Research Article
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ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID

Year 2022, Volume: 8 Issue: 2, 31 - 37, 30.12.2022

Sultan Kıncal , Cansu Topkaya , Ramazan Güp , Tuncer Hökelek

https://doi.org/10.22531/muglajsci.1099935

Abstract

C8H9N2O4 was prepared via acetylation of 1,3-dimethyl barbituric acid. The atomic and crystalline structures were determined using single crystal analysis (X-ray). It is a member of the monoclinic system P 21/c group of space with a = 8.6056 (3) Å, b = 9.1602 (3) Å, c = 11.9601 (4) Å, β = 109.410 (3)°, Z = 4 and V = 889.22 (5) Å3.

π–π interactions between circles of nearby molecules with intercentroid distances of 3.4300 (11) aid in the stability of the structure by keeping the crystals in place. The Hirshfeld surface (HS) analysis of the crystal structure reveals that the H... O/O... H (45.9%) and H... H (32.9%) interactions contribute the most to crystal packing. The most essential interactions in crystal packing are hydrogen bonding and van der Waals interactions. According to the dispersion, electrostatic and overall energy frameworks, the contribution of dispersion energy dominates the stability.

Keywords

Barbituric acid pyrimidine crystal structure energy framework interaction energy

Supporting Institution

Mugla Sıtkı Koçman University-Research Projects Coordination Office

Project Number

21/125/05/1

Thanks

This study work was supported by Muğla Sıtkı Koçman University Research Projects Coordination Office (grant number: 21/125/05/1). Thank You.

