Vibrational (FT-IR and FT-Raman), NMR and quantum chemical investigations on 7-Methylcoumarin

Abstract

In this article, the vibrational spectra of 7-Methylcoumarin were reported and discussed. The Infrared and Raman spectra of 7-Methylcoumarin in solid state were recorded in the region 4000-400 cm-1 and 3500-50 cm-1, respectively. The ground state spectroscopic and structural data of 7-Methylcoumarin were calculated utilizing Density Functional Theory (DFT) employing B3LYP functional that contains 6-311++G(d,p) and cc-pVDZ basis sets. After than the geometry optimization was performed, the vibrational frequencies were calculated. Furthermore, the total energy distribution (TED) of the vibration mode was determined based on the fundamental vibrational modes. These calculations were performed with PQS program using scaled quantum mechanics (SQM) method.

Keywords

• 7-Methylcoumarin
• DFT
• FT-IR and FT-Raman
• Molecular Structure and Vibrational spectra

References

1. 1. Alkorta I, Perez JJ, (1996) Molecular polarization potential maps of the nucleic acid bases. Int. J. Quantum Chem 57: 123–135.
2. 2. Bahgat K, (2006) Scaled quantum chemical studies of the structural and vibrational spectra of acetyl coumarin. Central Eur. J. Chem. 4 (4): 773–785.
3. 3. Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100.
4. 4. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652.
5. 5. Dennington R, Keith TA, Millam JM, GaussView, Version 6, Semichem Inc., Shawnee Mission, KS, 2016.
6. 6. Dereli Ö, Erdogdu Y, Gulluoglu MT, Türkkan E, Özmen A, Sundaraganesan N, (2012) Vibrational Spectral and Quantum Chemical Investigations of Tert-butyl-hydroquinone. J. Mol. Struct 1012: 168-176.
7. 7. Du XH, Hansell C, Doyle EPS, Caffrey CR, Holler TP, McKerrow JH, Cohen FE, (2002) Optimization of Blood–Brain Barrier Permeability with Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibitors Having a 2-Aminopyridine Scaffold. J. Med. Chem 45: 2690–2707.
8. 8. Erdogdu Y, (2013) Investigations of FT-IR, FT-Raman, FT-NMR spectra and quantum chemical computations of Esculetin molecule Spectrochim. Acta A: Mol. Biomol. Spectroscn 106: 25-33

