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2,4,6-Trinitrofenol ve Trinitrotoluen ile 1-Bromopiren Arasında Oluşan Yeni Enerjik Ko-kristalin Karakterizasyonu ve Enerjik Performans Özellikleri

Year 2019, Volume: 14 Issue: 1, 136 - 149, 31.05.2019
https://doi.org/10.29233/sdufeffd.537748

Abstract

Ko-kristallendirme, 1:1
molar oranda Pikrik asit ile 1-Bromopiren ve TNT ile 1-Bromopiren arasında
çözücü buharlaştırma yöntemiyle hazırlandı ve ko-kristallerin yapısı tek
kristal ve toz X ışını kırınımı, Kütle spektrometresi, Kızılötesi
spektroskopisi ile karekterize edildi. Kırınım verileri analizi,
ko-kristallerin öncelikle donor-alıcı (elektron verici-elekton alıcı) π…π
istifleme etkileşimlerinden oluştuğunu ortaya koydu. Darbe hassasiyeti testleri
sonucu yapılan ölçümler ile TNT: 1-Bromopiren ve Pikrik Asit: 1-Bromopiren
ko-kristalleri, saf TNT, Picric Acid'e kıyasla önemli ölçüde azaltılmış darbe
duyarlılığını göstermiştir. Elde edilen yeni enerjik ko-kristaller detaylı calışması
ile  yoğunluk, oksijen dengesi, erime
noktası, ayrışma sıcaklığı, patlama performansı (hız, basınç) gibi önemli
fiziksel ve kimyasal özelliklerin değiştiğini ortaya koymaktadır.
Ko-kristalizasyon calişmasi ile  yeni
keşfedilen alternatif enerjik maddelerin iyileştirilmiş özelliğe sahip olduğunu
ve mevcut enerjik materyalin fiziksel ve kimyasal özelliklerini değiştirmenin
etkili bir yöntem olduğunu vurgulamaktadır.

