Ab Inito Calculations on Adipic Acid

Year 2013, Volume: 17 Issue: 3, 357 - 362, 01.06.2013

Mustafa Çetin Yusuf Atalay Davut Avcı

Abstract

Geometric optimization, vibrational spectra and GIAO (gauge including atomic orbital) C NMR, H NMR chemical shift calculations were carried out by using Hartree-Fock (HF) method and density functional method (B3LYP) with the 6-31G(d) basis set. These methods are proposed as a tool to be applied in the structural characterization of adipic acid, thus providing useful support in the interpretation of experimental NMR data and IR data. Parameters were related to the linear correlation plot of computed data versus experimental C NMR, H NMR chemical shifts values and IR data.

Keywords

DFT, HF, 13C NMR and 1H NMR spectra, IR spectra, GIAO

Adipik Asit Üzerine Ab İnitio Hesaplamaları

Abstract

Geometric optimization, vibrational spectra and GIAO (gauge including atomic orbital) 13C NMR, 1H NMR chemical shift calculations were carried out by using Hartree-Fock (HF) method and density functional method (B3LYP) with the 6-31G(d) basis set. These methods are proposed as a tool to be applied in the structural characterization of adipic acid, thus providing useful support in the interpretation of experimental NMR data and IR data. Parameters were related to the linear correlation plot of computed data versus experimental 13C NMR, 1H NMR chemical shifts values and IR data

Keywords

DFT, HF, 13C NMR ve 1H NMR spektrumlar, IR spektrumlar, GIAO

References

• T. H. Nguyen, D. E. Hibbs, S. T. Howard, J. Comput. Chem. 26 (2005) 133.
• Michaels AS, Colville AR. 1960. The effect of surface active agents on crystal growth rate and crystal habit. J. Phys Chem 63:13–19.
• Michaels AS, Tausch FW. 1961. Modification of growth rate and habit of adipic acid crystals with surfactants. J Phys Chem 64:1730–1737.
• L. Williams-Seton, R. J. Davey, H. F. Lieberman, R. G. Pritchard, J. of Pharmaceutical Sci., 89 (2000) 346.
• Y. Atalay, D. Avcı, A. Başoğlu, J. Mol. Struct. 787 (2006) 90-95.
• Yu. A. Abramov, A. V. Volkov, P. Coppens, Chem. Phys. Lett. 311 (1999) 81-86.
• N. C. Handy, P. E. Maslen, R. D. Amos, J. S. Andrews, C. W. Murray, G. J. Laming, Chem. Phys. Lett. 197 (1992) 506.
• G. Rauhut, P. Pulay, J. Phys. Chem. 99 (1995) 30
• S. Y. Lee, B. H. Boo, Bull Korean Chem. Soc. 17 (1996) 760.
• J. Casanovas, A. M. Namba, S. Leon, G. L. B. Aquino, G. V. J. da Silva, C. Aleman, J. Org. Chem. 66 (2001) 3775-3782.
• A. B. Sebag, D. A. Forsyth, M. A. Plante, J. Org. Chem. 66 (2001) 7967-7973.
• D. B. Chesnut, in Reviews in Computational Chemistry, vol. 8 (Eds: K. B. Lipkowitz, D. B. Boyd), VCH, New York, ch. 5 (1996) p. 245-297.
• A. C. J. de Dios, Prog. Nucl. Magn. Reson. Spectrosc. 29 (1996) 229-278.
• D. A. Forsyth, A. B. Sebag, J. Am. Chem. Soc. 119 (1997) 9483-9494.
• T. Helgaker, M. Jaszunski, K. Ruud, Chem. Rev. 99 (1999) 293-352.
• R. Ditchfield, J. Chem. Phys. 56 (1972) 5688.
• K. Wolinski, J. F. Hinton, P. Pulay, J. Am. Chem. Soc. 112 (1990) 8251-8260.
• J. R. Cheeseman, G. W. Trucks, T. A. Keith, M. J. Frisch, J. Chem. Phys. 104 (1996) 5497.
• P. Cimino, L. Gomez-Paloma, D. Duca, R. Riccio, G. Bifulco, Magn. Reson. Chem. 42 (2004) 26.
• R. A. Friesner, R. B. Murphy, M. D. Beachy, M. N. Ringnalda, W. Pollard, Thomas; B. D. Dunietz, Y. Cao, J. Phys. Chem. A 103 (1999) 1913.
• L. Rulìsek, Z. Havlas, Int. J. Quantum Chem. 91 (2003) 504.
• T. Ziegler, Density Funct. Methods, Chem. Mater. Sci. 69 (1997).
• J. Housty, M. Hospital, Acta Cryst 18 (1965) 693–697. http://www.aist.go.jp
• (private communication). G. Rauhut, S. Puyear, K. Wolinski and P. Pulay, J. Phys. Chem., 100 (1996) 6310-6316.
• R. Ditchfield, W. J. Hehre and J.A. Pople, J. Chem. Phys., 54 (1971) 724-728.
• R. Ditchfield, Mol. Phys. 27(4) (1974) 789-807. C.M. Rohlfing, L. C. Allen, R. Ditchfield, Chem. Phys. 87 (1984) 9-15.
• A. Frisch, A. B. Nielsen, A. J. Holder, Gaussview User Manual, Gaussian Inc., Pittsburg, 2001.
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Revision A.9, Gaussian, Inc., PittsburghPA, 2001.
• L. Thomas, T. Srikrishnan, Journal of Chem. Crystallogr. 33 (2003) 9.
• S. Y. Lee, Bull Korean Chem. Soc. 19(1) (1998)
• C. J. M. Wheeless, X. Zou, R. Liu, J. Phys. Chem. 99 (1995) 1248.
• S. Y. Lee, B. H. Boo, J. Phys. Chem. 100 (1996) 150
• Jr. L. G. Wade, Organic chem., Prentice Hall Inc., 19 V. P. Ananikov, Central Eur. J. of Cem., 2(1) (2004) 196-213.60, 53-56, 2006.