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Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods

Yıl 2019, Cilt: 9 Sayı: 1, 99 - 112, 28.06.2019

Halil Uğur Taşdemir Fatih Sevgi Ercan Türkkan

Öz

In this study, the conformational analysis was performed by the
semi-empirical PM3 method to determine the molecular structure of the glyoxime
molecule. Each of conformer  is optimized using
the Density Functionals Theory (DFT) with DFT / B3LYP / 6-311G ++ (d, p) method
basis set combination. As a result of the optimization, the most stable
structure was determined according to the energy order. The
chemical shift values ​​of 1H and 13C, which are Nuclear
Magnetic Resonance (NMR) parameters of this stable structure, were calculated
in liquid phase and gas phase using DFT method and six different basis sets. Furthermore, the effect of intermolecular
hydrogen bonding on 1H chemical shift values ​​was investigated by
dimer molecular modeling at the level of B3LYP / 6-31G ++ (d, p) in the DFT
method. The 1H and 13C chemical shift values ​​of the
glyoxime molecule were determined experimentally. Structural analyzes of the
glyoxime molecule were made by comparing the calculated NMR parameters with the
experimental NMR parameters.

Anahtar Kelimeler

Glyoxime Nuclear Magnetic Resonance Density Functional Theory Hydrogen Bonding

Kaynakça

  • Kaupp, M., Bühl, M., Malkin, V. G., Calculation of NMR and EPR parameters, Wiley-Vch, Weinheim, 2004.
  • Wu, A., Zhang, Y., Xu X., Yan, Y., Systematic Studies on the Computation of Nuclear Magnetic Resonance Shielding Constants and Chemical Shifts: The Density Functional Models, Journal of Computational Chemistry, 28 (15), 2431-2442, 2007.
  • Hehre, W. J., Radom, L., Schleyer, Pvon R., Pople, J. A., Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
  • Foresman, J. B., Frisch, A., Exploring Chemistry with Electronic Structure Methods, Gaussian, Pittsburgh, 1996.
  • Frisch, M. J., Frisch, A., Foresman, J. B., Gaussian 94 Users Reference, Gaussian, Pittsburgh, 1995.
  • Ruud, K., Helgaker, T., Kobayashi, R., Jorgensen, P., Bak, K. L., Jensen, H. J. A., Multiconfigurational self-consistent field calculations of nuclear shieldings using London atomic orbitals, Journal of Chemical Physics, 100 (11), 8178-8185, 1994.
  • Chesnut, D.B., Ab Initio Calculations of NMR Chemical Shielding, Annual, Reports on NMR Spectroscopy,29, 71-122, 1994.
  • de Dios, A.C., Ab initio calculations of the NMR chemical shift, Progress in Nuclear Magnetic Resonance Spectroscopy, 29 (3-4), 229-278, 1996
  • Barszczewicz, A., Jaszu´nski, M., Jackowski, K., Ab initio calculations of the oxygen atom NMR shielding in the carbonyl group, Chemical Physical Letters, 203 (4), 404-408, 1993.
  • Cheeseman, J.R., Trucks, G.W., Keith, T.A., Frisch, M.J., A comparison of models for calculating nuclear magnetic resonance shielding tensors, Journal of Chemical Physics, 104 (14), 5497-5509, 1996.
  • Kupka, T., Koaski, M., Pasterna, G., Ruud, K., Towards more reliable prediction of formaldehyde multinuclear NMR parameters and harmonic vibrations in the gas phase and solution, Journal of Molecular Structure ( THEOCHEM), 467 (1), 63-78, 1999.
  • DeHaven-Hudkins, D.L., Komer, K.M., Peterson, J.A., Mavunkel, B.J., Rzeszotarski, W.J., Opioid agonist properties of two oxime derivatives of naltrexone, NPC 831 and NPC 836, Pharmacology Biochemistry and Behavior, 44 (1), 45-50, 1993.
  • DeHaven-Hudkins, D.L., Brostrom, P.A., Allen, J.T., Lesko, L.J., Ferkany, J.W., Kaplita, P.V., Mavunkel, B.J., Rzeszotarski, W.J., Steranka, L.R., Pharmacologic Profile of NPC 168 (naltrexone phenyl oxime), A Novel Compound With Activity At Opioid Receptors, Pharmacology Biochemistry and Behavior, 37 (3), 497-504, 1990.
  • Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., D'Amico, M., Parrillo, C., Lampa, E., Rossi, F., N-Substituted 0-(3-amino-2- hydroxypropyl) Oximes of 1,3,3-trimethyl-5-endo-(1-piperidinyl or 4- morpholinyl)-2-oxabicyclo(2,2,2)-octan-6-ones With Platelet Antiaggregating and Local Anesthetic Activities, Farmaco, 47 (10), 1249-1262, 1992.
  • Ranise, A., Bondavalli, F., Bruno, O, Schenone, P,, Faillace, G., Coluccino, A., Filippelli, W., Di Sarno, A., Marmo, E., Omega-dialkylaminoalkyl Ethers of 3-EXO-dialkylamino-(z)-camphoroximes With Anitarrhythmic and Local Anesthetic Activities, Farmaco, 45 (2), 187-202, 1990.
  • Gasc, J.C., d'Ambrieres, S.G., Lutz, A., Chantot, J F., New Ether Oxime Derivates of Erythromycin A. A Structure-Activity Relationship Study, The Journal of Antibiotics (Tokyo), 44 (3), 313-330, 1991.
  • Cooper, C.S., Klock, P.L., Chu, D. T. W., Hardy, D. J., Swanson, R. N., Plattner, J. J., Preparation and in vitro and in vivo evaluation of quinolones with selective activity against Gram-positive organisms, Journal of Medicinal Chemistry, 35 (8), 1392-1398, 1992.
  • Tsukamoto, Y., Sato, K., Mio, S., Sugai, S., Yanai, T., Kitano, N., Muramatsu, S., Nakada, Y., Ide, J., Synthesis of 5-keto-5-oxime Derivates of Milbemycins and Their Activities Against Microfilariae, Agricultural and Biological Chemistry, 55 (10), 2615-2621, 1991.
  • Bowman, D.D., Darigrand, R.A., Frongillo, M.K., Barr, S.C., Flanders, J.A., Carbone, L.G., Treatment of experimentally induced trichinosis in dogs and cats, American Journal of Veterinary Research, 54 (8), 1303-1305, 1993.
  • Abdalla, S., Khalili, F., Effects of Dichloroglyoxime on Isolated Guinea-Pig Smooth Muscle and Atrium, Drug and Chemical Toxicology, 15 (2), 145-159, 1992.
  • Bodor, N., Elkoussi, A., Improved Delivery Through Biological Membranes.LVI.Pharmocological Evaluation of Alprenoxime-A New Potential Aniglaucoma Agent, Pharmaceutical Research, 8 (11), 1389-1395, 1991.
  • Ballantyne, B., Ophtalmic Effects of Oximes: A Review, Veterinary and Human Toxicology, 33 (2), 151-154, 1991.
  • Olofson, R., Michelman, J., Furuzan, Journal of Organic Chemistry, 30, 1854-1859, 1965.
  • Spartan 08 Programme, Wavefunction Inc., Irvine, CA 92612, USA, 2008.
  • Lee, C., Yang, W., Par,r R.G., Development of the Colle–Salvetti correlation- energy formula into a functional of the electron density, Physical Review B 37 (2), 785–789, 1988
  • Gaussian 03 Programme, Revision E.01, Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador,P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al- Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., 2003. Gaussian, Inc., Pittsburgh PA.
  • Taşdemir H.U., Calculation of NMR Parameters of Some Molecules Using HF, Post HF and DFT Methods Selçuk University, Master Thesis, Konya, 2010.
  • Jeffrey, G.A., Ruble, J.R., Pople, J.A., Neutron Diffraction at 9 K and ab initio Molecular Orbital Studies of the Molecular Structure of Glyoxime, Acta Crystallography, B38: 1975-1980, 1982.
  • Hori, S., Yamauchi, K., Kuroki, S., Ando, I., Proton NMR Chemical Shift Behavior of Hydrogen-Bonded Amide Proton of Glycine-Containing Peptides and Polypeptides as Studied by ab initio MO Calculation, International Journal of Molecular Sciences, 3 (8), 907-913, 2002.
  • Malek, K., Vala, M., Kozlowski, H., Proniewicz, L. M., Experimental and theoretical NMR study of selected oxocarboxylic acid oximes, Magnetic Resonance in Chemistry, 42 (1), 23-29, 2004.

