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Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid

Year 2012, Volume: 25 Issue: 2, 343 - 354, 17.04.2012

Abstract

The theoretical conformational structure analyses were performed using density functional theory for thiol and thione tautomeric forms of thioacetic acid (TAA). At the B3LYP/6-311++G(d,p) level, thiol [CH3(C=O)SH] and thione [CH3(C=S)OH] were found more stable than anti forms and the energy differences between these two forms were computed to be ca. 6.7 kJ mol−1 and ca. 27 kJ mol−1, respectively. Barrier energies for thiol and thione forms of thioacetic acid were calculated by using the density functional theory [DFT(B3LYP)/6-311++G(d,p)] method contributing to more than 90% of the population in gas phase at room temperature and also reported a theoretical study on vibrational spectra of thiol and thione tautomeric forms of thioacetic acid obtained by the density functional theory.

 

 

                  Key Words: thioacetic acid, DFT calculations,

                  tautomerisation, PES, IR spectroscopy.

 

References

  • [1] Storer, A.C., Murphy, W.F., Carey, P.R., “The use of resonance Raman spectroscopy to monitor catalytically important bonds during enzymic catalysis. Application to the hydrolysis of methyl thionohippurate by papain”, J. Biol. Chem., 254: 3163-3165 (1979).
  • [2] Lowe, G., Williams, A., “Papain-catalysed hydrolysis of some hippuric esters. A new mechanism for papain-catalysed hydrolyses”, J. Biochem., 96: 199-204 (1965).
  • [3] Fausto, R., Batista de Carvalho, L.A.E., TeixeiraDias, J.J.C., “Molecular structure and properties of thioacetic acid”, J. Mol. Struct. (Theochem), 207: 67-83 (1990).
  • [4] Fausto, R., Batista de Carvalho, L.A.E., TeixeiraDias, J.J.C.; Ramos, M.N., “s-cis and s-trans Conformers of formic, thioformic and dithioformic acids. An ab initio study”, J. Chem. Soc. Faraday Trans 2. 85: 1945-1962 (1989).
  • [5] George, P., Bock, C.W., Schmiedekamp, A., “A comparative ab initio study of the geometry and force field of thionformic acid with formic and thiolformic acids”, J. Mol. Struct. (Theochem), 76: 363-374 (1981).
  • [6] Varughese, K.I., Storer, A.C., Carey, P.R., “Directional preference for a catalytically important nitrogen sulfur contact seen in acyl-thiolproteases”, J. Am. Chem. Soc., 106: 8252-8257 (1984).
  • [7] Huber, C.P., Carey, P.R., His, S.C., Lee, H.; Storer, A.C., “Conformational study of N-acyl amino acid esters and thiol esters by FT-IR and x-ray crystallography: evidence for a nitrogen sulfur interaction in thiol esters”, J. Am. Chem. Soc., 106: 8263-8268 (1984).
  • [8] Huber, C.P., Ozaki, Y., Pliura, D.H., Storer, A.C., Carey, P.R., “Precise structural information for transient enzyme-substrate complexes by a combined X-ray crystallographic-resonance Raman spectroscopic approach”, Biochemistry, 21: 3109- 3015 (1982).
  • [9] Fausto, R., Teixeira-Dias, J.J.C., Carey, P.R., “Elucidation of the conformational properties of Nformylglycine dithio acid by ab initio SCF-MO calculations”, J. Am. Chem. Soc., 113: 2471-2476 (1991).
  • [10] Fausto, R., Teixeira-Dias, J.J.C., “A comparative ab initio study of methyl formate, methyl thiolformate and methyl thionoformate“, J. Mol. Struct. (Theochem), 150: 381-389 (1987).
  • [11] Fausto, R.; Teixeira-Dias, J.J.C.; Carey, P.R., “Ab initio structural and conformational studies of HCSSH, CH3CSSH and HCSSCH3” J. Mol. Struct. (Theochem), 152: 119-135 (1987).
  • [12] Yaman (Özkütük), M., “Low Temperature Studies on Matrix Isolation IR Spectroscopy and Photochemistry of Biologically Active Dithiookzamide and Thioacetic Acid at Experimental and Theoretical”, Phd. Thesis. Eskişehir Osmangazi University, Eskişehir, 93, 107- 108 (2005).
  • [13] Fausto, R. (Ed.), Low Temperature Spectroscopy, NATO ASI Vol. 483, (1995).
  • [14] Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Matrix Photochemistry of CH3C(O)SX Molecules with X = H, CH3 , and C(O)CH3 : Formation of Ketene in Another Decomposition Channel of Sulfenyl Carbonyl Compounds”, J. Phys. Chem. A, 106: 7235-7244 (2002).
  • [15] Romano, R.M., Downs, A.J., “Matrix-Isolated van der Waals Complexes Formed between CO and Dihalogen Molecules, XY with X, Y = Cl, Br, or I” J. Phys. Chem. A., 107: 5298-5305 (2003).
  • [16] Erben M.F., Romano, R.M., Della, Ve´dova C.O., “Study of the Ionic Fragmentation of Shallow- and Core-Excited Fluorocarbonylsulfenyl Chloride, FC(O)SCl: Observation of a New Three-Body Dissociation Mechanism”, J. Phys. Chem. A, 108: 3938-3946 (2004).
