Theoretical investigations on the structural, spectroscopic, electronic and thermodynamic properties of (3-Oxo-3H-benzo[f]chromen-1yl) methyl N,N-dimethylcarbamodithioate-1ex

Kara, M.; Evecen, M.; Özdogan, T.

doi:10.1515/msp-2017-0064

Artykuł - szczegóły

Tytuł artykułu

Theoretical investigations on the structural, spectroscopic, electronic and thermodynamic properties of (3-Oxo-3H-benzo[f]chromen-1yl) methyl N,N-dimethylcarbamodithioate-1ex

Autorzy

Kara M. , Evecen M. , Özdogan T.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

DOI

10.1515/msp-2017-0064

Warianty tytułu

Języki publikacji

Abstrakty

Hartree-Fock and Density Functional Theory (B3LYP, B3PW91) calculations for the ground state of (3-Oxo-3Hbenzo[ f]chromen-1-yl) methyl N,N-dimethylcarbamodithioate have been presented and the calculated structural parameters and energetic properties have been compared with the available X-ray diffraction data. The vibrational frequencies have been calculated using optimized geometry of the molecule. The conformational properties of the molecule have been determined by computing molecular energy properties, in which torsional angle varied from -180° to +180° in steps of 10°. Moreover, natural bond orbital analysis and atomic charge analysis have been performed. Besides, HOMO and LUMO energies have been calculated and their pictures have been presented. Finally, molecular electrostatic potential and thermodynamic properties have been calculated. It is seen that the obtained theoretical results agree well with the available experimental values. In all the calculations, except for optimization and vibrational calculations, B3LYP level of theory with 6-311++G(d,p) basis set has been used.

Słowa kluczowe

chromene DFT HF NBO HOMO LUMO

Wydawca

De Gruyter

Czasopismo

Materials Science Poland

Rocznik

2017

Tom

Vol. 35, No. 3

Strony

560--575

Opis fizyczny

Bibliogr. 68 poz., rys., tab.

Twórcy

autor

Kara M.

Mechanical Engineering, Technology Faculty, Amasya University, 05100 Amasya, Turkey

autor

Evecen M.

meryem.evecen@amasya.edu.tr

Department of Physics, Faculty of Arts and Sciences, Amasya University, 05100 Amasya, Turkey

autor

Özdogan T.

Department of Computer and Teaching Technology Education, Education Faculty, Amasya University, 05100 Amasya, Turkey