Glioksim Molekülünün 1H ve 13C NMR Kimyasal Kayma Değerlerinin Deneysel ve Teorik Metotlar ile Belirlenmesi

Yıl 2019, Cilt: 9 Sayı: 1, 99 - 112, 28.06.2019

Halil Uğur Taşdemir Fatih Sevgi Ercan Türkkan

Öz

Bu çalışmada glioksim molekülünün moleküler yapısını belirlemek için konformasyon analizi yarı deneysel PM3 metodu ile yapılmıştır. Elde edilen konformasyonlar Yoğunluk Fonksiyonelleri Metodu (DFT) kullanılarak DFT/B3LYP/6-311G++(d,p) metot baz seti kombinasyonu ile optimize edilmiştir. Optimizasyon sonucunda enerji durumuna göre en kararlı yapı bulunmuştur. Bu kararlı yapıya ait Nükleer Manyetik Rezonans (NMR) parametreleri olan 1H ve 13C kimyasal kayma değerleri, DFT metodu ve 6 farklı baz seti kullanılarak sıvı fazda ve gaz fazında hesaplanmıştır. Ayrıca moleküller arası hidrojen bağının, 1H kimyasal kayma değerlerine etkisi DFT metodunda B3LYP/ 6-31G++(d,p) seviyesinde dimer moleküler modellemesi yapılarak incelenmiştir. Aynı zamanda glioksim molekülünün 1H ve 13C kimyasal kayma değerleri deneysel olarak da tespit edilmiştir. Hesaplanan NMR parametreleri ile deneysel NMR parametreleri karşılaştırılarak glioksim molekülünün yapı analizleri yapılmıştır.

Anahtar Kelimeler

Glioksim Nükleer manyetik rezonans Yoğunluk fonksiyonelleri teorisi Hidrojen bağı