References

  • A. Becuwe, A. Delclos,“Low‐sensitivity explosive compounds for low vulnerability warheads.”, Propell. Explos. Pyrotech., 18(1), 1-10, 1993.
  • A. Zhurova, V. V. Zhurov and A. A. Pinkerton, “ Structure and Bonding in β-HMX-Characterization of a Trans-Annular N...N Interaction.”, JACS, 129(45), 13887-13893, 2007.
  • H. Östmark, S. Wallin, and P. Goede,” High energy density materials (HEDM): overview, theory and synthetic efforts at FOI.”, CEJEM, 4(1-2), 83-108, 2007.
  • T. Klapötke, C. Janiak, and R. Alsfasser, Moderne Anorganische Chemie, Berlin:Walter de Gruyter, 2007.
  • R. P. Singh, R. D. Verma, D. T. Meshri, J. N. M. Shreeve, “Energetic nitrogen-rich salts and ionic liquids.” Angew. Chem., 45(22), 3584-3601, 2006.
  • T. M. Klapötke, “New nitrogen-rich high explosives”, High Energy Density Materials, Springer, Berlin: Heidelberg, 2007, pp. 85-121.
  • K. B. Landenberger, “Cocrystallization of Energetic Materials”, PhD thesis, The Univ. of Michigan, Michigan, USA, 2013.
  • M. Jaidann, S. Roy, H. Abou-Rachid and L. S. Lussier, “A DFT theoretical study of heats of formation and detonation properties of nitrogen-rich explosives”, J. Hazard. Mater., 176(1-3), 165-173, 2010.
  • T. Clark, M. Hennemann, J. S. Murray, P. Politzer, “ Halogen bonding: the σ-hole”, J. Mol. Model, 13, 291-296, 2007.
  • P. Politzer, J. S. Murray, J. M. Seminerio, P. Lane, M. E. Grice, M. C. Concha, “Computational characterization of energetic materials”, J. Mol Struc-Theochem, 573(1-3), 1-10, 2001.
  • L. Türker, T. Atalar, S. Gümüş, Y. Çamur, “A DFT study on nitrotriazines”, J. Hazard. Mater., 167(1-3), 440-448, 2009.
  • M.D. Perera, “Hydrogen and halogen bonding in co-crystallization: from fundamentals to applications”, PhD thesis, Dept. of Chemistry, Kansas State Univ., Kansas, USA, 2017.
  • K. B. Landenberger, O. Bolton, and A.J. Matzger, “Energetic–energetic cocrystals of diacetone diperoxide (DADP): Dramatic and divergent sensitivity modifications via cocrystallization.”, JACS, 137(15), 5074-5079, 2015.
  • E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner, I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg, P. Hobza, H. G. Kjaergaard, A. C. Legon, B. Mennucci and D. J. Nesbitt, “Definition of the hydrogen bond (IUPAC Recommendations 2011)”, Pure Appl. Chem., 83(8), 1637-1641, 2011.
  • R. Berger, G. Resnati, P. Metrangolo, E. Weber and J. Hulliger, “Organic fluorine compounds: a great opportunity for enhanced materials properties.”, Chem. Soc. Rev., 40(7), 3496-3508, 2011.
  • J. P. Lommerse, A. J. Stone, R. Taylor and F. H. Allen, “The nature and geometry of intermolecular interactions between halogens and oxygen or nitrogen.”, JACS, 118(13), 3108-3116, 1996.
  • T. F. Headen, C. A. Howard, N. T. Skipper, M. A. Wilkinson, D. T. Bowron and A. K. Soper, “Structure of π− π Interactions in Aromatic Liquids.”, JACS, 132(16), 5735-5742, 2010.
  • J. C. Barnes and W. Golnazarians, “The 1: 1 complex of pyrene with 2, 4, 6-trinitrotoluene.” Acta Crystallogr C Struct Chem., 43(3), 549-552, 1987.
  • O. Bolton and A. J. Matzger, A. J., “Improved stability and smart‐material functionality realized in an energetic cocrystal.”, Angew. Chem., 50(38), 8960-8963, 2011.
  • N. Şen, “N. Characterization and properties of a new energetic co-crystal composed of trinitrotoluene and 2, 6-diaminotoluene”, J. Mol Struct., 1179, 53-461, 2019.
  • N. Şen, “A new cocrystal explosive trinitrotoluene (TNT): 1-amino-4-bromonaphthalene with reduced sensitivity.” Turk. J. Chem., 42(5), 1321-1333, 2018.
