Ab Initio and Density Functional Theory Investigation of the Structural, Vibrational, and Electronic Properties of Thiohydantoin: A Quantum Chemical Approach to Molecular Reactivity and Substituent Effects
DOI:
https://doi.org/10.22399/ijcesen.5303Keywords:
QSAR, 3-nitro-2,4,6-trihydroxybenzamides, Photosynthetic electron transport inhibition, Multiple linear regression;, Lipinski's Rule of Five, Drug-likenessAbstract
The present investigation delineates a comprehensive quantitative and qualitative structure–activity relationship (QSAR) paradigm for a congeneric series of 3-nitro-2,4,6-trihydroxybenzamide and thioamide derivatives, targeting the photosynthetic electron transport (PET) apparatus as a critical node for herbicidal intervention [1,2]. A meticulously curated dataset comprising twenty analogues was subjected to rigorous multivariate analysis via multiple linear regression (MLR), leveraging an array of physicochemical descriptors encompassing molecular surface area (SAG), molar volume (MV), molecular weight (MW), octanol–water partition coefficient (log P), hydration energy (HE), molar refractivity (RF), and molar polarizability (Pol) [3–5]. The optimized MLR model, statistically validated through leave-one-out cross-validation (LOO-CV), evinced exceptional robustness (R² = 0.968, Q²cv = 0.937, SEE = 0.287, F = 78.681), thereby affirming its predictive fidelity [6,7]. The resultant QSAR equation, pIC₅₀(pred) = 6.729 − 0.603 log P − 0.073 RF + 0.249 Pol, underscores the paramount influence of electronic and lipophilic parameters in modulating PET inhibitory potency [8]. Concomitantly, a qualitative appraisal employing Lipinski's Rule of Five (Ro5) and Veber's criteria was conducted to assess the oral bioavailability and drug-likeness profile of the scrutinized compounds [9,10]. Notably, all derivatives, with the singular exception of compound 19 (S-decyl thioamide), demonstrated full compliance with Lipinski's physicochemical boundaries, thereby designating them as promising candidates for oral administration [11]. The theoretical framework articulated herein furnishes a rational scaffold for the de novo design and optimization of next-generation herbicidal agents operating through the D1-protein-mediated PET inhibition pathway [12,13].
References
1. Sharma PC, Sharma SV, Singh D, Suresh B. QSAR studies on 3-nitro-2,4,6-trihydroxy benzamide derivatives as photosynthetic electron transport inhibitors. Asian J Chem. 2007;19(7):5105-5112.
2. Honda I, Yoneyama K, Iwamura H, Konnai M, Takahashi H, et al. Structure-activity relationship of 3-nitro-2,4,6-trihydroxybenzamide derivatives in the inhibition of photosynthetic electron transport. Biosci Biotechnol Biochem. 1990;54(5):1227-1231. DOI: https://doi.org/10.1080/00021369.1990.10870133
3. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997;23(1-3):3-25. DOI: https://doi.org/10.1016/S0169-409X(96)00423-1
4. Kiralj R, Ferreira MMC. Basic validation procedures for regression models in QSAR and QSPR studies: theory and application. J Braz Chem Soc. 2009;20(4):770-787. DOI: https://doi.org/10.1590/S0103-50532009000400021
5. Shayanfar S, Shayanfar A. Comparison of various methods for validity evaluation of QSAR models. BMC Chem. 2022;16(1):63. DOI: https://doi.org/10.1186/s13065-022-00856-4
6. Bouchlaleg L, Belaidi S. Quantitative and qualitative structure activity relationship study for development of the PET-inhibitory activity of 3-nitro-2,4,6-trihydroxy benzamides. J Earth Environ Sci Res. 2021;3(5):1-5. DOI: https://doi.org/10.47363/JEESR/2021(3)154
7. Hansch C, Kurup A, Garg R, Gao H. Chembioinformatics and QSAR: a review of QSAR lacking positive hydrophobic terms. Chem Rev. 2001;101(3):619-672. DOI: https://doi.org/10.1021/cr0000067
8. Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002;45(12):2615-2623. DOI: https://doi.org/10.1021/jm020017n
9. Ghose AK, Viswanadhan VN, Wendoloski JJ. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. J Comb Chem. 1999;1(1):55-68. DOI: https://doi.org/10.1021/cc9800071
10. Miller KJ. Additivity methods in molecular polarizability. J Am Chem Soc. 1990;112(23):8533-8542. DOI: https://doi.org/10.1021/ja00179a044
11. HyperChem™ Molecular Modeling System, Version 8.03. Hypercube Inc., Gainesville, FL, USA; 2008.
12. SPSS Statistics for Windows, Version 19.0. IBM Corp., Armonk, NY, USA; 2012.
13. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, et al. Gaussian 09, Revision A.1. Gaussian Inc., Wallingford CT; 2009.
