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Siklopentolat Molekülünün Yapısal, Spektroskopik (FT-IR, Raman, NMR ve UV-Vis.) ve Teorik Olarak İncelenmesi

Yıl 2020, , 314 - 333, 20.03.2020
https://doi.org/10.18185/erzifbed.632227

Öz

Bu çalışmada siklopentolat molekülünün yapısal ve
spektroskopik karakterizasyonları (FT-IR, Laser-Raman,
1H ve 13C
NMR ve görünür UV spektrumları) deneysel ve teorik yöntemler kullanılarak
incelendi. Molekülün dört adet konformasyon yapısı ve optimize edilmiş
moleküler geometrileri incelendi. En kararlı form için molekülün titreşimsel
dalga-boyları,
1H ve 13C NMR kimyasal kaymaları, görünür
UV (UV-Vis) parametreleri teorik olarak elde edildi ve HOMO-LUMO analizleri
DFT/B3LYP yöntemi ile aug-cc-pVDZ temel seti kullanılarak gerçekleştirildi.
O45-H46…N23 grubundaki zayıf molekül-içi hidrojen bağ etkileşimi belirlendi. Teorik
titreşim mod atamaları VEDA 4 yazılımı kullanılarak potansiyel enerji dağılımı
(PED) cinsinden elde edildi. Teorik ve deneysel yöntemlerle elde edilen
verilerin birbirleri ile tutarlı oldukları belirlendi.  

