Quadricyclane is a strained, multi-cyclic hydrocarbon with the formula CH2(CH)6. A white volatile colorless liquid, it is highly strained molecule (78.7 kcal/mol). Isomerization of quadricyclane proceeds slowly at low temperatures.[1] Because of quadricyclane's strained structure and thermal stability, it has been studied extensively.
Quadricyclane is produced by the irradiation of norbornadiene (bicyclo[2.2.1]hepta-2,5-diene)[2] in the presence of Michler's ketone or ethyl Michler's ketone.[3] Other sensitizers, such as acetone, benzophenone, acetophenone, etc., may be used but with a lesser yield. The yield is higher for freshly distilled norbornadiene, but commercial reagents will suffice.[2]
Proposed applications to solar energyedit
The conversion of norbornadiene into quadricyclane is achieved with ~300 nm UV radiation.[4] When converted back to norbornadiene, ring strain energy is liberated in the form of heat (ΔH = −89 kJ/mol). This reaction has been proposed to store solar energy.[5][6] However, the absorption edge of light does not extend past 300 nm whereas most solar radiation has wavelengths longer than 400 nm. Quadricyclane's relative stability and high energy content have also given rise to its use as a propellant additive or fuel. However, quadricyclane undergoes thermal decomposition at relatively low temperatures (less than 400 °C). This property limits its applications, as propulsion systems may operate at temperatures exceeding 500 °C.[7]
Reactionsedit
Quadricyclane readily reacts with acetic acid to give a mixture of nortricyclyl acetate and exo-norbornyl acetate.[1] Quadricyclane also reacts with many dienophiles to form 1:1 adducts.[2]
Notesedit
Wikimedia Commons has media related to Quadricyclane.
^ abPetrov, V. A; Vasil’ev, N. V. “Synthetic Chemistry of Quadricyclane.” Current Organic Synthesis 3 (2006): 215–259
^ abcSmith, Claiborune D. (1971). "Quadricyclane". Organic Syntheses. doi:10.15227/orgsyn.051.0133.
^Cahill, P; Steppel, R. Process of quadricyclane production. U.S. Patent 10,661,194 filed September 12, 2003, and issued March 18, 2004
^Kalsi, P S (2000). Organic Reactions And Their Mechanisms. New Age International. p. 366. ISBN978-81-224-1268-0.
^Dubonosov, A. D; Bren, V. A; Chernoivanov, V. A. “Norbornadiene – quadricyclane as an abiotic system for the storage of solar energy.” Russian Chemical Reviews 71 (2002): 917–927
^Philippopoulos, Constantine; Economou, Dimitrios; Economou, Constantine; Marangozis, John (1983). "Norbornadiene-quadricyclane system in the photochemical conversion and storage of solar energy". Industrial & Engineering Chemistry Product Research and Development. 22 (4): 627. doi:10.1021/i300012a021.
^Striebich, R; Lawrence, J (2003). "Thermal decomposition of high-energy density materials at high pressure and temperature". Journal of Analytical and Applied Pyrolysis. 70 (2): 339. doi:10.1016/S0165-2370(02)00181-X.