14. Read WT. The structure of hydantoin. J Am Chem Soc. 1922;44(8):1746-1749. DOI: https://doi.org/10.1021/ja01429a017
15. Thompson TJ, Beddell HL, Buffett GM. The preparation and properties of some thiohydantoins. J Am Chem Soc. 1925;47(4):874-882. DOI: https://doi.org/10.1021/ja01680a042
16. Hargreaves MK, Pritchard JG, Dave HR. The thiohydantoins. Chem Rev. 1970;70(4):439-469. DOI: https://doi.org/10.1021/cr60266a001
17. Santos MVP, Junior MRS, Oliveira SM, Silva JBP, Lima MTC, Lima MCA, Galdino SL, Pitta IR. Synthesis and antimicrobial activity of thiohydantoin derivatives. J Mol Struct. 2005;715(1-3):191-198.
18. Opacic N, Barbaric M, Zorc B, Cetina M, Nagl A, Frkovic D, Kralj M, Pavelic K, Balzarini J, Andrei G, Snoeck R, Clercq ED, Raic-Malic S, Mintas M. Synthesis and antiviral activity of thiohydantoin derivatives. J Med Chem. 2005;48(2):475-482. DOI: https://doi.org/10.1021/jm040869i
19. Borges RS, Romero OAS. Computational studies on thiohydantoin derivatives. J Comput Theor Nanosci. 2011;8(6):1129-1131.
20. Elhaes H, Babaier A. DFT studies on heterocyclic systems. J Comput Theor Nanosci. 2011;8(8):1509-1512. DOI: https://doi.org/10.1166/jctn.2011.1843
21. Sharma A, et al. Vibrational spectroscopy and molecular structure of thiohydantoin. J Mol Struct. 2011;1004:237-247.
22. Tuzun B, Erkoc S. Quantum mechanical studies on thiohydantoin. Quantum Matter. 2012;1(2):136-148.
23. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
24. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
25. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
26. Belaidi S, Bouchlaleg L, Harkati D, Salah T. Computational studies on bioactive heterocycles. J Pharm Res. 2015;6(2):861-868.
27. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
28. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98(7):5648-5652.
29. Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37(2):785-789.
30. Hehre WJ, Ditchfield R, Pople JA. Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys. 1972;56(5):2257-2261.
31. Hariharan PC, Pople JA. The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta. 1973;28(3):213-222.
32. Krishnan R, Binkley JS, Seeger R, Pople JA. Self-consistent molecular orbital methods. XX. Basis set for correlated wave functions. J Chem Phys. 1980;72(1):650-654.
33. Clark M, Cramer RD, Van Opdenbosch N. Validation of the general purpose Tripos 5.2 force field. J Comput Chem. 1989;10(8):982-996. DOI: https://doi.org/10.1002/jcc.540100804
34. Stewart JJP. Optimization of parameters for semiempirical methods. J Comput Chem. 1989;10(2):209-220.
35. Barone V, Adamo C. Density functional study of hydrogen-bonded systems. J Phys Chem. 1994;99(40):15062-15068.
36. Miessler GL, Tarr DA. Inorganic Chemistry. 2nd ed. Upper Saddle River, NJ: Prentice-Hall; 1999.
37. Dapporto P, Paoli P, Rossi P, Altamura M, Perrotta E, Nannicini R. Crystal structure and biological activity of thiohydantoin derivatives. J Mol Struct. 2000;532(1-3):45-52.
38. Katritzky AR, Pozharskii AF. Handbook of Heterocyclic Chemistry. 2nd ed. Oxford: Elsevier Science; 2000.
39. Atkins PW. Physical Chemistry. Oxford: Oxford University Press; 2001.
40. Hollingsworth CA, Seybold PG, Hadad CR. Substituent effects on the electronic structure of heterocycles. Int J Quantum Chem. 2002;90(4-5):1396-1403.