Kaynakça

  • Kaupp, M., Bühl, M., Malkin, V. G., Calculation of NMR and EPR parameters, Wiley-Vch, Weinheim, 2004.
  • Wu, A., Zhang, Y., Xu X., Yan, Y., Systematic Studies on the Computation of Nuclear Magnetic Resonance Shielding Constants and Chemical Shifts: The Density Functional Models, Journal of Computational Chemistry, 28 (15), 2431-2442, 2007.
  • Hehre, W. J., Radom, L., Schleyer, Pvon R., Pople, J. A., Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
  • Foresman, J. B., Frisch, A., Exploring Chemistry with Electronic Structure Methods, Gaussian, Pittsburgh, 1996.
  • Frisch, M. J., Frisch, A., Foresman, J. B., Gaussian 94 Users Reference, Gaussian, Pittsburgh, 1995.
  • Ruud, K., Helgaker, T., Kobayashi, R., Jorgensen, P., Bak, K. L., Jensen, H. J. A., Multiconfigurational self-consistent field calculations of nuclear shieldings using London atomic orbitals, Journal of Chemical Physics, 100 (11), 8178-8185, 1994.
  • Chesnut, D.B., Ab Initio Calculations of NMR Chemical Shielding, Annual, Reports on NMR Spectroscopy,29, 71-122, 1994.
  • de Dios, A.C., Ab initio calculations of the NMR chemical shift, Progress in Nuclear Magnetic Resonance Spectroscopy, 29 (3-4), 229-278, 1996
  • Barszczewicz, A., Jaszu´nski, M., Jackowski, K., Ab initio calculations of the oxygen atom NMR shielding in the carbonyl group, Chemical Physical Letters, 203 (4), 404-408, 1993.
  • Cheeseman, J.R., Trucks, G.W., Keith, T.A., Frisch, M.J., A comparison of models for calculating nuclear magnetic resonance shielding tensors, Journal of Chemical Physics, 104 (14), 5497-5509, 1996.
  • Kupka, T., Koaski, M., Pasterna, G., Ruud, K., Towards more reliable prediction of formaldehyde multinuclear NMR parameters and harmonic vibrations in the gas phase and solution, Journal of Molecular Structure ( THEOCHEM), 467 (1), 63-78, 1999.
  • DeHaven-Hudkins, D.L., Komer, K.M., Peterson, J.A., Mavunkel, B.J., Rzeszotarski, W.J., Opioid agonist properties of two oxime derivatives of naltrexone, NPC 831 and NPC 836, Pharmacology Biochemistry and Behavior, 44 (1), 45-50, 1993.
  • DeHaven-Hudkins, D.L., Brostrom, P.A., Allen, J.T., Lesko, L.J., Ferkany, J.W., Kaplita, P.V., Mavunkel, B.J., Rzeszotarski, W.J., Steranka, L.R., Pharmacologic Profile of NPC 168 (naltrexone phenyl oxime), A Novel Compound With Activity At Opioid Receptors, Pharmacology Biochemistry and Behavior, 37 (3), 497-504, 1990.
  • Schenone, S., Bruno, O., Ranise, A., Bondavalli, F., D'Amico, M., Parrillo, C., Lampa, E., Rossi, F., N-Substituted 0-(3-amino-2- hydroxypropyl) Oximes of 1,3,3-trimethyl-5-endo-(1-piperidinyl or 4- morpholinyl)-2-oxabicyclo(2,2,2)-octan-6-ones With Platelet Antiaggregating and Local Anesthetic Activities, Farmaco, 47 (10), 1249-1262, 1992.
  • Ranise, A., Bondavalli, F., Bruno, O, Schenone, P,, Faillace, G., Coluccino, A., Filippelli, W., Di Sarno, A., Marmo, E., Omega-dialkylaminoalkyl Ethers of 3-EXO-dialkylamino-(z)-camphoroximes With Anitarrhythmic and Local Anesthetic Activities, Farmaco, 45 (2), 187-202, 1990.
  • Gasc, J.C., d'Ambrieres, S.G., Lutz, A., Chantot, J F., New Ether Oxime Derivates of Erythromycin A. A Structure-Activity Relationship Study, The Journal of Antibiotics (Tokyo), 44 (3), 313-330, 1991.
  • Cooper, C.S., Klock, P.L., Chu, D. T. W., Hardy, D. J., Swanson, R. N., Plattner, J. J., Preparation and in vitro and in vivo evaluation of quinolones with selective activity against Gram-positive organisms, Journal of Medicinal Chemistry, 35 (8), 1392-1398, 1992.
  • Tsukamoto, Y., Sato, K., Mio, S., Sugai, S., Yanai, T., Kitano, N., Muramatsu, S., Nakada, Y., Ide, J., Synthesis of 5-keto-5-oxime Derivates of Milbemycins and Their Activities Against Microfilariae, Agricultural and Biological Chemistry, 55 (10), 2615-2621, 1991.
  • Bowman, D.D., Darigrand, R.A., Frongillo, M.K., Barr, S.C., Flanders, J.A., Carbone, L.G., Treatment of experimentally induced trichinosis in dogs and cats, American Journal of Veterinary Research, 54 (8), 1303-1305, 1993.
  • Abdalla, S., Khalili, F., Effects of Dichloroglyoxime on Isolated Guinea-Pig Smooth Muscle and Atrium, Drug and Chemical Toxicology, 15 (2), 145-159, 1992.
  • Bodor, N., Elkoussi, A., Improved Delivery Through Biological Membranes.LVI.Pharmocological Evaluation of Alprenoxime-A New Potential Aniglaucoma Agent, Pharmaceutical Research, 8 (11), 1389-1395, 1991.
  • Ballantyne, B., Ophtalmic Effects of Oximes: A Review, Veterinary and Human Toxicology, 33 (2), 151-154, 1991.
  • Olofson, R., Michelman, J., Furuzan, Journal of Organic Chemistry, 30, 1854-1859, 1965.
  • Spartan 08 Programme, Wavefunction Inc., Irvine, CA 92612, USA, 2008.
  • Lee, C., Yang, W., Par,r R.G., Development of the Colle–Salvetti correlation- energy formula into a functional of the electron density, Physical Review B 37 (2), 785–789, 1988
  • Gaussian 03 Programme, Revision E.01, Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador,P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al- Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., 2003. Gaussian, Inc., Pittsburgh PA.
  • Taşdemir H.U., Calculation of NMR Parameters of Some Molecules Using HF, Post HF and DFT Methods Selçuk University, Master Thesis, Konya, 2010.
  • Jeffrey, G.A., Ruble, J.R., Pople, J.A., Neutron Diffraction at 9 K and ab initio Molecular Orbital Studies of the Molecular Structure of Glyoxime, Acta Crystallography, B38: 1975-1980, 1982.
  • Hori, S., Yamauchi, K., Kuroki, S., Ando, I., Proton NMR Chemical Shift Behavior of Hydrogen-Bonded Amide Proton of Glycine-Containing Peptides and Polypeptides as Studied by ab initio MO Calculation, International Journal of Molecular Sciences, 3 (8), 907-913, 2002.
  • Malek, K., Vala, M., Kozlowski, H., Proniewicz, L. M., Experimental and theoretical NMR study of selected oxocarboxylic acid oximes, Magnetic Resonance in Chemistry, 42 (1), 23-29, 2004.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Kimya
Yazarlar