  • N. Şen, “A 1: 1 energetic co-crystal formed between trinitrotoluene and 2, 3-diaminotoluene.”, Maced. J. Chem. Chem. En., 37(1), 61-69, 2018.
  • J. Ledgard, “The Preparatory Manual of Explosives.”, 3rd ed., Seattle, Washington USA, 2007, pp. 180.
  • O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K.Howard, H. Puschmann, “OLEX2: A complete structure solution, refinement and analysis program.”, J. Appl. Crystallogr., 42(2), 339–341, 2009.
  • G. M. Sheldrick, “Crystal structure refinement with SHELXL.”, Acta Crystallogr C Struct Chem, A71(1), 3–8, 2015.
  • G. M. Sheldrick, “Crystal structure refinement with SHELXL.”, Acta Crystallogr C Struct Chem, C71, 3–8, 2015.
  • K. L. Kosanke, B. T. Sturman, R. M. Winokur and B. J. Kosanke, “Encyclopedic Dictionary of Pyrotechnics:(and related subjects).”, Journal of Pyrotechnics, Whitewear, CO, USA, 2012.
  • C. D. Fuh, J. S. Lee and C. M. Liaw, “The design aspect of the bruceton test for pyrotechnics sensitivity analysis.”, JDS, 1(1), 83-101, 2003.
  • Gaussian 09, Revision B.01. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L.Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida,T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E.Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox,., Wallingford, CT: Gaussian Inc., 2009.
  • R. Dennington, T. A. Keith and J. Millam, GaussView, Version 5, Semichem Inc., Wallingford, CT, 2009.
  • L.A. Curtiss, K. Raghavachari, P. C. Redfern and J.A. Pople, “Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation.”, J. Chem. Phys., 106, 1063-1079, 1997.
  • E. F. C. Byrd and B. M. Rice, “Improved prediction of heats of formation of energetic materials using quantum mechanical calculations.”, J. Chem. Phys., A113, 5813-5813, 2009.
  • B. M. Rice, S. V. Pai and J. Hare, “Predicting heats of formation of energetic materials quantum mechanical calculations.”, Combus. Flame, 118, 445-458, 1999.
  • P. J. Linstrom and W. G. Mallard, “NIST Standard Reference Database Number 69.”, National Institute of Standards and Technology, Gaithersburg, MD, USA, 2005.
  • K. Molčanov, I. Sabjić and B. Kojić-Prodić, “Face-to-face π-stacking in the multicomponent crystals of chloranilic acid, alkali hydrogenchloranilates, and water.”, Cryst. Eng. Comm., 13, 4211-4217, 2011.
  • H.H. Freedmann, “Intramolecular H-bonds. I. A spectroscopic study of the hydrogen bond between hydroxyl and nitrogen.”, JACS, 83, 2900-2905, 1961.
  • M. J. Kamlet and S. F. Jacobs, “Chemistry of detonations I. A simple method for calculating detonation properties of C-H-N-O explosives.”, J. Chem. Phys., 48, 23-25, 1968.
  • M. J. Kamlet and J. E. Ablard, “Chemistry of detonations. II. Buffered equilibria.”, J.Chem. Phys., 48(1), 36-42, 1968.
  • M. J. Kamlet and C. J. Dickenson, “Chemistry of detonations. III. Evaluation of the simplified calculation method for Chapman-Jouguet detonation pressures on the basis of available experimental information.”, J.Chem. Phys., 48(1), 43-51, 1968.
  • L. Qiu, H. Xiao, X. Gong, X. Ju and W. Zhu, “Theoretical studies on the structures, thermodynamic properties, detonation properties, and pyrolysis mechanisms of spiro nitramines.”, J Phys Chem Biophys., 110(10),3797-3807, 2006.
  • M. J. Kamlet, H. G. Adolph, “The relationship of Impact Sensitivity with Structure of Organic High Explosives. II. Polynitroaromatic explosives”, Propell. Explos. Pyrotech, 4, 30-34, 1979
  • T.M. Klapötke, Chemistry of High-Energy Materials, Walter de Gruyter, 2011, p:75-76.

