 Verschoor, 1971, Electron density distribution in cyanuric acid. I. An X-ray diffraction study at low temperature, Acta Crystallogr., B27, 134, 10.1107/S0567740871001791 Dietrich, 1979, Acta Crystallogr., B35, 1191, 10.1107/S0567740879005860 Kutoglu, 1978, A simple refinement of density distributions of bonding electrons. IV. The distribution of valence electrons in cyanuric acid, Acta Crystallogr., B34, 1617, 10.1107/S0567740878006160 Guo, 2006, Contrasting solid-state structures of trithiocyanuric acid and cyanuric acid, Crystal Growth Des., 6, 846, 10.1021/cg0601094 Surinwong, 2014, Cyanuric acid: hydrothermal crystal growth and alternative crystallographic description, Chiang Mai J. Sci., 41, 414 Coppens, 1971, Electron density distribution in cyanuric acid. II. Neutron diffraction study at liquid nitrogen temperature and comparison of X-ray and neutron diffraction results, Acta Crystallogr., B27, 146, 10.1107/S0567740871001808 Klotz, 1947, Absorption spectra and tautomerism of cyanuric acid, melamine and some related compounds, J. Am. Chem. Soc., 69, 801, 10.1021/ja01196a017 Ito, 1953, The Raman spectrum of cyanuric acid, Bull. Chem. Soc. Japan, 26, 339, 10.1246/bcsj.26.339 Hirt, 1958, Ultraviolet absorption spectra of derivatives of symmetric triazine-II: oxo-triazines and their acyclic analogs, Spectrochim. Acta, 12, 127, 10.1016/0371-1951(58)80025-9 Sancier, 1964, Absorption spectra of solutions of cyanuric acid and its chlorinated derivatives, Spectrochim. Acta, 20, 397, 10.1016/0371-1951(64)80037-0 Nakamoto, 1955, Stretching frequencies as a function of distances in hydrogen bonds, J. Am. Chem. Soc., 77, 6480, 10.1021/ja01629a013 Padgett, 1957, Effects in the solid-state infrared spectrum of cyanuric acid, J. Chem. Phys., 26, 959, 10.1063/1.1743446 Shimanouchi, 1964, Far-infrared spectra of cyanuric acid, uracil, and diketopiperazine, J. Chem. Phys., 41, 2651, 10.1063/1.1726332 Montgomery, 2008, The chemistry of cyanuric acid (H3C3N3O3) under high pressure and high temperature, J. Phys. Chem. B, 112, 2644, 10.1021/jp073589y Pérez-Manríquez, 2011, Aromaticity in cyanuric acid, J. Mol. Model., 17, 1311, 10.1007/s00894-010-0825-2 Mukherjee, 2010, Gas-phase acid-base properties of melamine and cyanuric acid, J. Am. Soc. Mass Spectrom., 21, 1720, 10.1016/j.jasms.2010.06.002 Liang, 2004, Theoretical study on the mechanism of keto–enol isomerization for cyanuric acid and cyameluric acid, J. Mol. Struct. (Theochem), 672, 151, 10.1016/j.theochem.2003.11.020 Liang, 2007, Keto–enol tautomerization of cyanuric acid in the gas phase and in water and methanol, J. Mol. Struct. (Theochem), 816, 125, 10.1016/j.theochem.2007.04.010 Rostkowska, 2009, Analysis of the normal modes of molecules with D3h symmetry. Infrared spectra of monomeric s-triazine and cyanuric acid, Vib. Spectrosc., 49, 43, 10.1016/j.vibspec.2008.04.012 For a graphical comparison of theoretical infrared spectra with experiment, the calculated B3LYP/6-311++G(d, p) harmonic frequencies were scaled by a factor of 0.978. The scaled frequencies, together with the calculated infrared intensities, were used to convolute each peak with a Lorentzian function having a full width at half-maximum (fwhm) equal to 2cm−1, so that the integral band intensities correspond to the calculated infrared absolute intensity. The Synspec software [34] was used for this purpose. K.K. Irikura, Program Synspec; National Institute of Standards & Technology: Gaithersburg, MD; <http://www.ccl.net/cca/software/MS-DOS/synthetic-spectrum/SYNSPEC.TXT.shtml> (accessed June 20, 2015). Polavarapu, 1990, Ab initio vibrational Raman and Raman optical activity spectra, J. Phys. Chem., 94, 8106, 10.1021/j100384a024 Krishnakumar, 2004, Simulation of IR and Raman spectra based on scaled DFT force fields: a case study of 2-(methylthio)benzonitrile, with emphasis on band assignment, J. Mol. Struct., 702, 9, 10.1016/j.molstruc.2004.06.004 Michalska, 2005, The prediction of Raman spectra of platinum (II) anticancer drugs by density functional theory, Chem. Phys. Lett., 403, 211, 10.1016/j.cplett.2004.12.096 Initially, the calculated Raman activities were converted into Raman scattering intensities as described in references [35–37]. For a graphical comparison with experimental Raman spectra, the calculated B3LYP/6-311++G(d, p) harmonic frequencies were scaled by a factor of 0.978. The scaled frequencies, together with the calculated Raman scattering intensities, were used to convolute each peak with a Lorentzian function having a full width at half-maximum (fwhm) equal to 10cm−1, so that the integral band intensities correspond to the calculated Raman scattering intensity. The Synspec software [34] was used for this purpose. As pointed out by one of the referees, another very important omission of the work by PPSG is lack of commentaries about the aromaticity of cyanuric acid in the different configurations.