References

  • Gulliya, K. S. (1997). U.S. Patent No. 5,674,870. Washington, DC: U.S. Patent and Trademark Office.
  • Oliva, A., De Cillis, G., Grams, F., Livi, V., Zimmermann, G., Menta, E., & Krell, H. W. (2002). U.S. Patent No. 6,335,332. Washington, DC: U.S. Patent and Trademark Office.
  • Rastaldo, R., Penna, C. and Pagliaro, P., ‘’Comparison between the effects of pentobarbital or ketamine/nitrous oxide anesthesia on metabolic and endothelial components of coronary reactive hyperemia’’, Life Sciences, 69(6), 729-738, 2001.
  • Aiken, S. P. and Brown, W. M., ‘’Treatment of epilepsy: existing therapies and future developments’’, Front Biosci, 5(1), E124-52, 2000.
  • Ghansah, E. and Weiss, D. S., ‘’ Modulation of GABAA receptors by benzodiazepines and barbiturates is autonomous of PKC activation’’, Neuropharmacology, 40(3), 327-333, 2001.
  • Ma, L., Li, S., Zheng, H., Chen, J., Lin, L., Ye, X. and Chen, L., ‘’Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease’’, European journal of medicinal chemistry, 46(6), 2003-2010, 2011.
  • Laxmi, S. V., Janardhan, B., Rajitha, B., Raghavaiah, P. and Srinivas, P., ‘’Synthesis, single crystal X-ray studies and antimicrobial activities of novel Indole barbiturates’’, Medicinal Chemistry Research, 21(10), 2896-2901, 2012.
  • Palwinder, S., Matinder, K. and Pooja, V., ‘’Design, synthesis and anticancer activities of hybrids of indole and barbituric acids—Identification of highly promising leads’’, Bioorg Med Chem Lett, 19, 3054-3058, 2009.
  • Shiradkar, M. R., Ghodake, M., Bothara, K. G., Bhandari, S. V., Nikalje, A., Akula, K. C. and Burange, P. J., ‘’Synthesis and anticonvulsant activity of clubbed thiazolidinone–barbituric acid and thiazolidinone–triazole derivatives’’, Arkivoc, 14, 58-74, 2007.
  • Goodman, L.S, Gilman, A., The pharmacological basis of therapeutics, The Macmillan,1975.
  • Giziroglu, E., Aygün, M., Sarikurkcu, C., Kazar, D., Orhan, N., Firinci, E. and Gokcen, C., ‘’Synthesis, characterization and antioxidant activity of new dibasic tridentate ligands: X-ray crystal structures of DMSO adducts of 1, 3-dimethyl-5-acetyl-barbituric acid o-hydroxybenzoyl hydrazone copper (II) complex’’, Inorganic Chemistry Communications, 36, 199-205, 2013.
  • Jursic, B. S. and Neumann, D. M., ‘’Preparation of 5-formyl-and 5-acetylbarbituric acids, including the corresponding Schiff bases and phenylhydrazones’’, Tetrahedron Letters, 42(48), 8435-8439,2001.
  • Gup, R. and Giziroğlu, E., ‘’Metal complexes and solvent extraction properties of isonitrosoacetophenone 2-aminobenzoylhydrazone’’, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 65(3-4), 719-726, 2006.
  • Kaminsky, W., Jasinski, J. P., Woudenberg, R., Goldberg, K. I. and West, D. X., ‘’Structural study of two N (4)-substituted thiosemicarbazones prepared from 1-phenyl-1, 2-propanedione-2-oxime and their binuclear nickel (II) complexes’’, Journal of molecular structure, 608(2-3), 135-141, 2002.
  • Bertrand, J. A., Smith, J. H. and Eller, P. G. ‘’Crystal and molecular structure of bis {perchlorato [2-(2-hydroxyethyl) imino-3-oximobutanato] aquocopper (II)}. Copper (II) dimer with bridging oxime groups’’, Inorganic Chemistry, 13(7), 1649-1653,1974.
  • Butcher, R. J., O'Connor, C. J. and Sinn, E., ‘’Synthesis and relation between magnetism and structure of the binuclear copper (II) oxime complex [Cu2L2 (ClO4) 2].[Cu2L2 (CH3OH) 2](ClO4) 2, where HL= 1-(N, N-dimethyl-2-aminoethylimino)-1-phenyl-2-oximopropane’’, Inorganic Chemistry, 18(7), 1913-1918, 1979.
  • Abraham, F., Capon, J. M., Nowogrocki, G., Sueur, S. and Bremard, C., ‘’Synthesis, X-ray structure and spectroscopy of Cu (II) complexes derived from diacetylazine dioxime’’, Polyhedron, 4(10), 1761-1767,1985.
  • Maekawa, M., Kitagawa, S., Nakao, Y., Sakamoto, S., Yatani, A., Mori, W. and Munakata, M., ‘’Syntheses, crystal structures and autoreduction behavior of antiferromagnetically coupled dicopper (II) oximato complexes’’, Inorganica chimica acta, 293(1), 20-29, 1999.
  • Wan, S. P., Mori, W. and Yamada, S., ‘’Synthesis and properties of iodinated nickel imineoximes’’, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 16(9), 1273-1288, 1986.
  • A Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. and Almajan, G. L., ‘’New Cu (II), Co (II), Ni (II) complexes with aroyl-hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation’’, European journal of medicinal chemistry, 45(5), 2055-2062, 2010.
  • Savini, L., Chiasserini, L., Gaeta, A. and Pellerano, C., ‘’Synthesis and anti-tubercular evaluation of 4-quinolylhydrazones’’, Bioorganic & medicinal chemistry, 10(7), 2193-2198,2002.
  • Giziroglua, E., Sarikurkcub, C. and Saracc, N., ‘’Synthesis and characterization of novel Hydrazone based anti-mutagenic and Antioxidative agents’’, Journal of Applied Pharmaceutical Science, 5(3), 048-055, 2015.
  • A Chugunova, E., D Voloshina, A., E Mukhamatdinova, R., V Serkov, I., N Proshin, A., M Gibadullina, E. and Goumont, R., ‘’ The study of the biological activity of amino-substituted benzofuroxans’’, Letters in Drug Design & Discovery, 11(4), 502-512, 2014.