Characterization and Energetic Performance Properties of New Energetic Co-crystals formed between 2, 4, 6-Trinitrophenol, Trinitrotoluene and 1-Bromopyrene

Year 2019, Volume: 14 Issue: 1, 136 - 149, 31.05.2019
https://doi.org/10.29233/sdufeffd.537748

Abstract

A 1:1 co-crystals of Picric
Acid with 1-Bromopyrene and TNT with 1-Bromopyrene were prepared by a solvent
evaporation method, and the structure of the co-crystals were determined by
single-crystal and powder X-ray diffraction, Mass spectrometry, Infrared
spectroscopy techniques. The diffraction data analysis revealed that the
co-crystals are primarily formed through donor-acceptor π…π stacking
interactions. The TNT:1-Bromopyrene and Picric Acid:1-Bromopyrene co-crystals
indicates significantly reduced impact sensitivity relative to pure TNT, Picric
Acid. A detailed study of the cocrystals formed reveals a modification of
crucial properties including density, oxygen balance, melting point,
decomposition temperature detonation performance (velocity, pressure). The
acquired
results highlight that co-crystallization provides the newly discovered
energetic material with attractive properties, and is an effective way to alter
existing energetic material. 

References

  • A. Becuwe, A. Delclos,“Low‐sensitivity explosive compounds for low vulnerability warheads.”, Propell. Explos. Pyrotech., 18(1), 1-10, 1993.
  • A. Zhurova, V. V. Zhurov and A. A. Pinkerton, “ Structure and Bonding in β-HMX-Characterization of a Trans-Annular N...N Interaction.”, JACS, 129(45), 13887-13893, 2007.
  • H. Östmark, S. Wallin, and P. Goede,” High energy density materials (HEDM): overview, theory and synthetic efforts at FOI.”, CEJEM, 4(1-2), 83-108, 2007.
  • T. Klapötke, C. Janiak, and R. Alsfasser, Moderne Anorganische Chemie, Berlin:Walter de Gruyter, 2007.
  • R. P. Singh, R. D. Verma, D. T. Meshri, J. N. M. Shreeve, “Energetic nitrogen-rich salts and ionic liquids.” Angew. Chem., 45(22), 3584-3601, 2006.
  • T. M. Klapötke, “New nitrogen-rich high explosives”, High Energy Density Materials, Springer, Berlin: Heidelberg, 2007, pp. 85-121.
  • K. B. Landenberger, “Cocrystallization of Energetic Materials”, PhD thesis, The Univ. of Michigan, Michigan, USA, 2013.
  • M. Jaidann, S. Roy, H. Abou-Rachid and L. S. Lussier, “A DFT theoretical study of heats of formation and detonation properties of nitrogen-rich explosives”, J. Hazard. Mater., 176(1-3), 165-173, 2010.
  • T. Clark, M. Hennemann, J. S. Murray, P. Politzer, “ Halogen bonding: the σ-hole”, J. Mol. Model, 13, 291-296, 2007.
  • P. Politzer, J. S. Murray, J. M. Seminerio, P. Lane, M. E. Grice, M. C. Concha, “Computational characterization of energetic materials”, J. Mol Struc-Theochem, 573(1-3), 1-10, 2001.
  • L. Türker, T. Atalar, S. Gümüş, Y. Çamur, “A DFT study on nitrotriazines”, J. Hazard. Mater., 167(1-3), 440-448, 2009.
  • M.D. Perera, “Hydrogen and halogen bonding in co-crystallization: from fundamentals to applications”, PhD thesis, Dept. of Chemistry, Kansas State Univ., Kansas, USA, 2017.
  • K. B. Landenberger, O. Bolton, and A.J. Matzger, “Energetic–energetic cocrystals of diacetone diperoxide (DADP): Dramatic and divergent sensitivity modifications via cocrystallization.”, JACS, 137(15), 5074-5079, 2015.
  • E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner, I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg, P. Hobza, H. G. Kjaergaard, A. C. Legon, B. Mennucci and D. J. Nesbitt, “Definition of the hydrogen bond (IUPAC Recommendations 2011)”, Pure Appl. Chem., 83(8), 1637-1641, 2011.
  • R. Berger, G. Resnati, P. Metrangolo, E. Weber and J. Hulliger, “Organic fluorine compounds: a great opportunity for enhanced materials properties.”, Chem. Soc. Rev., 40(7), 3496-3508, 2011.
  • J. P. Lommerse, A. J. Stone, R. Taylor and F. H. Allen, “The nature and geometry of intermolecular interactions between halogens and oxygen or nitrogen.”, JACS, 118(13), 3108-3116, 1996.
  • T. F. Headen, C. A. Howard, N. T. Skipper, M. A. Wilkinson, D. T. Bowron and A. K. Soper, “Structure of π− π Interactions in Aromatic Liquids.”, JACS, 132(16), 5735-5742, 2010.
  • J. C. Barnes and W. Golnazarians, “The 1: 1 complex of pyrene with 2, 4, 6-trinitrotoluene.” Acta Crystallogr C Struct Chem., 43(3), 549-552, 1987.
  • O. Bolton and A. J. Matzger, A. J., “Improved stability and smart‐material functionality realized in an energetic cocrystal.”, Angew. Chem., 50(38), 8960-8963, 2011.
