Spectroscopic and DFT studies of 2,4-dichloro-N-phenethylbenzenesulfonamide
-
R. Kavipriya
,
Jasmine P. Vennila
Abstract
The Fourier-transform infrared spectroscopy (FT-IR) spectrum of 2,4-dichloro-N-phenethylbenzenesulfonamide (DPBS) was obtained and the compound was studied theoretically. The optimized geometry, total electronic energy and vibrational wavenumbers of DPBS were examined using Hartree–Fock (HF) and density functional theory (DFT) method such as B3LYP, BP86 and M06 functionals with the basis set of 6-311++G(d,p) for all atoms. A complete vibrational assignment was studied for DPBS. The molecular orbital energies, polarizability and thermodynamic properties of DPBS were also computed. Analysis of molecular orbitals reveals the parameters such as chemical potential, chemical hardness and electrophilicity index. The molecular properties such as electric dipole moment µ, polarizability α, and hyperpolarizability β reveal the non-linear optical (NLO) property of DPBS. Natural bond analysis study reveals charge delocalization of the molecule. The experimental and computational results are found to have good agreement among themselves. The results of this work will pave the way for further insight in the study of the applications of DPBS.
Graphical Abstract:
Acknowledgements
The authors acknowledge the facilities from their respective Universities.
References
[1] Jagrut VB, Waghmare RA, Mane RA, Jadhav WN. An improved synthetic route for the synthesis of sulfonamides. Int J Chem Tech Res. 2011;3:1592.Suche in Google Scholar
[2] Supuran CT. Carbonic Anhydrase Inhibitors-Part 57:Quantum Chemical QSAR of a Group of 1,3,4-thiadiazole and 1,3,4-thiadiazoline Disulfonamides with Carbonic Anhydrase. Eur J Med Chem. 1999;34:41.10.1016/S0223-5234(99)80039-7Suche in Google Scholar
[3] Selvaag Edgar, Anholt Helle, Moan Johan, Thune Per. Inhibiting effects of antioxidants on drug-induced phototoxicity in cell cultures Investigations with sulphonamide-derived oral antidiabetics and diuretics. Journal of Photochemistry and Photobiology B: BiologyJournal. 1997;38:88–93.10.1016/S1011-1344(96)07433-7Suche in Google Scholar
[4] Supuran CT, Scozzaf A. Carbonic Anhydrase:its Inhibitors and Activators. Eur J Med Chem. 1999;34:799.10.1016/S0223-5234(99)00212-3Suche in Google Scholar
[5] Patel NB, Patel VN, Patel HR, Shaikh FM, Patel JC. Synthesis and Microbial Studies of (4-Oxo-thiazolidinyl) Sulphonamides Bearing Quinazolin-4-(3H)ones. Acta Poloniae PharmaceuticaActa. 2010;67(3):267–275.Suche in Google Scholar
[6] Supuran CT. Carbonic Anhydrase Inhibitors-Part 53-Synthesis of Substituted-Pyridinium Derivatives of Aromatic Sulfonamides:The First Non-Polymeric Membrane-Impermeable Inhibitors with Selectivity for Isozyme IV. Eur J Med Chem. 1998;31:577.10.1016/S0223-5234(98)80017-2Suche in Google Scholar
[7] Boyd AE. Sulfonylurea Receptors, Ion Channels and Fruit Flies, Diabetes. Diabetes. 1988;37:847.10.2337/diab.37.7.847Suche in Google Scholar PubMed
[8] Supuran CT. Recent Developments of Carbonic Anhydrase Inhibitors as Potential Anticancer Drugs. J Med Chem. 2008;51:3051–3056.10.1021/jm701526dSuche in Google Scholar PubMed
[9] Ozbek N, Katircioglu H, Karacan N, Baykal T. N-Ethyl-N-(2-methoxyphenyl)benzene sulphonamide. Bioorg Med Chem. 2007;15:5105–9.Suche in Google Scholar
[10] Ghorab MM, Ragab FA, Hamed MM. Design, Synthesis and Anticancer Evaluation of Novel Tetrahydroquinoline Derivatives Containing Sulfonamide Moiety. Eur J Med Chem. 2009;44:4211–17.10.1016/j.ejmech.2009.05.017Suche in Google Scholar PubMed
[11] Borne RF, Peden RL, Waters IW, Weiner M, Jordan R, Coats EA. Anti-Inflammatory Activity of para-Substituted N-benzenesulfonyl Derivatives of Anthranilic Acid. J Pharm Sci. 1974;63:615–17.10.1002/jps.2600630428Suche in Google Scholar PubMed
[12] Bhat MA, Imran M, Khan SA, Siddiqui N. Biological Activities of Sulfonamides. Indian J Pharm Sci. 2005;67:151–9.Suche in Google Scholar
[13] Babu CS, Kavitha HP. 2,4-Dichloro-N-phenethyl benzenesulphonamide. Act Cryst. 2009;E65:o921.10.1107/S1600536809010927Suche in Google Scholar PubMed PubMed Central