  • [17] Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Matrix Photochemistry of the Chlorocarbonyl Sulfenyl Compounds ClC(O)SY, with Y = Cl or CH3”, J. Phys. Chem. A, 108: 7179-7187 (2004).
  • [18] Erben, M.F., Romano, R.M., Della Ve´dova, C.O., “Ionic Fragmentation on ClC(O)SCl. Evidence of a Highly Charged Molecular Ion and Confirmation of Unusual Dissociation Mechanisms for Halocarbonylsulfenyl Chlorides”, J. Phys. Chem. A, 109: 304-313 (2005).
  • [19] Erben, M.F., Gerone´s, M., Romano, R.M., Della Ve´dova, C.O., “Evidence of Site-Specific Fragmentation on Thioacetic Acid, CH3C(O)SH, Irradiated with Synchrotron Radiation around the S 2p and O 1s Regions”, J. Phys. Chem. A, 110: 875- 883 (2006).
  • [20] Tobo´n, Y.A., Nieto, L.I., Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Photochemical Reaction Channels of OCS with Cl2 , ICl, or IBr Isolated Together in an Argon Matrix: Isolation of syn-Iodocarbonylsulfenyl Bromide”, J. Phys. Chem. A, 110: 2674-2681 (2006).
  • [21] Romano, R.M., Picone, A.L., Downs, A.J., “MatrixIsolated van der Waals Complexes Formed between CS2 and Dihalogen Molecules XY, Where XY = Cl2 , Br2 , BrCl, ICl, or IBr”, J. Phys. Chem. A, 110: 12129-12135 (2006).
  • [22] Erben, M.F., Gerone´s, M., Romano, R.M., Della Ve´dova, C.O., “Dissociative Photoionization of Methoxycarbonylsulfenyl Chloride, CH3OC(O)SCl, Following Sulfur 2p, Chlorine 2p, and Oxygen 1s Excitations”, J. Phys. Chem. A, 111: 8062-8071 (2007).
  • [23] Gerone´s, M., Erben, M.F., Romano, R.M., Della Ve´dova, C.O., “He I Photoelectron Spectra and Valence Synchrotron Photoionization for XC(O)SCl (X = F, Cl) Compounds”, J. Phys. Chem. A, 112: 2228-2234 (2008).
  • [24] Gerone´s, M., Downs, A.J., Erben, M.F., Ge, M., Romano, R.M., Yao, L., Della Ve´dova, C.O., “HeI Photoelectron and Valence Synchrotron Photoionization Studies of the Thioester Molecule CH3C(O)SCH3
  • : Evidence of Vibronic Structure”, J. Phys. Chem. A, 112: 5947–5953 (2008).
  • [25] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., 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., Gonza´ lez, C., Pople, J. A. GAUSSIAN 03 Revision B. 04, Gaussian: Pittsburgh, PA, (2003).
  • [26] McLean, A.D., Chandler, G.S., “Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18”, J. Chem. Phys., 72: 5639-5648 (1980).
  • [27] Krishnan, R., Schlegel, H.B., Pople, J.A., “Derivative studies in configuration–interaction theory”, J. Chem. Phys., 72: 4654-4655 (1980).
  • [28] Becke, A.D., “Density-functional exchange-energy approximation with correct asymptotic behavior”, Phys. Rev. A., 38: 3098-3100 (1988).
  • [29] Lee, C., Yang, W., Parr, R.G., “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B., 37: 785-789 (1988).
  • [30] Vosko, S. H., Wilk, L., Nusair, M., “Accurate spindependent electron liquid correlation energies for local spin density calculations: a critical analysis”, Can. J. Phys., 58(8): 1200-1211 (1980).
  • [31] Frisch, M. J., Head-Gordon, M., Pople, J.A., “Semidirect algorithms for the MP2 energy and gradient“, Chem. Phys. Lett., 166: 281-289 (1990).
  • [32] Csaszar, P., Pulay, P., “Geometry optimization by direct inversion in the iterative subspace “, J. Mol. Struct., 114: 31-34 (1984).
  • [33] Peng, C., Schlegel, H., “Combining synchronous transit and quasi-Newton methods to find transition states“, Israel. J. Chem., 33: 449-454 (1993).
  • [34] Gordy, W., “A Relation Between Bond Force Constants, Bond Orders, Bond Lengths, and the Electronegativities of the Bonded Atoms”, J. Chem. Phys., 14: 305-320 (1946).
  • [35] Matsushita, T., Osamura, Y., Misawa, N., Nishimoto K., Tsuno, Y.,” An MO Study of Organic Sulfur Compounds. Comparison with the Corresponding Oxygen Compounds”, Bull. Chem. Soc. Jpn., 52: 2521-2526 (1979).
  • [36] Randhawa, H.S., Walter, W., Méese, C.O., “Vibrational and NMR spectra of light and heavy CH3COSH and CD3COSH in relation to tautomerism and hydrogen bonding“, J. Mol. Struct., 37: 187-192 (1977).
  • [37] Crowder, G.A., “The C-S Stretching Frequency in Thiol Acids and Esters”, Appl. Spectrosc., 26: 486- 487 (1972).
  • [38] Noe, E.A., “Dynamic nuclear magnetic resonance spectroscopy. Carbon-sulfur p-p .pi.-bonding and conformational equilibria in thioacetic acid“, J. Am. Chem. Soc., 99: 2803-2805 (1977)
Year 2012, Volume: 25 Issue: 2, 343 - 354, 17.04.2012