Bibliografia

[1] EVANS B.E., RITTLE K.E., BOCK M.G., DIPARDO R.M., FREIDINGER R.M., WHITTER W.L., LUNDELL G.F., VEBER D.F., ANDERSON P.S., CHANG R.S.L., LOTTI V.J., CERINO D.J., CHEN T.B., KLING P.J., KUNKEL K.A., SPRINGER J.P., HIRSHFIELD J., J. Med. Chem., 31 (1988), 2235.
[2] Enraf-Nonius CAD-4 Express ’88 Software, Enraf-Nonius: Delft, Holland, 1988.
[3] HENRIETTE G., LORRAINE L., BETTINA H., CLEMENCE D., KELLY D., IRENEJ K., Mol. Cancer Ther., 3 (2004), 1375.
[4] LAURIN P., FERROUD D., KLICH M., DUPUISHAMELIN C., MAUVAIS P., LASSAIGNE P., BONNEFOY A., MUSICKI B., Bioorg. Med. Chem. Lett., 9 (1999), 2079.
[5] FYLAKTAKIDOU K.C., HADJIPAVLOU-LITINA D.J., LITINAS K.E., NICOLAIDES D.N., Curr. Pharm. Des., 10 (2004), 3813(30).
[6] KWANGWOO C., SONG-KYU P., MOOK K.H., YONGSEOK C., MYUNG-HWA K., CHUN-HO P., BO-YOUNG J., GYU C.T., HYUN-MOO C., HEEYOON L., HEE H.S., SOOK K.M., KY-YOUB N., GYOONHEE H., Bioorg. Med. Chem., 16 (2008), 530.
[7] SHARMA P.N., SHOEB A., KAPIL R.S., POPLI S.P., Indian J. Chem. B, 19 (1980), 938.
[8] SHARMA P.N., SHOEB A., KAPIL R.S., POPLI S.P., Indian J. Chem. B, 17 (1979), 299.
[9] NARESHKUMAR J., JIAYI X., RAMESH M.K., FUYONG D., GUO J.Z., EMMANUEL P., J. Med. Chem., 52 (2009), 7544.
[10] TRAYKOVA M., KOSTOVA I., Int. J. Pharm., 1 (2005), 29.
[11] DOSHI J.M., TIAN D., XING C., J. Med. Chem., 49 (2006), 7731.
[12] ALIAA M.K., MANAL M.K., EMAN K ABD EL-ALL, HEBA A.H. ELSHEMY, Int. J. Pharm. Res. Develop., 4 (2012), 310.
[13] NORTH A.C.T., PHILIPS D.C., MATHEWS F.S., Acta Cryst. A, 24 (1968), 351,
[14] KAMDAR N.R., HAVELIWALA D.D., MISTRY P.T., PATEL S.K., Medic. Chem. Res., 20 (2011), 854.
[15] SHARMA P.N., SHOEB A., KAPIL R.S., POPLI S.P., Phytochemistry, 20 (1981), 335.
[16] ELHAFEZ O.M.A., EL KHRISY E.D., BADRIA F., FATHY A.D., Arch. Pharm. Res., 26 (2003), 686.
[17] BHAT M.A., SIDDIQUI N., KHAN S.A., Acta Pol. Pharm., 65 (2008), 235.
[18] JONES G., JACKSON W.R., CHOI C., BERGMARK W.R., J. Phys. Chem., 89 (1985), 294.
[19] TRENOR S.R., SHULTZ A.R., LOVE B.J., LONG T.E., Chem. Rev., 104 (2004), 3059.
[20] HUNG T.T., LU Y.J., LIAO W.Y., HUANG C.L., IEEE Trans. Magn., 43 (2007), 867.
[21] KUMAR K.M., KOUR D., KAPOOR K., MAHABALESHWARAIAH N.M., KOTRESH O., GUPTA V. K., KANT R., Acta Cryst. E, 68 (2012), o878.
[22] EL-BAYOUKI K.A., ALY M.M., MOHAMED Y.A., BASYOUNI W.M., ABBAS S.Y., WJ Chem., 4 (2009), 161.
[23] THOMAS N.A.N.C.Y., ZACHARIAH S.M., Asian J. Pharm. Clin. Res., 6 (2013), 11.
[24] MAHABALESHWARAIAH N.M., RAVI H.R., VINDUVAHINI M., SREEPAD H.R., KOTRESH O., Acta Cryst. E, 68 (2012), o3001.
[25] FRISCH M.J., TRUCKS G.W., SCHLEGEL H.B., SCUSERIA G.E., ROBB M.A., CHEESEMAN J.R., SCALMANI G., BARONE V., MENNUCCI B., PETERSSON G.A., NAKATSUJI H., CARICATO M., LI X., HRATCHIAN H.P., IZMAYLOV A.F., BLOINO J., ZHENG G., SONNENBERG J.L., HADA M., EHARA M., TOYOTA K., FUKUDA R., HASEGAWA J., ISHIDA M., NAKAJIMA T., HONDA Y., KITAO O., NAKAI H., VREVEN T., MONTGOMERY JR. J.A., PERALTA J.E., OGLIARO F., BEARPARK M., HEYD J.J., BROTHERS E., KUDIN K.N., STAROVEROV V.N., KOBAYASHI R., NORMAND J., RAGHAVACHARI K., RENDELL A., BURANT J.C., IYENGAR S.S., TOMASI J., COSSI M., REGA N., MILLAM J.M., KLENE M., KNOX J.E., CROSS J.B., BAKKEN V., ADAMO C., JARAMILLO J., GOMPERTS R., STRATMANN R.E., YAZYEV O., AUSTIN A.J., CAMMI R., POMELLI C., OCHTERSKI J.W., MARTIN R.L., MOROKUMA K., ZAKRZEWSKI V.G., VOTH G.A., SALVADOR P., DANNENBERG J.J., DAPPRICH S., DANIELS A.D., FARKAS O., FORESMAN J.B., ORTIZ J.V., CIOSLOWSKI J., FOX D.J., Gaussian 09, Revision C.01, Gaussian, Inc.: Wallingford, CT, 2009.
[26] DENNINGTON R., KEITH T., MILLAM J., GaussView, Version 5, Semichem Inc.: Shawnee Mission, KS, 2009.
[27] ZHURKO G.A., ChemCraft, version 1.6 (build 304), 2009. http://www.chemcraftprog.com/.