  • Glinma, B., Gbaguıdı, F. A., Urbain, C. K., Kpovıessı, S. D., Houngbeme, A., Houngue, H. D. And Poupaert, J. H., ‘’Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis’’, Journal of Applied Pharmaceutical Science, 5(06), 001-007, 2015.
  • Mahmudov, K. T., Kopylovich, M. N., Maharramov, A. M., Kurbanova, M. M., Gurbanov, A. V. and Pombeiro, A. J., ‘’Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds’’, Coordination Chemistry Reviews, 265, 1-37, 2014.
  • Bojarski, J. T., Mokrosz, J. L., Bartoń, H. J. and Paluchowska, M. H., ‘’Recent progress in barbituric acid chemistry’’, Advances in heterocyclic chemistry, 38, 229-297,1985.
  • Patrick, G. L., An introduction to medicinal chemistry, Oxford university press.,2013.
  • Parvathy, K. S., Negi, P. S. and Srinivas, P., ‘’Curcumin–amino acid conjugates: synthesis, antioxidant and antimutagenic attributes’’, Food Chemistry, 120(2), 523-530, 2010.
  • Abele, E., Abele, R., Golomba, L., Višņevska, J., Beresneva, T., Rubina, K. and Lukevics, E., ‘’Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity’’, Chemistry of heterocyclic compounds, 46(8), 905-930,2010.
  • Neumann, D. M., Cammarata, A., Backes, G., Palmer, G. E. and Jursic, B. S., ‘’Synthesis and antifungal activity of substituted 2, 4, 6-pyrimidinetrione carbaldehyde hydrazones’’, Bioorganic & medicinal chemistry, 22(2), 813-826,2014.
  • Zheng, L. W., Li, Y., Ge, D., Zhao, B. X., Liu, Y. R., Lv, H. S. and Miao, J. Y., ‘’Synthesis of novel oxime-containing pyrazole derivatives and discovery of regulators for apoptosis and autophagy in A549 lung cancer cells’’ Bioorganic & medicinal chemistry letters, 20(16), 4766-4770, 2010.
  • Dörwald, F. Z., Lead optimization for medicinal chemists: pharmacokinetic properties of functional groups and organic compounds. John Wiley & Sons, 2012.
  • Khan, K. M., Khan, M., Ali, M., Taha, M., Hameed, A., Ali, S. and Choudhary, M. I., ‘’Synthesis and DPPH radical scavenging activity of 5-arylidene-N, N-dimethylbarbiturates’’, Medicinal Chemistry (Shariqah (United Arab Emirates)), 7(3), 231-236, 2011.
  • Sheldrick, G. M., ‘’A short history of SHELX’’, Acta Crystallographica Section A: Foundations of Crystallography, 64(1), 112-122, 2008.
  • Farrugia, L. J., ‘’WinGX and ORTEP for Windows: an update’’, Journal of Applied Crystallography, 45(4), 849-854, 2012.
  • Gup, R., Giziroglu, E. and Kırkan, B., ‘’Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline’’, Dyes and pigments, 73(1), 40-46, 2007.
  • Kirkan, B. and Gup, R., ‘’Synthesis of new azo dyes and copper (II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone’’, Turkish Journal of Chemistry, 32(1), 9-17, 2008.
  • Neumann, D. M., Cammarata, A., Backes, G., Palmer, G. E. and Jursic, B. S., ‘’Synthesis and antifungal activity of substituted 2, 4, 6-pyrimidinetrione carbaldehyde hydrazones’’, Bioorganic & medicinal chemistry, 22(2), 813-826, 2014.
  • Bruker, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2012.
  • Spek, A. L., ‘’checkCIF validation ALERTS: what they mean and how to respond’’, Acta Crystallographica Section E: Crystallographic Communications, 76(1), 1-11., 2020.
  • Hirshfeld, F. L., ‘’Bonded-atom fragments for describing molecular charge densities’’ Theoretica chimica acta, 44(2), 129-138, 1977.
  • Spackman, M. A. and Jayatilaka, D., ‘’Hirshfeld surface analysis’’, CrystEngComm, 11(1), 19-32, 2009.
  • Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. and Spackman, M. A., CrystalExplorer17. The University of Western Australia, 2017.
  • Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H. and Sundius, T., ‘’Crystal structure, Hirshfeld surfaces and DFT computation of NLO active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl) amino] prop-2-enoic acid’’, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 153, 625-636, 2016.
  • Spackman, M. A., McKinnon, J. J. and Jayatilaka, D., ‘’Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals’’, CrystEngComm, 10(4), 377-388, 2008.
  • Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylor, C., Wolff, S. K., Cassam-Chenai, P. and Whitton, A., TONTO - A System for Computational Chemistry. Available at: http://hirshfeldsurface.net/, 2005.
  • McKinnon, J. J., Jayatilaka, D. and Spackman, M. A., ‘’Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces’’ Chemical Communications, (37), 3814-3816, 2007.
  • Hathwar, V. R., Sist, M., Jørgensen, M. R., Mamakhel, A. H., Wang, X., Hoffmann, C. M. and Iversen, B. B., ‘’Quantitative analysis of intermolecular interactions in orthorhombic rubrene’’, IUCrJ, 2(5), 563-574., 2015.
  • Turner, M. J., Grabowsky, S., Jayatilaka, D. and Spackman, M. A., ‘’Accurate and efficient model energies for exploring intermolecular interactions in molecular crystals’’ The journal of physical chemistry letters, 5(24), 4249-4255, 2014.
  • Turner, M. J., Thomas, S. P., Shi, M. W., Jayatilaka, D. and Spackman, M. A., ‘’Energy frameworks: insights into interaction anisotropy and the mechanical properties of molecular crystals’’, Chemical Communications, 51(18), 3735-3738, 2015.
  • Mackenzie, C. F., Spackman, P. R., Jayatilaka, D. and Spackman, M. A., ‘’CrystalExplorer model energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems’’, IUCrJ, 4(5), 575-587, 2017.