Abstract

References

  • [1] Storer, A.C., Murphy, W.F., Carey, P.R., “The use of resonance Raman spectroscopy to monitor catalytically important bonds during enzymic catalysis. Application to the hydrolysis of methyl thionohippurate by papain”, J. Biol. Chem., 254: 3163-3165 (1979).
  • [2] Lowe, G., Williams, A., “Papain-catalysed hydrolysis of some hippuric esters. A new mechanism for papain-catalysed hydrolyses”, J. Biochem., 96: 199-204 (1965).
  • [3] Fausto, R., Batista de Carvalho, L.A.E., TeixeiraDias, J.J.C., “Molecular structure and properties of thioacetic acid”, J. Mol. Struct. (Theochem), 207: 67-83 (1990).
  • [4] Fausto, R., Batista de Carvalho, L.A.E., TeixeiraDias, J.J.C.; Ramos, M.N., “s-cis and s-trans Conformers of formic, thioformic and dithioformic acids. An ab initio study”, J. Chem. Soc. Faraday Trans 2. 85: 1945-1962 (1989).
  • [5] George, P., Bock, C.W., Schmiedekamp, A., “A comparative ab initio study of the geometry and force field of thionformic acid with formic and thiolformic acids”, J. Mol. Struct. (Theochem), 76: 363-374 (1981).
  • [6] Varughese, K.I., Storer, A.C., Carey, P.R., “Directional preference for a catalytically important nitrogen sulfur contact seen in acyl-thiolproteases”, J. Am. Chem. Soc., 106: 8252-8257 (1984).
  • [7] Huber, C.P., Carey, P.R., His, S.C., Lee, H.; Storer, A.C., “Conformational study of N-acyl amino acid esters and thiol esters by FT-IR and x-ray crystallography: evidence for a nitrogen sulfur interaction in thiol esters”, J. Am. Chem. Soc., 106: 8263-8268 (1984).
  • [8] Huber, C.P., Ozaki, Y., Pliura, D.H., Storer, A.C., Carey, P.R., “Precise structural information for transient enzyme-substrate complexes by a combined X-ray crystallographic-resonance Raman spectroscopic approach”, Biochemistry, 21: 3109- 3015 (1982).
  • [9] Fausto, R., Teixeira-Dias, J.J.C., Carey, P.R., “Elucidation of the conformational properties of Nformylglycine dithio acid by ab initio SCF-MO calculations”, J. Am. Chem. Soc., 113: 2471-2476 (1991).
  • [10] Fausto, R., Teixeira-Dias, J.J.C., “A comparative ab initio study of methyl formate, methyl thiolformate and methyl thionoformate“, J. Mol. Struct. (Theochem), 150: 381-389 (1987).
  • [11] Fausto, R.; Teixeira-Dias, J.J.C.; Carey, P.R., “Ab initio structural and conformational studies of HCSSH, CH3CSSH and HCSSCH3” J. Mol. Struct. (Theochem), 152: 119-135 (1987).
  • [12] Yaman (Özkütük), M., “Low Temperature Studies on Matrix Isolation IR Spectroscopy and Photochemistry of Biologically Active Dithiookzamide and Thioacetic Acid at Experimental and Theoretical”, Phd. Thesis. Eskişehir Osmangazi University, Eskişehir, 93, 107- 108 (2005).
  • [13] Fausto, R. (Ed.), Low Temperature Spectroscopy, NATO ASI Vol. 483, (1995).
  • [14] Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Matrix Photochemistry of CH3C(O)SX Molecules with X = H, CH3 , and C(O)CH3 : Formation of Ketene in Another Decomposition Channel of Sulfenyl Carbonyl Compounds”, J. Phys. Chem. A, 106: 7235-7244 (2002).
  • [15] Romano, R.M., Downs, A.J., “Matrix-Isolated van der Waals Complexes Formed between CO and Dihalogen Molecules, XY with X, Y = Cl, Br, or I” J. Phys. Chem. A., 107: 5298-5305 (2003).
  • [16] Erben M.F., Romano, R.M., Della, Ve´dova C.O., “Study of the Ionic Fragmentation of Shallow- and Core-Excited Fluorocarbonylsulfenyl Chloride, FC(O)SCl: Observation of a New Three-Body Dissociation Mechanism”, J. Phys. Chem. A, 108: 3938-3946 (2004).
  • [17] Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Matrix Photochemistry of the Chlorocarbonyl Sulfenyl Compounds ClC(O)SY, with Y = Cl or CH3”, J. Phys. Chem. A, 108: 7179-7187 (2004).
  • [18] Erben, M.F., Romano, R.M., Della Ve´dova, C.O., “Ionic Fragmentation on ClC(O)SCl. Evidence of a Highly Charged Molecular Ion and Confirmation of Unusual Dissociation Mechanisms for Halocarbonylsulfenyl Chlorides”, J. Phys. Chem. A, 109: 304-313 (2005).
