One-Dimensional Hydrogen-Bonded N–H…O in the Hybrid Phosphate: Hirshfeld Surface Analysis and DFT Quantum Chemical Calculations
Affiliation:
1 Laboratory of Materials, Electrochemistry and Environment Faculty of Sciences,
Chemistry Department, Ibn Tofail University, Kenitra city, Morocco
2 Laboratory of Materials Chemistry and Biotechnology of Natural Products,
Moulay Ismail University, Meknes, Morocco
abdellatif.rafik@uit.ac.ma
DOI:
https://doi.org/10.23939/chcht15.03.359
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Abstract:
In the present work the 3D-supramolecular network is stabilized by N–H…O and O–H…O hydrogen bonds, by O…N interactions involving the organic cation and inorganic anion as checked by Hirshfeld surface analysis. The van der Waals contacts play a key role in the consolidation of the packing of 4-chloro-2-methylanilinium dihydrogenphosphate[4-CMDHP] structure. In order to support experimental results, density functional theory calculations have been performed using B3LYP functional with 3-21 G basis set. All of the obtained theoretical results are in a perfect agreement with the experimental ones. Furthermore, nonlinear optical behavior of 4-CMDHP has been investigated by determining the Hirshfeld surface, density of states and HOMO-LUMO energy gap using the same basis set. Finally, the molecular electrostatic potential surface of 4-CMDHP molecule was simulated and discussed.
References:
[1] Judeinstein P., Sanchez C.: J. Mater. Chem, 1996, 6, 511. https://doi.org/10.1039/JM9960600511
https://doi.org/10.1039/JM9960600511
[2] Adhikari S., Kar T., Seth S.: RSC Adv., 2016, 6, 99139. https://doi.org/10.1039/C6RA21466E
https://doi.org/10.1039/C6RA21466E
[3] Lehn J.-M.: Supramolecular Chemistry, 1st edn. Wiley-VCH, New York 1995. https://doi.org/10.1002/3527607439
https://doi.org/10.1002/3527607439
[4] Etter M., Frankenbach G.: Chem. Matter., 1989, 1, 10. https://doi.org/10.1021/cm00001a005
https://doi.org/10.1021/cm00001a005
[5] Vishweshwar P., McMahon J., Bis J., Zaworotko M.: J. Pharm. Sci., 2006, 95, 499. https://doi.org/10.1002/jps.20578
https://doi.org/10.1002/jps.20578
[6] Frisch M., Trucks G., Schlegel H. et al.: Gaussian 03, Gaussian, Inc. Wallingford CT, 2004.
[7] Dennington R., Keith T., Millam J.: Gauss View, Version 5, Semichem, Shawnee Mission KS, 2009.
[8] Clementi E., RoettiC.: Atom. Data Nucl. Data, 1974, 14, 177. https://doi.org/10.1016/S0092-640X(74)80016-1
https://doi.org/10.1016/S0092-640X(74)80016-1
[9] SpackmanM., Jayatilaka D.: Cryst. Eng. Comm., 2009, 11, 19. https://doi.org/10.1039/B818330A
https://doi.org/10.1039/B818330A
[10] Spackman M.: Phys. Scr., 2013, 87, 048103. https://doi.org/10.1088/0031-8949/87/04/048103
https://doi.org/10.1088/0031-8949/87/04/048103
[11] Turner M., McKinnon J., Jayatilaka D., Spackman M.: Cryst. Eng. Comm., 2011, 13, 1804. https://doi.org/10.1039/C0CE00683A
https://doi.org/10.1039/C0CE00683A
[12] McKinnon J., Jayatilaka D., Spackman M.: Chem. Commun., 2007, 161, 3814. https://doi.org/10.1039/b704980c
https://doi.org/10.1039/b704980c
[13] Spackman M., McKinnon J., Jayatilaka D.: Cryst. Eng. Comm., 2008, 10, 377. https://doi.org/10.1039/B715227B
https://doi.org/10.1039/b715227b
[14] Hirshfeld F.: Theor. Chim. Acta, 1977, 44, 129. https://doi.org/10.1007/BF00549096
https://doi.org/10.1007/BF00549096
[15] Luo Y., Mao Q., Sun B.: Inorg. Chim. Acta, 2014, 412, 60. https://doi.org/10.1016/j.ica.2013.12.005
https://doi.org/10.1016/j.ica.2013.12.005
[16] Luo Y., Sun B.: Cryst. Growth. Des., 2013, 13, 2098. https://doi.org/10.1021/cg400167w
https://doi.org/10.1021/cg400167w
[17] Desiraju G., Gavezzotti A.: Acta Crystallogr. B, 1989, 45, 473. https://doi.org/10.1107/S0108768189003794
https://doi.org/10.1107/S0108768189003794
[18] Wolff S., Grimwood D., McKinnon J. et al.: Crystal Explorer 3.1, University of Western Australia, Perth 2012.