Year 2022, Volume: 8 Issue: 2, 31 - 37, 30.12.2022

Sultan Kıncal , Cansu Topkaya , Ramazan Güp , Tuncer Hökelek

https://doi.org/10.22531/muglajsci.1099935

Abstract

Project Number

21/125/05/1

References

  • Gulliya, K. S. (1997). U.S. Patent No. 5,674,870. Washington, DC: U.S. Patent and Trademark Office.
  • Oliva, A., De Cillis, G., Grams, F., Livi, V., Zimmermann, G., Menta, E., & Krell, H. W. (2002). U.S. Patent No. 6,335,332. Washington, DC: U.S. Patent and Trademark Office.
  • Rastaldo, R., Penna, C. and Pagliaro, P., ‘’Comparison between the effects of pentobarbital or ketamine/nitrous oxide anesthesia on metabolic and endothelial components of coronary reactive hyperemia’’, Life Sciences, 69(6), 729-738, 2001.
  • Aiken, S. P. and Brown, W. M., ‘’Treatment of epilepsy: existing therapies and future developments’’, Front Biosci, 5(1), E124-52, 2000.
  • Ghansah, E. and Weiss, D. S., ‘’ Modulation of GABAA receptors by benzodiazepines and barbiturates is autonomous of PKC activation’’, Neuropharmacology, 40(3), 327-333, 2001.
  • Ma, L., Li, S., Zheng, H., Chen, J., Lin, L., Ye, X. and Chen, L., ‘’Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease’’, European journal of medicinal chemistry, 46(6), 2003-2010, 2011.
  • Laxmi, S. V., Janardhan, B., Rajitha, B., Raghavaiah, P. and Srinivas, P., ‘’Synthesis, single crystal X-ray studies and antimicrobial activities of novel Indole barbiturates’’, Medicinal Chemistry Research, 21(10), 2896-2901, 2012.
  • Palwinder, S., Matinder, K. and Pooja, V., ‘’Design, synthesis and anticancer activities of hybrids of indole and barbituric acids—Identification of highly promising leads’’, Bioorg Med Chem Lett, 19, 3054-3058, 2009.
  • Shiradkar, M. R., Ghodake, M., Bothara, K. G., Bhandari, S. V., Nikalje, A., Akula, K. C. and Burange, P. J., ‘’Synthesis and anticonvulsant activity of clubbed thiazolidinone–barbituric acid and thiazolidinone–triazole derivatives’’, Arkivoc, 14, 58-74, 2007.
  • Goodman, L.S, Gilman, A., The pharmacological basis of therapeutics, The Macmillan,1975.
  • Giziroglu, E., Aygün, M., Sarikurkcu, C., Kazar, D., Orhan, N., Firinci, E. and Gokcen, C., ‘’Synthesis, characterization and antioxidant activity of new dibasic tridentate ligands: X-ray crystal structures of DMSO adducts of 1, 3-dimethyl-5-acetyl-barbituric acid o-hydroxybenzoyl hydrazone copper (II) complex’’, Inorganic Chemistry Communications, 36, 199-205, 2013.
  • Jursic, B. S. and Neumann, D. M., ‘’Preparation of 5-formyl-and 5-acetylbarbituric acids, including the corresponding Schiff bases and phenylhydrazones’’, Tetrahedron Letters, 42(48), 8435-8439,2001.
  • Gup, R. and Giziroğlu, E., ‘’Metal complexes and solvent extraction properties of isonitrosoacetophenone 2-aminobenzoylhydrazone’’, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 65(3-4), 719-726, 2006.
  • Kaminsky, W., Jasinski, J. P., Woudenberg, R., Goldberg, K. I. and West, D. X., ‘’Structural study of two N (4)-substituted thiosemicarbazones prepared from 1-phenyl-1, 2-propanedione-2-oxime and their binuclear nickel (II) complexes’’, Journal of molecular structure, 608(2-3), 135-141, 2002.
  • Bertrand, J. A., Smith, J. H. and Eller, P. G. ‘’Crystal and molecular structure of bis {perchlorato [2-(2-hydroxyethyl) imino-3-oximobutanato] aquocopper (II)}. Copper (II) dimer with bridging oxime groups’’, Inorganic Chemistry, 13(7), 1649-1653,1974.