Kaynakça

  • Akyıldırım, O., Gökce, H., Bahçeli, S. and Yüksek, H. (2017). “Theoretical and spectroscopic (FT-IR, NMR and UV-Vis.) characterizations of 3-p-chlorobenzyl-4-(4-carboxybenzy lidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one molecule”, Journal of Molecular Structure, 1127, 114-123.
  • Ambujakshan, K. R., Madhavan, V.S., Varghese, H.T., Panicker, C. Y., Temiz-Arpaci, O., Tekiner-Gulbas B. and Yildiz I. (2008). “Vibrational spectroscopic studies and ab initio calculations of 5-methyl-2-(p-methylaminophenyl)benzoxazole, Spectrochim”. Spectrochimica Acta Part A, 69, 782-788.
  • Angelova, O., Macicek, J., Vassilev, N.G., Momchilova, S. and Petrova, J. (1992). “Structures of threo (RR,SS) diethyl ester of 2-hydroxy-1,2-diphenylethylphosphonic acid and (±)diethyl ester of (1-hydroxycyclopentyl)(2-methylphenyl) methylphosphonic acid”, J. Crystallogr. Spectrosc. Res., 22, 253-258.
  • Becke, A.D. (1993). “Density-functional thermochemistry. III. The role of exact Exchange”, J. Chem. Phys. 98, 5648-5652.
  • Bilkan, M. T. (2017). “Structural and spectroscopic studies on dimerization and solvent-ligand complexes of Theobromine”. Journal of Molecular Liquids, 238, 523–532.
  • Colthup, N.B., Daly, L.H. and Wiberley, E. (1964). Introduction to Infrared and Raman Spectroscopy, Academic Press, New York.
  • Dennington, R., Keith, T. and Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
  • Ditchfield, R. (1974). “Self-consistent perturbation theory of diamagnetism. I. A gauge-invariant LCAO method for N.M.R. chemical shifts”, Molecular Physics, 27, 789-807.
  • Farhood, Q. K. (2012). “Cycloplegic Refraction in Children with Cyclopentolate versus Atropine“, Journal of Clinical and Experimental Ophthalmol., 3(7), 1-5.
  • Frag, E. Y. Z., Mohamed, G.G., El-Dien F.A.N., and Mohamed, M. El-Badry. (2011). “The Use of Integrated Analytical Tools for Determination of Cyclopentolate and Naphazoline Hydrochlolrides in Pure and Pharmaceutical Preparations”, Pharmaceutica Analytica Acta, 2(1), 1-6.
  • Frisch, M.J. et al. (2009). Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT.
  • Fukui, K. (1982). “Role of frontier orbitals in chemical reactions”, Science, 218, 747-754.
  • H. Buyukuslu, M. Akdogan, G. Yildirim and C. Parlak. (2010). “Ab initio Hartree-Fock and density functional theory study on characterization of 3-(5-methylthiazol-2-yldiazenyl)-2-phenyl-1H-indole”, Spectrochim. Acta Part A, 75, 1362-1369.
  • H. Gökce and S. Bahçeli. (2013). “The molecular structures, vibrational spectroscopies (FT-IR and Raman) and quantum chemical calculations of n-alkyltrimethylammonium bromides”. Opt. Spectrosc, 115, 632-644.
  • Hirschler, J., Berger, B. and Bolte, M. (1994). “A dimeric (phenylsulfonyl) oxazolidine”, Acta Crystallographica, C50, 1279-1281.
  • Hung, K. C., Huang, H.M. and Lin, P.W. (2015). “Changes of intraocular pressure and refractive status in children following cycloplegic refraction with 1% cyclopentolate and 1% tropicamide”, Taiwan Journal of. Ophthalmology, 5, 124-127.
  • Izake, E.L. (2007). “Chiral discrimination and enantioselective analysis of drugs: An overview“, Journal of Pharmaceutical Sciences, 96, 1659-1676.
  • Jamr’oz, M.H. (2004). Vibrational Energy Distribution Analysis VEDA4, Warsaw.
  • Lambert, J. B., Shurvell, H. F., and Cooks, R. G. (1987). Introduction to Organic Spectroscopy, Macmillan Publish, New York, USA.
  • Lee, C., Yang, W. and Parr, R.G. (1988). “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B, , 37, 785-789.
  • Li, T., Zhou, X., Chen, Z. and Zhou, X. (2015). “Effects of Cyclopentolate on Form Deprivation Myopia in Guinea Pigs”, Open Journal of Ophthalmology, 5, 10-18.
  • London, F. (1937). “Théorie quantique des courants interatomiques dans les combinaisons aromatiques”, J. Phys. Radium, 8, 397-409.