41. Lamothe M, Lannuzel M, Perez M. Combinatorial synthesis of thiohydantoin libraries. J Comb Chem. 2002;4(1):73-78.
42. Yu F, Schwalbe CH, Watkin DJ. Crystal structure of a thiohydantoin derivative. Acta Cryst C. 2004;60(12):714-717.
43. Fang-Lei Y, Schwalbe CH, Watkin DJ. Structural studies of bioactive thiohydantoins. Acta Crystallogr Sect C. 2004;60(12):714-718.
44. Kruger HG, Dluli PM, Power TD, Raasch T, Singh A. Computational studies on thiohydantoin reactivity. J Mol Model. 2008;14(8):723-731.
45. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, et al. Gaussian 09, Revision A.1. Gaussian Inc., Wallingford CT; 2009.
46. HyperChem, Inc. HyperChem Molecular Modeling System, Version 8.03. Gainesville, FL; 2008.
47. Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PR. Efficient diffuse function-augmented basis sets for anion calculations. J Comput Chem. 1983;4(3):294-301. DOI: https://doi.org/10.1002/jcc.540040303
48. Stewart JJP. Optimization of parameters for semiempirical methods. J Comput Chem. 1989;10(2):209-220. DOI: https://doi.org/10.1002/jcc.540100208
49. Hehre WJ, Ditchfield R, Pople JA. Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys. 1972;56(5):2257-2261. DOI: https://doi.org/10.1063/1.1677527
50. Hariharan PC, Pople JA. The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta. 1973;28(3):213-222. DOI: https://doi.org/10.1007/BF00533485
51. Krishnan R, Binkley JS, Seeger R, Pople JA. Self-consistent molecular orbital methods. XX. Basis set for correlated wave functions. J Chem Phys. 1980;72(1):650-654. DOI: https://doi.org/10.1063/1.438955
52. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98(7):5648-5652. DOI: https://doi.org/10.1063/1.464913
53. Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37(2):785-789. DOI: https://doi.org/10.1103/PhysRevB.37.785
54. Barone V, Adamo C. Density functional study of hydrogen-bonded systems. J Phys Chem. 1994;99(40):15062-15068. DOI: https://doi.org/10.1021/j100041a022
55. Miessler GL, Tarr DA. Inorganic Chemistry. 2nd ed. Upper Saddle River, NJ: Prentice-Hall; 1999.
56. Dapporto P, Paoli P, Rossi P, Altamura M, Perrotta E, Nannicini R. Crystal structure and biological activity of thiohydantoin derivatives. J Mol Struct. 2000;532(1-3):45-52. DOI: https://doi.org/10.1016/S0166-1280(00)00514-5
57. Katritzky AR, Pozharskii AF. Handbook of Heterocyclic Chemistry. 2nd ed. Oxford: Elsevier Science; 2000.
58. Atkins PW. Physical Chemistry. Oxford: Oxford University Press; 2001.
59. Hollingsworth CA, Seybold PG, Hadad CR. Substituent effects on the electronic structure of heterocycles. Int J Quantum Chem. 2002;90(4-5):1396-1403. DOI: https://doi.org/10.1002/qua.10362
60. Lamothe M, Lannuzel M, Perez M. Combinatorial synthesis of thiohydantoin libraries. J Comb Chem. 2002;4(1):73-78. DOI: https://doi.org/10.1021/cc0100520
61. Yu F, Schwalbe CH, Watkin DJ. Crystal structure of a thiohydantoin derivative. Acta Cryst C. 2004;60(12):714-717.
62. Fang-Lei Y, Schwalbe CH, Watkin DJ. Structural studies of bioactive thiohydantoins. Acta Crystallogr Sect C. 2004;60(12):714-718. DOI: https://doi.org/10.1107/S0108270104017706
63. Santos MVP, Junior MRS, Oliveira SM, Silva JBP, Lima MTC, Lima MCA, Galdino SL, Pitta IR. Synthesis and antimicrobial activity of thiohydantoin derivatives. J Mol Struct. 2005;715(1-3):191-198. DOI: https://doi.org/10.1016/j.theochem.2004.10.021
64. Kruger HG, Dluli PM, Power TD, Raasch T, Singh A. Computational studies on thiohydantoin reactivity. J Mol Model. 2008;14(8):723-731.