  • Butcher, R. J., O'Connor, C. J. and Sinn, E., ‘’Synthesis and relation between magnetism and structure of the binuclear copper (II) oxime complex [Cu2L2 (ClO4) 2].[Cu2L2 (CH3OH) 2](ClO4) 2, where HL= 1-(N, N-dimethyl-2-aminoethylimino)-1-phenyl-2-oximopropane’’, Inorganic Chemistry, 18(7), 1913-1918, 1979.
  • Abraham, F., Capon, J. M., Nowogrocki, G., Sueur, S. and Bremard, C., ‘’Synthesis, X-ray structure and spectroscopy of Cu (II) complexes derived from diacetylazine dioxime’’, Polyhedron, 4(10), 1761-1767,1985.
  • Maekawa, M., Kitagawa, S., Nakao, Y., Sakamoto, S., Yatani, A., Mori, W. and Munakata, M., ‘’Syntheses, crystal structures and autoreduction behavior of antiferromagnetically coupled dicopper (II) oximato complexes’’, Inorganica chimica acta, 293(1), 20-29, 1999.
  • Wan, S. P., Mori, W. and Yamada, S., ‘’Synthesis and properties of iodinated nickel imineoximes’’, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 16(9), 1273-1288, 1986.
  • A Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. and Almajan, G. L., ‘’New Cu (II), Co (II), Ni (II) complexes with aroyl-hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation’’, European journal of medicinal chemistry, 45(5), 2055-2062, 2010.
  • Savini, L., Chiasserini, L., Gaeta, A. and Pellerano, C., ‘’Synthesis and anti-tubercular evaluation of 4-quinolylhydrazones’’, Bioorganic & medicinal chemistry, 10(7), 2193-2198,2002.
  • Giziroglua, E., Sarikurkcub, C. and Saracc, N., ‘’Synthesis and characterization of novel Hydrazone based anti-mutagenic and Antioxidative agents’’, Journal of Applied Pharmaceutical Science, 5(3), 048-055, 2015.
  • A Chugunova, E., D Voloshina, A., E Mukhamatdinova, R., V Serkov, I., N Proshin, A., M Gibadullina, E. and Goumont, R., ‘’ The study of the biological activity of amino-substituted benzofuroxans’’, Letters in Drug Design & Discovery, 11(4), 502-512, 2014.
  • Glinma, B., Gbaguıdı, F. A., Urbain, C. K., Kpovıessı, S. D., Houngbeme, A., Houngue, H. D. And Poupaert, J. H., ‘’Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis’’, Journal of Applied Pharmaceutical Science, 5(06), 001-007, 2015.
  • Mahmudov, K. T., Kopylovich, M. N., Maharramov, A. M., Kurbanova, M. M., Gurbanov, A. V. and Pombeiro, A. J., ‘’Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds’’, Coordination Chemistry Reviews, 265, 1-37, 2014.
  • Bojarski, J. T., Mokrosz, J. L., Bartoń, H. J. and Paluchowska, M. H., ‘’Recent progress in barbituric acid chemistry’’, Advances in heterocyclic chemistry, 38, 229-297,1985.
  • Patrick, G. L., An introduction to medicinal chemistry, Oxford university press.,2013.
  • Parvathy, K. S., Negi, P. S. and Srinivas, P., ‘’Curcumin–amino acid conjugates: synthesis, antioxidant and antimutagenic attributes’’, Food Chemistry, 120(2), 523-530, 2010.
  • Abele, E., Abele, R., Golomba, L., Višņevska, J., Beresneva, T., Rubina, K. and Lukevics, E., ‘’Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity’’, Chemistry of heterocyclic compounds, 46(8), 905-930,2010.
  • Neumann, D. M., Cammarata, A., Backes, G., Palmer, G. E. and Jursic, B. S., ‘’Synthesis and antifungal activity of substituted 2, 4, 6-pyrimidinetrione carbaldehyde hydrazones’’, Bioorganic & medicinal chemistry, 22(2), 813-826,2014.
  • Zheng, L. W., Li, Y., Ge, D., Zhao, B. X., Liu, Y. R., Lv, H. S. and Miao, J. Y., ‘’Synthesis of novel oxime-containing pyrazole derivatives and discovery of regulators for apoptosis and autophagy in A549 lung cancer cells’’ Bioorganic & medicinal chemistry letters, 20(16), 4766-4770, 2010.
  • Dörwald, F. Z., Lead optimization for medicinal chemists: pharmacokinetic properties of functional groups and organic compounds. John Wiley & Sons, 2012.