November 16, 2023
quadricyclane, strained, multi, cyclic, hydrocarbon, with, formula, white, volatile, colorless, liquid, highly, strained, molecule, kcal, isomerization, quadricyclane, proceeds, slowly, temperatures, because, quadricyclane, strained, structure, thermal, stabil. Quadricyclane is a strained multi cyclic hydrocarbon with the formula CH2 CH 6 A white volatile colorless liquid it is highly strained molecule 78 7 kcal mol Isomerization of quadricyclane proceeds slowly at low temperatures 1 Because of quadricyclane s strained structure and thermal stability it has been studied extensively Quadricyclane NamesPreferred IUPAC name Tetracyclo 3 2 0 02 7 04 6 heptaneOther names quadricyclo 2 2 1 02 6 03 5 heptane tetracyclo 2 2 1 02 6 03 5 heptaneIdentifiersCAS Number 278 06 8 Y3D model JSmol Interactive imageChemSpider 30796462 NECHA InfoCard 100 005 450EC Number 205 994 1PubChem CID 78961UNII 8E0K9BG24C YCompTox Dashboard EPA DTXSID30182121InChI InChI 1S C7H8 c1 2 4 5 2 7 3 1 6 4 7 h2 7H 1H2 t2 3 4 5 6 7 NKey DGZUEIPKRRSMGK BEOVHNCFSA N NInChI 1 C7H8 c1 2 4 5 2 7 3 1 6 4 7 h2 7H 1H2 t2 3 4 5 6 7 Key DGZUEIPKRRSMGK BEOVHNCFBKSMILES C1C2C3C2C4C1C34PropertiesChemical formula C7H8Molar mass 92 14 g molDensity 0 982 g cm3Melting point 44 C 47 F 229 K Boiling point 108 C 226 F 381 K at 987 hPaSolubility in water InsolubleHazardsGHS labelling PictogramsSignal word DangerHazard statements H226 H330Precautionary statements P210 P260 P284 P310Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Proposed applications to solar energy 3 Reactions 4 NotesPreparation editQuadricyclane is produced by the irradiation of norbornadiene bicyclo 2 2 1 hepta 2 5 diene 2 in the presence of Michler s ketone or ethyl Michler s ketone 3 Other sensitizers such as acetone benzophenone acetophenone etc may be used but with a lesser yield The yield is higher for freshly distilled norbornadiene but commercial reagents will suffice 2 nbsp Proposed applications to solar energy editThe conversion of norbornadiene into quadricyclane is achieved with 300 nm UV radiation 4 When converted back to norbornadiene ring strain energy is liberated in the form of heat DH 89 kJ mol This reaction has been proposed to store solar energy 5 6 However the absorption edge of light does not extend past 300 nm whereas most solar radiation has wavelengths longer than 400 nm Quadricyclane s relative stability and high energy content have also given rise to its use as a propellant additive or fuel However quadricyclane undergoes thermal decomposition at relatively low temperatures less than 400 C This property limits its applications as propulsion systems may operate at temperatures exceeding 500 C 7 Reactions editQuadricyclane readily reacts with acetic acid to give a mixture of nortricyclyl acetate and exo norbornyl acetate 1 Quadricyclane also reacts with many dienophiles to form 1 1 adducts 2 Notes edit nbsp Wikimedia Commons has media related to Quadricyclane a b Petrov V A Vasil ev N V Synthetic Chemistry of Quadricyclane Current Organic Synthesis 3 2006 215 259 a b c Smith Claiborune D 1971 Quadricyclane Organic Syntheses doi 10 15227 orgsyn 051 0133 Cahill P Steppel R Process of quadricyclane production U S Patent 10 661 194 filed September 12 2003 and issued March 18 2004 Kalsi P S 2000 Organic Reactions And Their Mechanisms New Age International p 366 ISBN 978 81 224 1268 0 Dubonosov A D Bren V A Chernoivanov V A Norbornadiene quadricyclane as an abiotic system for the storage of solar energy Russian Chemical Reviews 71 2002 917 927 Philippopoulos Constantine Economou Dimitrios Economou Constantine Marangozis John 1983 Norbornadiene quadricyclane system in the photochemical conversion and storage of solar energy Industrial amp Engineering Chemistry Product Research and Development 22 4 627 doi 10 1021 i300012a021 Striebich R Lawrence J 2003 Thermal decomposition of high energy density materials at high pressure and temperature Journal of Analytical and Applied Pyrolysis 70 2 339 doi 10 1016 S0165 2370 02 00181 X Retrieved from https en wikipedia org w index php title Quadricyclane amp oldid 1155263701, wikipedia, wiki, book, books, library,