Halil Uğur Taşdemir

Fatih Sevgi

Ercan Türkkan

Yayımlanma Tarihi 28 Haziran 2019
Gönderilme Tarihi 18 Ağustos 2018
Kabul Tarihi 31 Mayıs 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 9 Sayı: 1

Kaynak Göster

APA Taşdemir, H. U., Sevgi, F., & Türkkan, E. (2019). Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods. Adıyaman University Journal of Science, 9(1), 99-112.
AMA Taşdemir HU, Sevgi F, Türkkan E. Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods. ADYU J SCI. Haziran 2019;9(1):99-112.
Chicago Taşdemir, Halil Uğur, Fatih Sevgi, ve Ercan Türkkan. “Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule With Experimental and Theoretical Methods”. Adıyaman University Journal of Science 9, sy. 1 (Haziran 2019): 99-112.
EndNote Taşdemir HU, Sevgi F, Türkkan E (01 Haziran 2019) Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods. Adıyaman University Journal of Science 9 1 99–112.
IEEE H. U. Taşdemir, F. Sevgi, ve E. Türkkan, “Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods”, ADYU J SCI, c. 9, sy. 1, ss. 99–112, 2019.
ISNAD Taşdemir, Halil Uğur vd. “Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule With Experimental and Theoretical Methods”. Adıyaman University Journal of Science 9/1 (Haziran 2019), 99-112.
JAMA Taşdemir HU, Sevgi F, Türkkan E. Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods. ADYU J SCI. 2019;9:99–112.
MLA Taşdemir, Halil Uğur vd. “Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule With Experimental and Theoretical Methods”. Adıyaman University Journal of Science, c. 9, sy. 1, 2019, ss. 99-112.
Vancouver Taşdemir HU, Sevgi F, Türkkan E. Determination of 1H and 13C Nuclear Magnetic Resonance Chemical Shift Values of Glyoxime Molecule with Experimental and Theoretical Methods. ADYU J SCI. 2019;9(1):99-112.
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