  • Khan, K. M., Khan, M., Ali, M., Taha, M., Hameed, A., Ali, S. and Choudhary, M. I., ‘’Synthesis and DPPH radical scavenging activity of 5-arylidene-N, N-dimethylbarbiturates’’, Medicinal Chemistry (Shariqah (United Arab Emirates)), 7(3), 231-236, 2011.
  • Sheldrick, G. M., ‘’A short history of SHELX’’, Acta Crystallographica Section A: Foundations of Crystallography, 64(1), 112-122, 2008.
  • Farrugia, L. J., ‘’WinGX and ORTEP for Windows: an update’’, Journal of Applied Crystallography, 45(4), 849-854, 2012.
  • Gup, R., Giziroglu, E. and Kırkan, B., ‘’Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline’’, Dyes and pigments, 73(1), 40-46, 2007.
  • Kirkan, B. and Gup, R., ‘’Synthesis of new azo dyes and copper (II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone’’, Turkish Journal of Chemistry, 32(1), 9-17, 2008.
  • Neumann, D. M., Cammarata, A., Backes, G., Palmer, G. E. and Jursic, B. S., ‘’Synthesis and antifungal activity of substituted 2, 4, 6-pyrimidinetrione carbaldehyde hydrazones’’, Bioorganic & medicinal chemistry, 22(2), 813-826, 2014.
  • Bruker, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA, 2012.
  • Spek, A. L., ‘’checkCIF validation ALERTS: what they mean and how to respond’’, Acta Crystallographica Section E: Crystallographic Communications, 76(1), 1-11., 2020.
  • Hirshfeld, F. L., ‘’Bonded-atom fragments for describing molecular charge densities’’ Theoretica chimica acta, 44(2), 129-138, 1977.
  • Spackman, M. A. and Jayatilaka, D., ‘’Hirshfeld surface analysis’’, CrystEngComm, 11(1), 19-32, 2009.
  • Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. and Spackman, M. A., CrystalExplorer17. The University of Western Australia, 2017.
  • Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H. and Sundius, T., ‘’Crystal structure, Hirshfeld surfaces and DFT computation of NLO active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl) amino] prop-2-enoic acid’’, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 153, 625-636, 2016.
  • Spackman, M. A., McKinnon, J. J. and Jayatilaka, D., ‘’Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals’’, CrystEngComm, 10(4), 377-388, 2008.
  • Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylor, C., Wolff, S. K., Cassam-Chenai, P. and Whitton, A., TONTO - A System for Computational Chemistry. Available at: http://hirshfeldsurface.net/, 2005.
  • McKinnon, J. J., Jayatilaka, D. and Spackman, M. A., ‘’Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces’’ Chemical Communications, (37), 3814-3816, 2007.
  • Hathwar, V. R., Sist, M., Jørgensen, M. R., Mamakhel, A. H., Wang, X., Hoffmann, C. M. and Iversen, B. B., ‘’Quantitative analysis of intermolecular interactions in orthorhombic rubrene’’, IUCrJ, 2(5), 563-574., 2015.
  • Turner, M. J., Grabowsky, S., Jayatilaka, D. and Spackman, M. A., ‘’Accurate and efficient model energies for exploring intermolecular interactions in molecular crystals’’ The journal of physical chemistry letters, 5(24), 4249-4255, 2014.
  • Turner, M. J., Thomas, S. P., Shi, M. W., Jayatilaka, D. and Spackman, M. A., ‘’Energy frameworks: insights into interaction anisotropy and the mechanical properties of molecular crystals’’, Chemical Communications, 51(18), 3735-3738, 2015.
  • Mackenzie, C. F., Spackman, P. R., Jayatilaka, D. and Spackman, M. A., ‘’CrystalExplorer model energies and energy frameworks: extension to metal coordination compounds, organic salts, solvates and open-shell systems’’, IUCrJ, 4(5), 575-587, 2017.
There are 51 citations in total.