9. 9. Erdogdu Y, Güllüoğlu MT, Kurt M, (2009) DFT, FT-Raman, FT-IR and NMR studies of 2-Fluorophenylboronic Acid J. Raman Spect 40(11): 1615-1623.
10. 10. Erdoğdu Y, Unsalan O, Amalanathan M, Joe IH, (2010) Infrared and Raman Spectra, Vibrational Assignment, NBO Analysis and DFT Calculations of 6-Aminoflavone. J. Mol. Struct., 980: 24-30.
11. 11. Frisch MJ. et all., Gaussian 16, Revision B.01, Gaussian, Inc., Wallingford CT, 2016.
12. 12. Güllüoğlu M T, Erdogdu Y, Karpagam J, Sundaraganesan N, Yurdakul Ş, (2011) DFT, FT-Raman, FT-IR and FT-NMR studies of 4-phenylimidazole J. Mol. Struct 990: 14-20.
13. 13. Halgren TA, (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem. 17: 490–519.
14. 14. Hoult JRS, Payá M, (1996) Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen Pharmacol. 27: 713-722.
15. 15. http://chemicalland21.com/lifescience/uh/methylcoumarin.htm
16. 16. http://en.wikipedia.org/wiki/Coumarin
17. 17. Jag M, (2001) Organic Spectroscopy – Principles and Alications, second ed., Narosa Publishing House, New Delhi.
18. 18. Joseph L, Sajan D, Reshmy R, Sasi BSA, Erdogdu Y, Thomas KK, (2012) Vibrational spectra, structural conformations, scaled quantum chemical calculations and NBO analysis of 3-acetyl-7-methoxycoumarin. Spectrochim. Acta 99: 234-247.
19. 19. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti cor- relation-energy formula into a functional of the electron density. Phys Rev B37:785–789
20. 20. Michalska D (2003) RAINT program. Wroclaw University of Technology, Poland
21. 21. Mishra A, Srivastava SK, Swati D, (2013) Study of structure–activity relationship of enantiomeric, protonated and deprotonated forms of warfarin via vibrational spectroscopy and DFT calculations. Spectrochim. Acta A: Mol. Biomol. Spectrosc.113: 439-446.
22. 22. Moghanian H, Mobinikhaledi A, Monjezi R, (2013) Synthesis, spectroscopy (vibrational, NMR and UV–vis) studies, HOMO–LUMO and NBO analysis of 8-formyl-7-hydroxy-4-methylcoumarin by ab initio calculations. J. Mol. Struct. 1052: 135-145.
23. 23. NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database Number 101, Release 12, 2005, Editor: Russell D. Johnson III, http://srdata.nist.gov/cccbdb.
24. 24. Ramoji A, Yenagi J, Tonannavar J, Jadhav VB, Kulkarni MV, (2007) Vibrational assignments and electronic structure calculations for 3-acetylcoumarin. Spectrochim. Acta . 68: 504–509.
25. 25. Sajan D, Erdogdu Y, Reshmy R, Dereli Ö, Thomas KK, Joe IH, (2011) DFT-based molecular modeling, NBO analysis and vibrational spectroscopic study of 3-(Bromoacetyl)coumarin. Spectrochim. Acta A: Mol. Biomol. Spectrosc 82: 118–125.
26. 26. Sancheti S, Sancheti S, Seo SY (2013) Ameliorative effects of 7-methylcoumarin and 7-methoxycoumarin against CCl4-induced hepatotoxicity in rats. Drug Chem Toxicol. 36(1): 42-47.
27. 27. Sarıkaya EK, Dereli Ö, (2014) Study on molecular structure and vibrational spectra of 5,7-dimethoxycoumarin using DFT: A combined experimental and quantum chemical approach. Optics and Spectroscopy. 117: 240-249.
28. 28. Sarıkaya EK, Dereli Ö, (2013a) Molecular structure and vibrational spectra of 7-Ethoxycoumarin by density functional method. J Mol Struct. 1052: 214–220.
29. 29. Sarıkaya EK, Dereli Ö, Erdogdu Y, Güllüoglu MT, (2013b) Molecular structure and vibrational spectra of 7-Ethoxycoumarin by density functional method. J Mol Struct. 1049: 220–226.
30. 30. Shah A., Naliapara Y., Sureja D., Motohashi N., Kawase M., Miskolci C., Szabo D., Molnar J. (1998) 6,12-Dihydro-1-Benzopyrano[3,4-b][1,4]Benzothiazin-6-ones Synthesis and MDR Reversal in Tumor Cells. Anticancer Res. 18: 3001–3004.
31. 31. Smith BC, (1998) Infrared Spectral Interpretation: A Systematic Aroach, CRC Press, Boca Raton, FL.
32. 32. Spartan 08, Wavefunction Inc., Irvine, CA 92612, USA, 2008.
33. 33. SQM version 1.0, Scaled Quantum Mechanical Force Field (2013) Green acres road. Fayetteville, Arkansas, p 72703
34. 34. Sri NU, Chaitanya K, Prasad MVS, Veeraiah V, Veeraiah A, (2012) FT-IR, FT-Raman and UV–Vis spectra and DFT calculations of 3-cyano-4-methylcoumarin. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 97: 728–736.
35. 35. Subashchandrabose S, Krishnan A R, Saleem H, Thanikachalam V, Manikandan G, Erdogdu Y, (2010) FT-IR, FT-Raman, NMR spectral analysis and theoretical NBO, HOMO–LUMO analysis of bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)ethane by ab initio HF and DFT methods J. Mol. Struc 981: 59-70.
36. 36. Varsanyi G, (1973) Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, s. 1–2, Academic Kiado, Budapest.
37. 37. Yavari I, Djahaniani H, Nasiri F, ( 2006) The crystal structure of tert-butyl coumarin-3-carboxylate. J. Iran. Chem. Soc 3: 46-50.
38. 38. Young D C, (2001) Computational Chemistry: A Practical Guide for Alying Techniques to Real World Problems, John Wiley & Sons, Canada.
39. 39. Zolek T, Paradowska K, Wawer I, (2003) 13C CP MAS NMR and GIAO-CHF calculations of coumarins. Solid State Nucl. Magn. Reson. 23: 77–87.