[14] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. GAUSSIAN 09, Revision D.01. Wallingford CT: Gaussian, Inc., 2013.Suche in Google Scholar
[15] Becke AD. Density-Functional Thermochemistry,III. The Role of Exact Exchange. J Chem Phys. 1993;91:5648.10.1063/1.464913Suche in Google Scholar
[16] Lee C, Yang W, Parr RG. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys Rev B. 1998;37:785.10.1103/PhysRevB.37.785Suche in Google Scholar
[17] Raghavachari K, Trucks GW. Highly Correlated Systems:Excitation Energies of First Row Transition Metals Sc-Cu. J Chem Phys. 1989;91:1062.10.1063/1.457230Suche in Google Scholar
[18] Wong MW, Wilberg KB, Frisch MJ. Solvent effects. Tautomeric Equilibria of Formamide and 2-pyridone in the Gas Phase and Solution: an ab initio SCRF study. J Am Chem Soc. 1992;114:1645.10.1021/ja00031a017Suche in Google Scholar
[19] Zhao Y, Truhlar DG. The MO6 Suite of Density Functionals for Main Group ThermoChemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States and Transition Elements: Two New Functionals and Systematic Testing of Four MO6-Class Functionals and 12 other Functionals. Theor Chem Accounts. 2008;120:215.10.1007/s00214-007-0310-xSuche in Google Scholar
[20] Pulay P, Fogarasi G, Pongar G, Boggs JE, Varsha A. Combination of Theoritical ab initio and Experimental Information to Obtain Reliable Harmonic Force Constants. Scaled Quantum Mechanical (QM) Force Fields for Glyoxal, Acrolein, Butadiene, Formaldehyde and Ethylene. J Am Chem Soc. 1983;105:7073.10.1021/ja00362a005Suche in Google Scholar
[21] Fogarasi G, Zhou X, Jaylor PW, Pulay P. The Calculation of ab initio Molecular Geometries: Efficient Optimization by Natural Internal Coordinates and Empirical Correction by Offset Forces. J Am Chem Soc. 1992;114:819.10.1021/ja00047a032Suche in Google Scholar
[22] Silverstein M, Bassler GC, Morill C. Spectrocopic identification of organic compounds. New York: John Wiley, 1981.Suche in Google Scholar
[23] Wilson EB, Decius JC, Cross PC. Molecular vibrations. New York: Dover Publ. Inc., 1980.Suche in Google Scholar
[24] Roeges NP. A guide to the complete interpretation of infrared spectra of organic structures. New York: Wiley, 1994.Suche in Google Scholar
[25] Arivazhagan M, Prabhakaran S, Gayathri R. Molecular Structure, VIbrational Spectroscopic, First HyperPolarizability, NBO and HOMO of P-Iodobenzene Sulfonyl Chloride. Spectrochim ActaA. 2011;82:332–9.10.1016/j.saa.2011.07.057Suche in Google Scholar PubMed
[26] Erdogdu Y, Gulluoglu MT, Yurdakul S. Molecular Structure and Vibrational Spectra of 1,3-bis(4-piperidyl)Propane by Quantum Chemical Calculations. J Mol Struct. 2008;889:361–70.10.1016/j.molstruc.2008.02.019Suche in Google Scholar
[27] Erdogdu Y, Gulluoglu MT. Analysis of Vibrational Spectra of 2 and 3-Methylpiperidine Based on Density Functional Theory Calculations. Spectrochim Acta. 2009;74A:361–70.10.1016/j.saa.2009.05.025Suche in Google Scholar PubMed
[28] George S. Infrared and characteristic group frequencies tables and charts, 3rd ed. Chichester: Wiley, 2001.Suche in Google Scholar
[29] Arivazhagan RM. Quantum Chemical Studies on Structure of 1,3-dibromo-5-Chlorobenzene. Spectrochim ActaA. 2011;82:316–26.10.1016/j.saa.2011.07.055Suche in Google Scholar PubMed
[30] Colthup NB, Daly LH, Wiberly SE. Introduction to infrared and Raman spectroscopy, 3rd ed. Boston, MA: Academic Press, 1990.Suche in Google Scholar
[31] Socrates G. Infrared characteristic group frequencies. New York: John Wiley and Sons, 1980.Suche in Google Scholar
[32] Sathyanarayana DN. Vibrational spectroscopy theory and applications. New Delhi: New Age International Publishers, 2004.Suche in Google Scholar
[33] Coates J. Interpretation of infrared spectra: A practical approach. New York: John Wiley & Sons Inc, 2000.Suche in Google Scholar
[34] Krishnakumar V, Prabhavathi N. Spectroscopic (FT-IR, FT-Raman, UV and NMR) Investigation, Conformational Stability, NLO Properties, HOMO-LUMO and NBO Analysis of Hydroxyquinoline Derivatives by Density Functional Theory Calculations. Spectrochim Acta A. 2008;71:449.10.1016/j.saa.2007.12.033Suche in Google Scholar