  • Mani, P., Umamaheswari, H., Joshua, B. D. and Sundaraganesan, N. (2008). “Molecular structure, vibrational spectra and NBO analysis of phenylisothiocyanate by density functional method”, Journal of Molecular Structure: THEOCHEM, 863, 44-49.
  • Mericko, D., Lehotay, J. and Cizmárik, J. (2007). “HPLC separation of enantiomers using chiral stationary phases”, Čes. slov. Farm, 56(3), 107-113.
  • Miertus, S., Scrocco, E. and Tomasi, J. (1981). “Electrostatic interaction of a solute with a continuum. Electrostatic interaction of a solute with a continuum. A direct utilization of AB initio molecular potentials for the prevision of solvent effects”, Chemical Physics, 55, 117-129.
  • Mindel, J. S. (1994). “Duane’s Foundations of Clinical Ophthalmology”, Vol. 3, JB Lippincott, Philadelphia.
  • O'boyle, M., Tenderholt, A. L. and Langner, K. M. (2008). “cclib: a library for package-independent computational chemistry algorithms”, Journal of Computational Chemistry, 29, 839-845.
  • Özer, A. (2005). “Görme Optiği ve Refraksiyon”, Tüm Optik ve Optometrik Meslekler Birliği Derneği.
  • Palafox, M. A. (2000). “Scaling Factors for the Prediction of Vibrational Spectra. I. Benzene Molecule”, International Journal of Quantum Chemistry, 77, 661-684.
  • Roeges, N. P. G. (1994). A Guide to the Complete Interpretation of Infrared Spectral of Organic Structures, John Wiley, Chichester.
  • Roy, A. K. and Guillory, J.K. (1995). “The kinetics and mechanism of the hydrolysis of cyclopentolate hydrochloride in alkaline solutions”, International Journal of Pharmaceutics, 120, 169-178.
  • Roy. A. K. and Guillory, J. K. (1996). “The effect of cyclodextrins on the aqueous stability of cyclopentolate hydrochloride”, International Journal of Pharmaceutics, 138, 37-43.
  • Runge, E. and Gross, E. K. U. (1984). “Gross, Density-functional theory for time-dependent systems”, Physical Review Letter, 52, 997-1000.
  • Russell D. Johnson III (Ed.). (2016). NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database, Number 101, Release 18, October, http://cccbdb.nist.gov/.
  • Sert, Y., Öztürk, N., Al-Omary, F. A. M., Alaşalvar, C., Al-Shehri, M. M., El-Emam, A. A. and Gökce, H. (2017). “Experimental (FT-IR, Laser-Raman and NMR) and theoretical spectroscopic analysis of 3-[(N-methylanilino) methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H) -thione”, Computational and Theoretical Chemistry, 16(3) 1750024.
  • Silverstein, R. M., Webster, F. X. and Kiemle, D. J. (2005). Spectroscopic Identification of Organic Compound, 7th ed., John Wiley & Sons, Inc., USA.
  • Sroczyński, D. and Malinowski, Z. (2017). “Spectroscopic investigations (FT-IR, UV, 1H and 13C NMR) and DFT/TD-DFT calculations of potential analgesic drug 2-[2-(dimethylamino)ethyl]-6-methoxy-4-(pyridin-2-yl)-1(2H)-phthalazinone”, Journal of Molecular Structure, 1150, 614-628.
  • Stuart, B. H. (2004). Infrared Spectroscopy: Fundamentals and Applications, JohnWilley & Sons, England.
  • Szwed, K., Gorecki, M. and Frelek, J. (2013). “Enantioselective extraction system containing binary chiral selectors and chromatographic enantioseparation method for determination of the absolute configuration of enantiomers of cyclopentolate”, Chromatographia, 76, 1603-1611.
  • Temel, E., Alaşalvar, C., Gökçe, H., Güder, A., Albayrak, Ç., Alpaslan, Y. B., Alpaslan, G. and Dilek, N. (2015). “DFT calculations, spectroscopy and antioxidant activity studies on (E)-2-nitro-4-[(phenylimino)methyl]phenol”, Spectrochimica Acta A, 136, 534-546.
  • Trotter, J. (1960). “Bond lengths in benzene derivatives: Hybridization or resonance”, Tetrahedron, 8, 13-22.
  • Vale, J. and Cox, B. (1978). “Drugs and the Eye”, Butterworth & Co (Publishers) Ltd.
  • Wolinski, K., Hinton, J.F. and Pulay, P. (1990). “Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations”, Journal of the American Chemical Society, 112, 8251-8260.

