Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone (THBQ, THQ), is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.
The compound gives a light red solution in water,[2] and crystallizes as the glistening bluish-black (but non-conducting) dihydrateC6O2(OH)4·2H2O.[2][3]
Like most phenols, THBQ is acidic and easily loses the four hydrogen ions from the hydroxyl groups, yielding anions such as C6H2O2−6 and C6O4−6. The latter is symmetric and aromatic, as the double bonds and negative charges are evenly distributed over the six CO groups.
The black tetrapotassium salt K4C6O6 was prepared by West and Niu in 1962, by reacting THBQ with potassium methoxide in methanol. The salt is diamagnetic and the infrared spectrum suggests that the C–C and C–O distances are all equal, with the ring slightly distorted in the "chair" conformation.[12] Partial oxidation of K4C6O6 affords a green, strongly paramagnetic solid, conjectured to be 3K+·C6O3−6, and complete oxidation yields potassium rhodizonate2K+·C6O2−6.[12]
The greenish-black sodium salt Na4C6O6 was described by Fatiadi and Sanger in 1962.[4]
The dark-violet lithium salt Li4C6O6 has been proposed as an electrode material for batteries as it can be oxidized to the rhodizonate Li2C6O6 and reduced to the hexahydroxybenzene salt Li6C6O6.[5] In the absence of oxygen, Li4C6O6 is stable to about 450 °C and then decomposes leaving a residue of lithium carbonate.[5] Indeed, the rhodizonate appears to disproportionate at about 400 °C into Li4C6O6 and cyclohexanehexoneC6O6 that promptly decomposes into carbon monoxide, carbon dioxide, and carbon.[5]Li4C6O6 forms a hydrateLi4C6O6·2H2O that loses its water at about 250 °C.[5]
^ abKlug, H. P. (1965). "The crystal structure of tetrahydroxy-p-benzoquinone". Acta Crystallographica. 19 (6): 983. doi:10.1107/S0365110X65004760.
^ abMiller, M. W. (1961). Microbial Metabolites. McGraw-Hill.
^ abFatiadi, A. J.; Sanger, W. F. "Tetrahydroxyquinone". Organic Syntheses. 42: 90.; Collective Volume, vol. 5, p. 1011
^ abcdeChen, H.; Armand, M.; Courty, M.; Jiang, M.; Grey, C. P.; Dolhem, F.; Tarascon, J.-M.; Poizot, P. (2009). "Lithium salt of tetrahydroxybenzoquinone: toward the development of a sustainable Li-ion battery". Journal of the American Chemical Society. 131 (25): 8984–8988. doi:10.1021/ja9024897. PMID 19476355.
^Cowan, J. A.; Howard, J. A. K.; Leech, M. A. (2001). "Interpenetrating supramolecular lattices in 4,4′-bipyridine-2,3,5,6-tetrahydroxy-1,4-benzoquinone (3/2)". Acta Crystallographica Section C. 57 (10): 1196–1198. doi:10.1107/S0108270101011647. PMID 11600783.
^Hof, T. (1935). Recueil des travaux botaniques néerlandais [Collection of Dutch botanical works] (in French). Vol. 32. New Zealand: F.E. Macdonald; Dutch Botanical Society. p. 92. OCLC 312975183.{{cite book}}: CS1 maint: date and year (link)
^Kluyver, A. J.; Hof, T.; Boezaardt, A. G. J. (1939). "On the pigment of Pseudomonas beijerinckii Hof (Chromohalobacter beijerinckii)". Enzymologia. 7 (257).{{cite journal}}: CS1 maint: date and year (link)[full citation needed]
^Elvehjem, C. A. (June 1947). "Vitamins and Hormones—Advances in Research and Applications". American Journal of Public Health and the Nation's Health. 37 (6): 776. doi:10.2105/AJPH.37.6.776. ISSN 0002-9572. PMC1623712.
^Underkofler, L. A.; Hickey, R. J. (1954). Industrial Fermentations.[page needed]
^Preisler, P. W.; Berger, L. (1942). "Preparation of tetrahydroxyquinone and rhodizonic acid salts from the product of the oxidation of inositol with nitric acid". Journal of the American Chemical Society. 64 (1): 67–69. doi:10.1021/ja01253a016.
^ abWest, R.; Niu, H. Y. (1962). "Symmetrical Resonance Stabilized Anions, CnO−m n. II. K4C6O6 and Evidence for C6O−3 6". Journal of the American Chemical Society. 84 (7): 1324–1325. doi:10.1021/ja00866a068.