  • [19] Erben, M.F., Gerone´s, M., Romano, R.M., Della Ve´dova, C.O., “Evidence of Site-Specific Fragmentation on Thioacetic Acid, CH3C(O)SH, Irradiated with Synchrotron Radiation around the S 2p and O 1s Regions”, J. Phys. Chem. A, 110: 875- 883 (2006).
  • [20] Tobo´n, Y.A., Nieto, L.I., Romano, R.M., Della Ve´dova, C.O., Downs, A.J., “Photochemical Reaction Channels of OCS with Cl2 , ICl, or IBr Isolated Together in an Argon Matrix: Isolation of syn-Iodocarbonylsulfenyl Bromide”, J. Phys. Chem. A, 110: 2674-2681 (2006).
  • [21] Romano, R.M., Picone, A.L., Downs, A.J., “MatrixIsolated van der Waals Complexes Formed between CS2 and Dihalogen Molecules XY, Where XY = Cl2 , Br2 , BrCl, ICl, or IBr”, J. Phys. Chem. A, 110: 12129-12135 (2006).
  • [22] Erben, M.F., Gerone´s, M., Romano, R.M., Della Ve´dova, C.O., “Dissociative Photoionization of Methoxycarbonylsulfenyl Chloride, CH3OC(O)SCl, Following Sulfur 2p, Chlorine 2p, and Oxygen 1s Excitations”, J. Phys. Chem. A, 111: 8062-8071 (2007).
  • [23] Gerone´s, M., Erben, M.F., Romano, R.M., Della Ve´dova, C.O., “He I Photoelectron Spectra and Valence Synchrotron Photoionization for XC(O)SCl (X = F, Cl) Compounds”, J. Phys. Chem. A, 112: 2228-2234 (2008).
  • [24] Gerone´s, M., Downs, A.J., Erben, M.F., Ge, M., Romano, R.M., Yao, L., Della Ve´dova, C.O., “HeI Photoelectron and Valence Synchrotron Photoionization Studies of the Thioester Molecule CH3C(O)SCH3
  • : Evidence of Vibronic Structure”, J. Phys. Chem. A, 112: 5947–5953 (2008).
  • [25] Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., 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., Gonza´ lez, C., Pople, J. A. GAUSSIAN 03 Revision B. 04, Gaussian: Pittsburgh, PA, (2003).
  • [26] McLean, A.D., Chandler, G.S., “Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18”, J. Chem. Phys., 72: 5639-5648 (1980).
  • [27] Krishnan, R., Schlegel, H.B., Pople, J.A., “Derivative studies in configuration–interaction theory”, J. Chem. Phys., 72: 4654-4655 (1980).
  • [28] Becke, A.D., “Density-functional exchange-energy approximation with correct asymptotic behavior”, Phys. Rev. A., 38: 3098-3100 (1988).
  • [29] Lee, C., Yang, W., Parr, R.G., “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Phys. Rev. B., 37: 785-789 (1988).
  • [30] Vosko, S. H., Wilk, L., Nusair, M., “Accurate spindependent electron liquid correlation energies for local spin density calculations: a critical analysis”, Can. J. Phys., 58(8): 1200-1211 (1980).
  • [31] Frisch, M. J., Head-Gordon, M., Pople, J.A., “Semidirect algorithms for the MP2 energy and gradient“, Chem. Phys. Lett., 166: 281-289 (1990).
  • [32] Csaszar, P., Pulay, P., “Geometry optimization by direct inversion in the iterative subspace “, J. Mol. Struct., 114: 31-34 (1984).
  • [33] Peng, C., Schlegel, H., “Combining synchronous transit and quasi-Newton methods to find transition states“, Israel. J. Chem., 33: 449-454 (1993).
  • [34] Gordy, W., “A Relation Between Bond Force Constants, Bond Orders, Bond Lengths, and the Electronegativities of the Bonded Atoms”, J. Chem. Phys., 14: 305-320 (1946).
  • [35] Matsushita, T., Osamura, Y., Misawa, N., Nishimoto K., Tsuno, Y.,” An MO Study of Organic Sulfur Compounds. Comparison with the Corresponding Oxygen Compounds”, Bull. Chem. Soc. Jpn., 52: 2521-2526 (1979).
  • [36] Randhawa, H.S., Walter, W., Méese, C.O., “Vibrational and NMR spectra of light and heavy CH3COSH and CD3COSH in relation to tautomerism and hydrogen bonding“, J. Mol. Struct., 37: 187-192 (1977).
  • [37] Crowder, G.A., “The C-S Stretching Frequency in Thiol Acids and Esters”, Appl. Spectrosc., 26: 486- 487 (1972).
  • [38] Noe, E.A., “Dynamic nuclear magnetic resonance spectroscopy. Carbon-sulfur p-p .pi.-bonding and conformational equilibria in thioacetic acid“, J. Am. Chem. Soc., 99: 2803-2805 (1977)
There are 39 citations in total.