Details

Primary Language English
Journal Section Journals
Authors

Sultan Kıncal 0000-0003-3865-9671

Cansu Topkaya 0000-0002-6834-4841

Ramazan Güp 0000-0001-5731-6733

Tuncer Hökelek 0000-0002-8602-4382

Project Number 21/125/05/1
Early Pub Date November 2, 2022
Publication Date December 30, 2022
Published in Issue Year 2022 Volume: 8 Issue: 2

Cite

APA Kıncal, S., Topkaya, C., Güp, R., Hökelek, T. (2022). ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID. Mugla Journal of Science and Technology, 8(2), 31-37. https://doi.org/10.22531/muglajsci.1099935
AMA Kıncal S, Topkaya C, Güp R, Hökelek T. ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID. MJST. December 2022;8(2):31-37. doi:10.22531/muglajsci.1099935
Chicago Kıncal, Sultan, Cansu Topkaya, Ramazan Güp, and Tuncer Hökelek. “ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID”. Mugla Journal of Science and Technology 8, no. 2 (December 2022): 31-37. https://doi.org/10.22531/muglajsci.1099935.
EndNote Kıncal S, Topkaya C, Güp R, Hökelek T (December 1, 2022) ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID. Mugla Journal of Science and Technology 8 2 31–37.
IEEE S. Kıncal, C. Topkaya, R. Güp, and T. Hökelek, “ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID”, MJST, vol. 8, no. 2, pp. 31–37, 2022, doi: 10.22531/muglajsci.1099935.
ISNAD Kıncal, Sultan et al. “ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID”. Mugla Journal of Science and Technology 8/2 (December 2022), 31-37. https://doi.org/10.22531/muglajsci.1099935.
JAMA Kıncal S, Topkaya C, Güp R, Hökelek T. ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID. MJST. 2022;8:31–37.
MLA Kıncal, Sultan et al. “ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID”. Mugla Journal of Science and Technology, vol. 8, no. 2, 2022, pp. 31-37, doi:10.22531/muglajsci.1099935.
Vancouver Kıncal S, Topkaya C, Güp R, Hökelek T. ANALYSIS OF THE CRYSTAL STRUCTURE AND ENERGY FRAMEWORKS OF 5-ACETIL-1,3-DIMETHYL BARBITURIC ACID. MJST. 2022;8(2):31-7.
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