  • N. Şen, “N. Characterization and properties of a new energetic co-crystal composed of trinitrotoluene and 2, 6-diaminotoluene”, J. Mol Struct., 1179, 53-461, 2019.
  • N. Şen, “A new cocrystal explosive trinitrotoluene (TNT): 1-amino-4-bromonaphthalene with reduced sensitivity.” Turk. J. Chem., 42(5), 1321-1333, 2018.
  • N. Şen, “A 1: 1 energetic co-crystal formed between trinitrotoluene and 2, 3-diaminotoluene.”, Maced. J. Chem. Chem. En., 37(1), 61-69, 2018.
  • J. Ledgard, “The Preparatory Manual of Explosives.”, 3rd ed., Seattle, Washington USA, 2007, pp. 180.
  • O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K.Howard, H. Puschmann, “OLEX2: A complete structure solution, refinement and analysis program.”, J. Appl. Crystallogr., 42(2), 339–341, 2009.
  • G. M. Sheldrick, “Crystal structure refinement with SHELXL.”, Acta Crystallogr C Struct Chem, A71(1), 3–8, 2015.
  • G. M. Sheldrick, “Crystal structure refinement with SHELXL.”, Acta Crystallogr C Struct Chem, C71, 3–8, 2015.
  • K. L. Kosanke, B. T. Sturman, R. M. Winokur and B. J. Kosanke, “Encyclopedic Dictionary of Pyrotechnics:(and related subjects).”, Journal of Pyrotechnics, Whitewear, CO, USA, 2012.
  • C. D. Fuh, J. S. Lee and C. M. Liaw, “The design aspect of the bruceton test for pyrotechnics sensitivity analysis.”, JDS, 1(1), 83-101, 2003.
  • Gaussian 09, Revision B.01. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L.Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida,T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E.Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox,., Wallingford, CT: Gaussian Inc., 2009.
  • R. Dennington, T. A. Keith and J. Millam, GaussView, Version 5, Semichem Inc., Wallingford, CT, 2009.
  • L.A. Curtiss, K. Raghavachari, P. C. Redfern and J.A. Pople, “Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation.”, J. Chem. Phys., 106, 1063-1079, 1997.
  • E. F. C. Byrd and B. M. Rice, “Improved prediction of heats of formation of energetic materials using quantum mechanical calculations.”, J. Chem. Phys., A113, 5813-5813, 2009.
  • B. M. Rice, S. V. Pai and J. Hare, “Predicting heats of formation of energetic materials quantum mechanical calculations.”, Combus. Flame, 118, 445-458, 1999.
  • P. J. Linstrom and W. G. Mallard, “NIST Standard Reference Database Number 69.”, National Institute of Standards and Technology, Gaithersburg, MD, USA, 2005.
  • K. Molčanov, I. Sabjić and B. Kojić-Prodić, “Face-to-face π-stacking in the multicomponent crystals of chloranilic acid, alkali hydrogenchloranilates, and water.”, Cryst. Eng. Comm., 13, 4211-4217, 2011.
  • H.H. Freedmann, “Intramolecular H-bonds. I. A spectroscopic study of the hydrogen bond between hydroxyl and nitrogen.”, JACS, 83, 2900-2905, 1961.
  • M. J. Kamlet and S. F. Jacobs, “Chemistry of detonations I. A simple method for calculating detonation properties of C-H-N-O explosives.”, J. Chem. Phys., 48, 23-25, 1968.
  • M. J. Kamlet and J. E. Ablard, “Chemistry of detonations. II. Buffered equilibria.”, J.Chem. Phys., 48(1), 36-42, 1968.
  • M. J. Kamlet and C. J. Dickenson, “Chemistry of detonations. III. Evaluation of the simplified calculation method for Chapman-Jouguet detonation pressures on the basis of available experimental information.”, J.Chem. Phys., 48(1), 43-51, 1968.
  • L. Qiu, H. Xiao, X. Gong, X. Ju and W. Zhu, “Theoretical studies on the structures, thermodynamic properties, detonation properties, and pyrolysis mechanisms of spiro nitramines.”, J Phys Chem Biophys., 110(10),3797-3807, 2006.
  • M. J. Kamlet, H. G. Adolph, “The relationship of Impact Sensitivity with Structure of Organic High Explosives. II. Polynitroaromatic explosives”, Propell. Explos. Pyrotech, 4, 30-34, 1979
  • T.M. Klapötke, Chemistry of High-Energy Materials, Walter de Gruyter, 2011, p:75-76.
There are 42 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Makaleler
Authors

Nilgün Şen 0000-0002-1997-1312

Sinecan İrem Bozkuş This is me 0000-0002-1106-3424

Publication Date May 31, 2019
Published in Issue Year 2019 Volume: 14 Issue: 1

Cite

IEEE N. Şen and S. İ. Bozkuş, “2,4,6-Trinitrofenol ve Trinitrotoluen ile 1-Bromopiren Arasında Oluşan Yeni Enerjik Ko-kristalin Karakterizasyonu ve Enerjik Performans Özellikleri”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 14, no. 1, pp. 136–149, 2019, doi: 10.29233/sdufeffd.537748.