Details

Primary Language English
Journal Section Chemistry
Authors

Cemil Ogretır This is me

Müjgan Ozkutuk

Publication Date April 17, 2012
Published in Issue Year 2012 Volume: 25 Issue: 2

Cite

APA Ogretır, C., & Ozkutuk, M. (2012). Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid. Gazi University Journal of Science, 25(2), 343-354.
AMA Ogretır C, Ozkutuk M. Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid. Gazi University Journal of Science. April 2012;25(2):343-354.
Chicago Ogretır, Cemil, and Müjgan Ozkutuk. “Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid”. Gazi University Journal of Science 25, no. 2 (April 2012): 343-54.
EndNote Ogretır C, Ozkutuk M (April 1, 2012) Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid. Gazi University Journal of Science 25 2 343–354.
IEEE C. Ogretır and M. Ozkutuk, “Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid”, Gazi University Journal of Science, vol. 25, no. 2, pp. 343–354, 2012.
ISNAD Ogretır, Cemil - Ozkutuk, Müjgan. “Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid”. Gazi University Journal of Science 25/2 (April 2012), 343-354.
JAMA Ogretır C, Ozkutuk M. Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid. Gazi University Journal of Science. 2012;25:343–354.
MLA Ogretır, Cemil and Müjgan Ozkutuk. “Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid”. Gazi University Journal of Science, vol. 25, no. 2, 2012, pp. 343-54.
Vancouver Ogretır C, Ozkutuk M. Theoretical Conformational Studies of Thiol and Thione Forms of Thioacetic Acid. Gazi University Journal of Science. 2012;25(2):343-54.