October 20, 2023
tetrahydroxy, benzoquinone, also, called, tetrahydroxy, benzoquinone, tetrahydroxybenzoquinone, tetrahydroxyquinone, thbq, organic, compound, with, formula, c6o2, molecular, structure, consists, cyclohexadiene, ring, with, four, hydroxyl, groups, ketone, group. Tetrahydroxy 1 4 benzoquinone also called tetrahydroxy p benzoquinone tetrahydroxybenzoquinone or tetrahydroxyquinone THBQ THQ is an organic compound with formula C6O2 OH 4 Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite para positions Tetrahydroxy 1 4 benzoquinone 1 NamesPreferred IUPAC name 2 3 5 6 Tetrahydroxycyclohexa 2 5 diene 1 4 dioneOther names TetroquinoneIdentifiersCAS Number 319 89 1 Y3D model JSmol Interactive imageChEBI CHEBI 137472ChEMBL ChEMBL1329029ChemSpider 5231 YECHA InfoCard 100 005 706EC Number 206 275 5KEGG D06096PubChem CID 5424UNII U7L4P6H0SU YCompTox Dashboard EPA DTXSID9045897InChI InChI 1S C6H4O6 c7 1 2 8 4 10 6 12 5 11 3 1 9 h7 8 11 12HKey DGQOCLATAPFASR UHFFFAOYSA NSMILES O C C O C1O C O C O C1 OPropertiesChemical formula C 6H 4O 6Molar mass 172 092 g mol 1Appearance Blue black crystalsDensity 2 609 g cm3Boiling point 370 6 C 699 1 F 643 8 K at 760 mmHgSolubility in water Slightly soluble in cold waterHazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Flash point 192 1 C 377 8 F 465 2 K Except 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 The compound gives a light red solution in water 2 and crystallizes as the glistening bluish black but non conducting dihydrate C6O2 OH 4 2H2O 2 3 The compound can be synthesized from glyoxal 4 or from myo inositol a natural compound widely present in plants 5 THBQ forms an adduct with 4 4 bipyridine in a 2 3 ratio 6 Salts of THBQ EditLike most phenols THBQ is acidic and easily loses the four hydrogen ions from the hydroxyl groups yielding anions such as C6H2O2 6 and C6O4 6 The latter is symmetric and aromatic as the double bonds and negative charges are evenly distributed over the six CO groups The calcium salt Ca2C6O6 is the dark purple pigment produced from inositol by Chromohalobacter beijerinckii in the fermentation of salt beans already noted by T Hof in 1935 3 7 8 9 10 The dark purple and insoluble dipotassium salt K2C6H2O6 was prepared by Preisler and Berger in 1942 by oxidizing inositol with nitric acid and reacting the result with potassium carbonate in the presence of oxygen Reaction of this salt with hydrochloric acid produces THBQ in good yield 11 The black tetrapotassium salt K4C6O6 was prepared by West and Niu in 1962 by reacting THBQ with potassium methoxide in methanol The salt is diamagnetic and the infrared spectrum suggests that the C C and C O distances are all equal with the ring slightly distorted in the chair conformation 12 Partial oxidation of K4C6O6 affords a green strongly paramagnetic solid conjectured to be 3K C6O3 6 and complete oxidation yields potassium rhodizonate 2K C6O2 6 12 The greenish black sodium salt Na4C6O6 was described by Fatiadi and Sanger in 1962 4 The dark violet lithium salt Li4C6O6 has been proposed as an electrode material for batteries as it can be oxidized to the rhodizonate Li2C6O6 and reduced to the hexahydroxybenzene salt Li6C6O6 5 In the absence of oxygen Li4C6O6 is stable to about 450 C and then decomposes leaving a residue of lithium carbonate 5 Indeed the rhodizonate appears to disproportionate at about 400 C into Li4C6O6 and cyclohexanehexone C6O6 that promptly decomposes into carbon monoxide carbon dioxide and carbon 5 Li4C6O6 forms a hydrate Li4C6O6 2H2O that loses its water at about 250 C 5 References Edit Tetroquinone The Merck Index 11th ed p 9177 a b Klug H P 1965 The crystal structure of tetrahydroxy p benzoquinone Acta Crystallographica 19 6 983 doi 10 1107 S0365110X65004760 a b Miller M W 1961 Microbial Metabolites McGraw Hill a b Fatiadi A J Sanger W F Tetrahydroxyquinone Organic Syntheses 42 90 Collective Volume vol 5 p 1011 a b c d e Chen H Armand M Courty M Jiang M Grey C P Dolhem F Tarascon J M Poizot P 2009 Lithium salt of tetrahydroxybenzoquinone toward the development of a sustainable Li ion battery Journal of the American Chemical Society 131 25 8984 8988 doi 10 1021 ja9024897 PMID 19476355 Cowan J A Howard J A K Leech M A 2001 Interpenetrating supramolecular lattices in 4 4 bipyridine 2 3 5 6 tetrahydroxy 1 4 benzoquinone 3 2 Acta Crystallographica Section C 57 10 1196 1198 doi 10 1107 S0108270101011647 PMID 11600783 Hof T 1935 Recueil des travaux botaniques neerlandais Collection of Dutch botanical works in French Vol 32 New Zealand F E Macdonald Dutch Botanical Society p 92 OCLC 312975183 a href Template Cite book html title Template Cite book cite book a CS1 maint date and year link Kluyver A J Hof T Boezaardt A G J 1939 On the pigment of Pseudomonas beijerinckii Hof Chromohalobacter beijerinckii Enzymologia 7 257 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint date and year link full citation needed Elvehjem C A June 1947 Vitamins and Hormones Advances in Research and Applications American Journal of Public Health and the Nation s Health 37 6 776 doi 10 2105 AJPH 37 6 776 ISSN 0002 9572 PMC 1623712 Underkofler L A Hickey R J 1954 Industrial Fermentations page needed Preisler P W Berger L 1942 Preparation of tetrahydroxyquinone and rhodizonic acid salts from the product of the oxidation of inositol with nitric acid Journal of the American Chemical Society 64 1 67 69 doi 10 1021 ja01253a016 a b West R Niu H Y 1962 Symmetrical Resonance Stabilized Anions CnO mn II K4C6O6 and Evidence for C6O 36 Journal of the American Chemical Society 84 7 1324 1325 doi 10 1021 ja00866a068 Retrieved from https en wikipedia org w index php title Tetrahydroxy 1 4 benzoquinone amp oldid 1173478108, wikipedia, wiki, book, books, library,