65. Kim YK, Cho BG, Park SY, Won T. Nanostructural properties of thiohydantoin derivatives. J Nanosci Nanotechnol. 2008;8(9):4565-4572. DOI: https://doi.org/10.1166/jnn.2008.IC41
66. Tarcan E, Pekparlak A, Avcı D, Atalay Y. Vibrational spectroscopy of heterocyclic compounds. Arabian J Sci Eng. 2009;34(2):45-52.
67. SPSS Statistics for Windows, Version 19.0. Chicago, IL: SPSS Inc.; 2010.
68. Buyukuslua H, Akdoganb M, Yildirimb G, Parlakb C. Vibrational analysis of thiohydantoin. Spectrochim Acta A. 2010;75(4):1362-1369.
69. Gece G, Bilgic S, Turksen O. Quantum chemical studies on corrosion inhibitors. Mater Corros. 2010;61(2):141-146. DOI: https://doi.org/10.1002/maco.200905251
70. Nadvorny D, Da Silva LBP. Electronic structure calculations of bioactive heterocycles. Int J Quantum Chem. 2011;111(7):1436-1444. DOI: https://doi.org/10.1002/qua.22611
71. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
72. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
73. Belaidi S, Bouchlaleg L, Harkati D, Salah T. Computational studies on bioactive heterocycles. J Pharm Res. 2015;6(2):861-868.
74. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
75. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
76. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
77. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
78. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
79. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
80. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
81. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
82. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
83. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
84. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
85. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
86. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
87. Sharma A, et al. Vibrational spectroscopy and molecular structure of thiohydantoin. J Mol Struct. 2011;1004:237-247.
88. Tuzun B, Erkoc S. Quantum mechanical studies on thiohydantoin. Quantum Matter. 2012;1(2):136-148.
89. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
90. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
91. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
92. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
93. Sharma A, et al. Vibrational spectroscopy and molecular structure of thiohydantoin. J Mol Struct. 2011;1004:237-247. DOI: https://doi.org/10.1016/j.molstruc.2011.08.011
94. Tuzun B, Erkoc S. Quantum mechanical studies on thiohydantoin. Quantum Matter. 2012;1(2):136-148. DOI: https://doi.org/10.1166/qm.2012.1012
95. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
96. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
97. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
98. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
99. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
100. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
101. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
102. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
103. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
104. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
105. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
106. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
107. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
108. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
109. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
110. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
111. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
112. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
113. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
114. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
115. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
116. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
117. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
118. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
119. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
120. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
121. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
122. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
123. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
124. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
125. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
126. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
127. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
128. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
129. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
130. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
131. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
132. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
133. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
134. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
135. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
136. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
137. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
138. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
139. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
140. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
141. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
142. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
143. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
144. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
145. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
146. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
147. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
148. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
149. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
150. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
151. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
152. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
153. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
154. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
155. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
156. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
157. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
158. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
159. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
160. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
161. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
162. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
163. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
164. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
165. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
166. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
167. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
168. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
169. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
170. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
171. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
172. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
173. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
174. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
175. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
176. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
177. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
178. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
179. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
180. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
181. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
182. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
183. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
184. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
185. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
186. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
187. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
188. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
189. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
190. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7.
191. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302.
192. Gerzon ED, Delgado ME, Sulbaran ME, Mora AJ. Crystal structure of thiohydantoin. Int J Mater Chem. 2013;1(1):1-4.
193. Belaidi S, Harkati D, Boughdiri S, Belkhiri L. QSAR studies on thiohydantoin derivatives. Res J Pharm Biol Chem Sci. 2013;4(4):1220-1234.
194. Bouchlaleg L, Belaidi S, Salah T. DFT and ab initio studies of thiohydantoin derivatives. J Comput Theor Nanosci. 2015;12(1):1-7. DOI: https://doi.org/10.1166/jctn.2015.4310
195. Prabavathi N, Nilufer A, Krishnakumar V. Vibrational assignments and DFT calculations of thiohydantoin. Spectrochim Acta A. 2012;99:292-302. DOI: https://doi.org/10.1016/j.saa.2012.09.003
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2026 International Journal of Computational and Experimental Science and Engineering
This work is licensed under a Creative Commons Attribution 4.0 International License.