Structural, Spectroscopic (FT-IR, Raman, NMR and UV-Vis.) and Theoretical Investigations of Cyclopentolate

Yıl 2020, , 314 - 333, 20.03.2020
https://doi.org/10.18185/erzifbed.632227

Öz

In this study, the structural and
spectroscopic characterizations
(FT-IR, Laser-Raman, 1H
and
13C NMR and UV-vis spectra) of cyclopentolate were performed
using experimental and theoretical methods. Four conformational structures and
optimized molecular geometries of the molecule were examined. The vibrational
wavenumbers, proton and carbon-13 NMR chemical shifts, UV-Vis. parameters were
theoretically obtained for the most stable form of the molecule and the
HOMO-LUMO analyses were performed with DFT/B3LYP method at aug-cc-pVDZ basis
set. The weak intra-molecular hydrogen bond interaction in O45-H46…N23 group
was determined. The
1H and 13C NMR chemical shifts were
experimentally and theoretically investigated. The assignments of theoretical
vibrational modes were obtained using VEDA 4 software in terms of potential
energy distribution (PED). The theoretically and experimentally obtained data
were found to be consistent with each other. 

Kaynakça

  • Akyıldırım, O., Gökce, H., Bahçeli, S. and Yüksek, H. (2017). “Theoretical and spectroscopic (FT-IR, NMR and UV-Vis.) characterizations of 3-p-chlorobenzyl-4-(4-carboxybenzy lidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one molecule”, Journal of Molecular Structure, 1127, 114-123.
  • Ambujakshan, K. R., Madhavan, V.S., Varghese, H.T., Panicker, C. Y., Temiz-Arpaci, O., Tekiner-Gulbas B. and Yildiz I. (2008). “Vibrational spectroscopic studies and ab initio calculations of 5-methyl-2-(p-methylaminophenyl)benzoxazole, Spectrochim”. Spectrochimica Acta Part A, 69, 782-788.
  • Angelova, O., Macicek, J., Vassilev, N.G., Momchilova, S. and Petrova, J. (1992). “Structures of threo (RR,SS) diethyl ester of 2-hydroxy-1,2-diphenylethylphosphonic acid and (±)diethyl ester of (1-hydroxycyclopentyl)(2-methylphenyl) methylphosphonic acid”, J. Crystallogr. Spectrosc. Res., 22, 253-258.
  • Becke, A.D. (1993). “Density-functional thermochemistry. III. The role of exact Exchange”, J. Chem. Phys. 98, 5648-5652.
  • Bilkan, M. T. (2017). “Structural and spectroscopic studies on dimerization and solvent-ligand complexes of Theobromine”. Journal of Molecular Liquids, 238, 523–532.
  • Colthup, N.B., Daly, L.H. and Wiberley, E. (1964). Introduction to Infrared and Raman Spectroscopy, Academic Press, New York.
  • Dennington, R., Keith, T. and Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
  • Ditchfield, R. (1974). “Self-consistent perturbation theory of diamagnetism. I. A gauge-invariant LCAO method for N.M.R. chemical shifts”, Molecular Physics, 27, 789-807.
  • Farhood, Q. K. (2012). “Cycloplegic Refraction in Children with Cyclopentolate versus Atropine“, Journal of Clinical and Experimental Ophthalmol., 3(7), 1-5.
  • Frag, E. Y. Z., Mohamed, G.G., El-Dien F.A.N., and Mohamed, M. El-Badry. (2011). “The Use of Integrated Analytical Tools for Determination of Cyclopentolate and Naphazoline Hydrochlolrides in Pure and Pharmaceutical Preparations”, Pharmaceutica Analytica Acta, 2(1), 1-6.
  • Frisch, M.J. et al. (2009). Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT.
  • Fukui, K. (1982). “Role of frontier orbitals in chemical reactions”, Science, 218, 747-754.
  • H. Buyukuslu, M. Akdogan, G. Yildirim and C. Parlak. (2010). “Ab initio Hartree-Fock and density functional theory study on characterization of 3-(5-methylthiazol-2-yldiazenyl)-2-phenyl-1H-indole”, Spectrochim. Acta Part A, 75, 1362-1369.
  • H. Gökce and S. Bahçeli. (2013). “The molecular structures, vibrational spectroscopies (FT-IR and Raman) and quantum chemical calculations of n-alkyltrimethylammonium bromides”. Opt. Spectrosc, 115, 632-644.
  • Hirschler, J., Berger, B. and Bolte, M. (1994). “A dimeric (phenylsulfonyl) oxazolidine”, Acta Crystallographica, C50, 1279-1281.
  • Hung, K. C., Huang, H.M. and Lin, P.W. (2015). “Changes of intraocular pressure and refractive status in children following cycloplegic refraction with 1% cyclopentolate and 1% tropicamide”, Taiwan Journal of. Ophthalmology, 5, 124-127.
  • Izake, E.L. (2007). “Chiral discrimination and enantioselective analysis of drugs: An overview“, Journal of Pharmaceutical Sciences, 96, 1659-1676.
  • Jamr’oz, M.H. (2004). Vibrational Energy Distribution Analysis VEDA4, Warsaw.
  • Lambert, J. B., Shurvell, H. F., and Cooks, R. G. (1987). Introduction to Organic Spectroscopy, Macmillan Publish, New York, USA.
  • Lee, C., Yang, W. and Parr, R.G. (1988). “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B, , 37, 785-789.