[28] TANAK H., AGAR A.A., BÜYÜKGÜNGÖR O., Spectrochim. Acta A, 87 (2012), 15.
[29] SUNDARAGANESAN N., KALAICHELVAN S., MEGANATHAN C., JOSHUA B.D., CORNARD J., Spectrochim. Acta A, 71 (2008), 898.
[30] AHMED M.K., HENRY B.R., J. Phys. Chem., 90 (1986), 1737.
[31] RAMALINGAM S., PERIANDY S., GOVINDARAJAN M., MOHAN S., Spectrochim. Acta A, 75 (2010), 1308.
[32] SHELDRICK G.M., Acta Cryst., A 64 (2008), 112.
[33] BABU P.D., PERIANDY S., MOHAN S., RAMALINGAM S., JAYAPRAKASH B.G., Spectrochim. Acta A, 78 (2011), 168.
[34] SUNDARAGANESAN N., ILAKIAMANI S., SALEEM H., WOJICIECHOWSKI P.M., MICHALSKA D., Spectrochim. Acta A, 61 (2005), 2995.
[35] KRISHNAKUMAR V., JOHN XAVIER R., Indian J. Pure. Appl. Phys., 41 (2003), 597.
[36] KRISHNAKUMAR V., PRABAVATHI N., Spectrochim. Acta A, 71 (2008), 449.
[37] ALTUN A., GOLCUK K., KUMRU M., J. Mol. Struct., 637 (2003), 155.
[38] SINGH S.J., PANDEY S.M., Indian J. Pure. Appl. Phys., 12 (1974), 300.
[39] SINGH R.N., PRASAD S.C., Spectrochim. Acta A, 34 (1978), 39.
[40] SILVERSTEIN M., BASSLER G.C., MORRIL C., Spectro-scopic Identification of Organic Compounds, 5th Ed., John Wiley & Sons Inc., Singapore, 1991.
[41] ALTUN A., GOLCUK K., KUMRU M., J. Mol. Struct., 625 (2003), 17.
[42] DURIG J.R., BERGANA M.M., PHAN H.V., J. Raman Spectrosc., 22 (1991), 141.
[43] LITIVINOV G., Proceedings of the 13th International Conference on Raman Spectroscopy, Würzburg, Germany, 1992.
[44] GOVINDARAJAN M., GANASAN K., PERIANDY S., MOHAN S., Spectrochim. Acta A, 76 (2010), 12.
[45] SILVERSTEIN R.M., BASSELER G.C., MORILL C., Spectroscopic Identification of Organic Compounds, Wiley, New York, 1981.
[46] KARAKURT T., DINCER M., ÇUKUROVALI A., YILMAZ I., J. Mol. Struct., 991 (2011), 186.
[47] TECKLENBURG M.M.J., KOSNAK D.J., BHATNAGAR A., MOHANTY D.K., J. Raman Spectr., 28 (1997), 755.
[48] PAJAZK J., ROSPENK M., RAMAEKERS R., MAES G., GŁOWIAK T., SOBCZYK L., Chem. Phys., 278 (2002), 89.
[49] ARIVAZHAGAN M., KRISHNAKUMAR V., JOHNXAVIER R., ILANGO V., BALACHANDRAN K., Spectrochim. Acta A, 72 (2009), 941.
[50] VARASANYI G., Vibrational Spectra of Benzene Derivatives, Academic Press, New York, 1969.
[51] SILVERSTEIN R.M., WEBSTOR F.X., Spectrometric Identification of Organic Compounds, 6th Ed., JohnWilley & Sons, New York, 1998.
[52] COLTHUP N.B., DALY L.H., WIBERLY S.E., Introduction to Infrared and Raman Spectroscopy, 3rd Ed., Academic Press, Boston, MA, 1990.
[53] SOCRATES G., Infrared Characteristic Group Frequencies, John Wiley and Sons, New York, 1980.
[54] JAMES C., AMAL RAJ A., REGHUNATHAN R., HUBERT JOE I., JAYAKUMAR V.S., J. Raman Spect., 37 (2006), 1381.
[55] LIU J.N., CHEN Z.R., YUAN S.F., J. Zhejiang Univ. Sci. B, 6 (2005), 584.
[56] MUTHU S., PRASATH M., Spectrochim. Acta A, 115 (2013), 789.
[57] SCHWENKE D.W., TRUHLAR D.G., J. Chem. Phys., 82 (1985), 2418.
[58] GUTOWSKI M., CHALASINSKI G., J. Chem. Phys., 98 (1993), 4728.
[59] TANAK H., AGAR A.A., BÜYÜKGÜNGÖR O., Spectrochim. Acta A, 118 (2014), 672.
[60] MULLIKEN R.S., J. Chem. Phys., 23 (1955), 1833.
[61] JIAN F.F., ZHAO P.S., BAI Z.S., ZHANG L., Struct. Chem., 16 (2005), 635.
[62] FLEMING I., Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.
[63] OBOT I.B., JOHNSON A.S., Elixir Comp. Chem., 43 (2012), 6658.
[64] PIR H., GÜNAY N., AVCI D., TAMER Ö., TARCAN E., ATALAY Y., Arab. J. Sci. Eng., 39 (2014), 5799.
[65] SCROCCO E., TOMASI J., Adv. Quantum Chem., 11 (1979), 115.
[66] LUQUE F.J., LOPEZ J.M., OROZCO M., Theor. Chem. Acc., 103 (2000), 343.
[67] TANAK H., TOY M., J. Mol. Struct., 1068 (2014), 189.
[68] EVECEN M., TANAK H., Mater. Sci.-Poland, 34 (2016), 886.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-e30fe295-dba2-4170-9da2-1e2452a4eea3