[35] Singh SJ, Pandey SM. Vibrational Spectra of 2-Amino-6-nitrotoluene. Indian J Pure Appl Phys. 1974;12:300.Suche in Google Scholar
[36] Altun A, Golcuk K, Kumru M. Structure and Vibrational Spectra of p-methylaniline: Hartree-Fock, MP2 and Density Functional Theory Studies. J Mol Struct (Theochem). 2003;637:155.10.1016/S0166-1280(03)00531-1Suche in Google Scholar
[37] Lin-Vein D, Colthup NB, Fateley WG, Grasseli JG. The hand book of infrared and Raman characteristic frequencies of organic molecules. San Diego: Academic Press, 1991.Suche in Google Scholar
[38] Subhashchandrabose S, Saleem H, Ergodu Y, Rajarajan G, Thanikachalam V. FT-Raman, FT-IR spectra and Total Energy Distribution of 3-pentyl-2,6-diphenylpiperidin-4-one:DFT method. Spectrochim ActaA. 2011;82:260–9.10.1016/j.saa.2011.07.046Suche in Google Scholar
[39] Parthasarathi R, Padmanabhan J, Subramanian V, Maiti B, Chattraj PK. Chemical Reactivity Profiles of Two-Selected Poly Chlorinated Biphenyls. J Phys Chem A. 2008;107:10346–52.10.1021/jp035620bSuche in Google Scholar
[40] Parr RG, Szentpaly LV, Liu SJ. Electrophilicity Index. J Am Chem Soc. 1999;121:1922.10.1021/ja983494xSuche in Google Scholar
[41] Singh RN, Kumar A, Tiwari RK, Rawat P. A Combined Experimental and Theoritical (DFT and AIM) Studies on Synthesis, Molecular Structure, Spectroscopic Properties and Multiple Interactions Analysis in a Novel Ethyl-4-[2-(thiocarbamoyl)hydrazinylidene]-3,5,dimethyl-1H-pyrrole-2-carboxylate and its Dimer. Spectrochim Acta. 2013;112:182–90.10.1016/j.saa.2013.04.002Suche in Google Scholar
[42] Murray JS, Sen K. Molecular electrostatic potentials, concepts and applications. Amsterdam: Elsevier, 1996.Suche in Google Scholar
[43] Fleming I. Frontier orbitals and organic chemical reactions. New York: John Wiley and Sons, 1976:5–27.Suche in Google Scholar
[44] Seminario JM. Recent developments and applications of modern density functional theory Vol. 4. Elsevier, 1996:800–6. Amsterdam.10.1016/S1380-7323(96)80082-3Suche in Google Scholar
[45] Yesikaynak T, Binzet G, Mehmet Emen F, Florke U, Kulcu N, Arsian H. Theoretical and Experimental Studies on N-(6-methylpyridin-2-yl-carbamothioyl)biphenyl-4-Carboxamide. Eur J Chem. 2010;1:1–5.10.5155/eurjchem.1.1.1-5.3Suche in Google Scholar
[46] Chidangil S, Shukla MK, Mishra PC. A Molecular Electrostatic Potential Mapping Study of some Fluoroquinolone Anti-bacterial Agents. J Mol Model. 1998;4:250–8.10.1007/s008940050082Suche in Google Scholar
[47] Reed AE, Weinhold F. Natural Localized Molecular Orbitals. J Chem Phys. 1985;83:1736–40.10.1063/1.449360Suche in Google Scholar
[48] Reed AE, Weinstock RB, Weinhold F. Natural Population Analysis. J Chem Phys. 1985;83:735–46.10.1063/1.449486Suche in Google Scholar
[49] Reed AE, Weinhold F. Natural Bond Orbital Analysis of Near-Hartree-Fock Water Dimer. J Chem Phys. 1983;78:4066–73.10.1063/1.445134Suche in Google Scholar
[50] Arjunan V, Raj A, Santhanam R, Marchewka MK, Mohan S. Structural, vibrational, electronic investigations and quantum chemical studies of 2-amino-4-methoxybenzothiazole. Spectrochim Acta A. 2013;102:327–40.10.1016/j.saa.2012.09.076Suche in Google Scholar PubMed
[51] Kavipriya R, Kavitha HP, Karthikeyan B, Natraj A. Molcular Structure, Spectroscopic (FT-IR, FT-Raman), NBO Analysis of N,N'-Diphenyl-6-piperidiny-1-yl-[1,3,5]-triazine-2,4-diamine. Spectrochim Acta A. 2015;156:476–87.10.1016/j.saa.2015.05.052Suche in Google Scholar PubMed
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Artikel in diesem Heft
- Process simulation approach in computer aided industrial design
- Novel technologies of nitrogen-based compounds
- Domino and one-pot syntheses of biologically active compounds using diphenylprolinol silyl ether
- Spectroscopic and DFT studies of 2,4-dichloro-N-phenethylbenzenesulfonamide
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Artikel in diesem Heft
- Process simulation approach in computer aided industrial design
- Novel technologies of nitrogen-based compounds
- Domino and one-pot syntheses of biologically active compounds using diphenylprolinol silyl ether
- Spectroscopic and DFT studies of 2,4-dichloro-N-phenethylbenzenesulfonamide
- Spirooxazine dyes