  • Li, T., Zhou, X., Chen, Z. and Zhou, X. (2015). “Effects of Cyclopentolate on Form Deprivation Myopia in Guinea Pigs”, Open Journal of Ophthalmology, 5, 10-18.
  • London, F. (1937). “Théorie quantique des courants interatomiques dans les combinaisons aromatiques”, J. Phys. Radium, 8, 397-409.
  • Mani, P., Umamaheswari, H., Joshua, B. D. and Sundaraganesan, N. (2008). “Molecular structure, vibrational spectra and NBO analysis of phenylisothiocyanate by density functional method”, Journal of Molecular Structure: THEOCHEM, 863, 44-49.
  • Mericko, D., Lehotay, J. and Cizmárik, J. (2007). “HPLC separation of enantiomers using chiral stationary phases”, Čes. slov. Farm, 56(3), 107-113.
  • Miertus, S., Scrocco, E. and Tomasi, J. (1981). “Electrostatic interaction of a solute with a continuum. Electrostatic interaction of a solute with a continuum. A direct utilization of AB initio molecular potentials for the prevision of solvent effects”, Chemical Physics, 55, 117-129.
  • Mindel, J. S. (1994). “Duane’s Foundations of Clinical Ophthalmology”, Vol. 3, JB Lippincott, Philadelphia.
  • O'boyle, M., Tenderholt, A. L. and Langner, K. M. (2008). “cclib: a library for package-independent computational chemistry algorithms”, Journal of Computational Chemistry, 29, 839-845.
  • Özer, A. (2005). “Görme Optiği ve Refraksiyon”, Tüm Optik ve Optometrik Meslekler Birliği Derneği.
  • Palafox, M. A. (2000). “Scaling Factors for the Prediction of Vibrational Spectra. I. Benzene Molecule”, International Journal of Quantum Chemistry, 77, 661-684.
  • Roeges, N. P. G. (1994). A Guide to the Complete Interpretation of Infrared Spectral of Organic Structures, John Wiley, Chichester.
  • Roy, A. K. and Guillory, J.K. (1995). “The kinetics and mechanism of the hydrolysis of cyclopentolate hydrochloride in alkaline solutions”, International Journal of Pharmaceutics, 120, 169-178.
  • Roy. A. K. and Guillory, J. K. (1996). “The effect of cyclodextrins on the aqueous stability of cyclopentolate hydrochloride”, International Journal of Pharmaceutics, 138, 37-43.
  • Runge, E. and Gross, E. K. U. (1984). “Gross, Density-functional theory for time-dependent systems”, Physical Review Letter, 52, 997-1000.
  • Russell D. Johnson III (Ed.). (2016). NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database, Number 101, Release 18, October, http://cccbdb.nist.gov/.
  • Sert, Y., Öztürk, N., Al-Omary, F. A. M., Alaşalvar, C., Al-Shehri, M. M., El-Emam, A. A. and Gökce, H. (2017). “Experimental (FT-IR, Laser-Raman and NMR) and theoretical spectroscopic analysis of 3-[(N-methylanilino) methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H) -thione”, Computational and Theoretical Chemistry, 16(3) 1750024.
  • Silverstein, R. M., Webster, F. X. and Kiemle, D. J. (2005). Spectroscopic Identification of Organic Compound, 7th ed., John Wiley & Sons, Inc., USA.
  • Sroczyński, D. and Malinowski, Z. (2017). “Spectroscopic investigations (FT-IR, UV, 1H and 13C NMR) and DFT/TD-DFT calculations of potential analgesic drug 2-[2-(dimethylamino)ethyl]-6-methoxy-4-(pyridin-2-yl)-1(2H)-phthalazinone”, Journal of Molecular Structure, 1150, 614-628.
  • Stuart, B. H. (2004). Infrared Spectroscopy: Fundamentals and Applications, JohnWilley & Sons, England.
  • Szwed, K., Gorecki, M. and Frelek, J. (2013). “Enantioselective extraction system containing binary chiral selectors and chromatographic enantioseparation method for determination of the absolute configuration of enantiomers of cyclopentolate”, Chromatographia, 76, 1603-1611.
  • Temel, E., Alaşalvar, C., Gökçe, H., Güder, A., Albayrak, Ç., Alpaslan, Y. B., Alpaslan, G. and Dilek, N. (2015). “DFT calculations, spectroscopy and antioxidant activity studies on (E)-2-nitro-4-[(phenylimino)methyl]phenol”, Spectrochimica Acta A, 136, 534-546.
  • Trotter, J. (1960). “Bond lengths in benzene derivatives: Hybridization or resonance”, Tetrahedron, 8, 13-22.
  • Vale, J. and Cox, B. (1978). “Drugs and the Eye”, Butterworth & Co (Publishers) Ltd.
  • Wolinski, K., Hinton, J.F. and Pulay, P. (1990). “Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations”, Journal of the American Chemical Society, 112, 8251-8260.
Toplam 43 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Tuba Özdemir Öge 0000-0001-6690-7199

Halil Gökçe 0000-0003-2258-859X

Yayımlanma Tarihi 20 Mart 2020
Yayımlandığı Sayı Yıl 2020

Kaynak Göster

APA Özdemir Öge, T., & Gökçe, H. (2020). Structural, Spectroscopic (FT-IR, Raman, NMR and UV-Vis.) and Theoretical Investigations of Cyclopentolate. Erzincan University Journal of Science and Technology, 13(1), 314-333. https://doi.org/10.18185/erzifbed.632227