[19] Scrocco E., Tomasi J.: Top. Curr. Chem., 1973, 42, 95. https://doi.org/10.1007/3-540-06399-4_6
https://doi.org/10.1007/3-540-06399-4_6
[20] Lipkowitz K., Boyd D. (Eds.): Reviews in Computational Chemistry, vol. 2. Wiley-VCM, New York 1991. https://doi.org/10.1002/9780470125793
https://doi.org/10.1002/9780470125793
[21] Naray-Szabo G., Ferenczy G.: Chem. Rev.,1995, 95, 829. https://doi.org/10.1021/cr00036a002
https://doi.org/10.1021/cr00036a002
[22] Jamroz M., Dobrowolski J., Brzozowski R.: J. Mol. Struct., 2006, 787, 172. https://doi.org/10.1016/j.molstruc.2005.10.044
https://doi.org/10.1016/j.molstruc.2005.10.044
[23] Bellamy L.: The infrared Spectra of Complex Molecules, vol. 2, 2nd edn. Chapman and Hall, London 1990.
[24] Fukui K.: Science, 1982, 218, 747. https://doi.org/10.1126/science.218.4574.747
https://doi.org/10.1126/science.218.4574.747
[25] Buyukuslu H., Akdogan M., Yildirim G., Parlak C.: Spectrochim. Acta A, 2010, 75, 1362. https://doi.org/10.1016/j.saa.2010.01.003
https://doi.org/10.1016/j.saa.2010.01.003
[26] Parr R., Donnelly R., Levy M., Palke W.: J. Chem. Phys., 1978, 68, 3801. https://doi.org/10.1063/1.436185
https://doi.org/10.1063/1.436185
[27] Parr R., Pearson R.: J. Am. Chem. Soc., 1983, 105, 7512. https://doi.org/10.1021/ja00364a005
https://doi.org/10.1021/ja00364a005
[28] Parr R., Szentpaly L., Liu S.: J. Am. Chem. Soc., 1999, 121, 1922. https://doi.org/10.1021/ja983494x
https://doi.org/10.1021/ja983494x
[29] Saeidian H., Sahandi M.: J. Mol. Struct., 2015, 1100, 486. https://doi.org/10.1016/j.molstruc.2015.07.069
https://doi.org/10.1016/j.molstruc.2015.07.069
[30] Gokçe H., Bahçeli S.: Spectrochim. Acta A, 2013, 114, 61. https://doi.org/10.1016/j.saa.2013.04.112
https://doi.org/10.1016/j.saa.2013.04.112
[31] Kohn W., Becke A., Parr R.: J. Phys. Chem., 1996, 100, 12974. https://doi.org/10.1021/jp960669l
https://doi.org/10.1021/jp960669l
[32] Seth S.K., Banerjee S., Kar T.: J. Mol. Struct., 2010, 965, 45. https://doi.org/10.1016/j.molstruc.2009.11.036
https://doi.org/10.1016/j.molstruc.2009.11.036
[33] Pearson R.: Proc. Natl. Acad. Sci. USA, 1986, 83, 8440. https://doi.org/10.1073/pnas.83.22.8440
https://doi.org/10.1073/pnas.83.22.8440
[34] Mulliken R.: J. Chem. Phys., 1955, 23, 1833. https://doi.org/10.1063/1.1740588
https://doi.org/10.1063/1.1740588
[35] Hoffmann R.: Solids and Surfaces: A Chemist's View of Bonding in Extended Structures. VCH Publ., New York 1988.
[36] Hughbanks T., Hoffmann R.: J. Am. Chem. Soc., 1983, 105, 3528. https://doi.org/10.1021/ja00349a027
https://doi.org/10.1021/ja00349a027
[37] Małecki J.: Polyhedron, 2010, 29, 1973. https://doi.org/10.1016/j.poly.2010.03.015
https://doi.org/10.1016/j.poly.2010.03.015
[38] O'Boyle N., Tenderholt A., Langner K.: J. Comp. Chem., 2008, 29, 839. https://doi.org/10.1002/jcc.20823
https://doi.org/10.1002/jcc.20823
[39] Chen M., Waghmare U., Friend C., Kaxiras E.: J. Chem. Phys., 1998, 109, 6854. https://doi.org/10.1063/1.477252
https://doi.org/10.1063/1.477252
[40] Mulliken R.: J. Am. Chem. Soc., 1952, 74, 811. https://doi.org/10.1021/ja01123a067
https://doi.org/10.1021/ja01123a067
[41] Mulliken R.: J. Chem. Phys., 1955, 23, 1833. https://doi.org/10.1063/1.1740588
https://doi.org/10.1063/1.1740588
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