---------------------------------------------------------------------- David T. Vodak, Matthew Braun, Lykourgos Iordanidis, Jacques Plévert, Michael Stevens, Larry Beck, John C. H. Spence, Michael O'Keeffe, Omar M. Yaghi (2002): "One-Step Synthesis and Structure of an Oligo(spiro-orthocarbonate)". ''Journal of the American Chemical Society'', volume 124, issue 18, pages 4942–4943. {{doi|10.1021/ja017683i}} Linear polymer with alternating tetramethylmethane (neopentane, pentaerythritol) and orthocarbonate groups! ---------------------------------------------------------------------- N. Narasimhamurthy, H. Manohar, Ashoka G. Samuelson, Jayaraman Chandrasekhar (1990): "Cumulative anomeric effect: A theoretical and x-ray diffraction study of orthocarbonates". ''Journal of the American Chemical Society'', volume 112, issue 8, pages 2937–2941. {{doi|10.1021/ja00164a015}} orthocarbonate/ narasimhamurthy-et-al-2002-cumulative-anomeric-effect-a-theoretical-and-x-ray-diffraction-study-of-orthocarbonates.pdf ---------------------------------------------------------------------- H. Meyer, G. Nagorsen (1979): "Structure and reactivity of the orthocarbonic and orthosilicic acid esters of pyrocatechol". ''Angewandte Chemie'' International Edition in English, volume 18, issue 7, pages 551-553. {{doi|10.1002/anie.197905511}} "The first compound found to contain planar tetracoordinated silicon is the orthosilicic ester (2). In contrast, the bonding geometry of the central atom of the analogous orthocarbonic ester deviates only slightly from a tetrahedron. Quantum mechanical studies [e.g. on the model compound (3)] showed that planar tetracoordination is easier for silicon than for carbon. The ability of silicon to engage in sixfold coordination [type(4)] even makes such planar structures easier to achieve than the tetrahedral structure." ---------------------------------------------------------------------- James N. Butler(1967): Review: "Electrochemistry in dimethyl sulfoxide". ''Journal of Electroanalytical Chemistry and Interfacial Electrochemistry'', volume 14, issue 1, pages 89-116. {{doi|10.1016/0022-0728(67)80136-0}} ---------------------------------------------------------------------- M. Giordano, J. Bazán, A. Arvia (1966): "The electrolysis of dimethylsulphoxide solutions of sodium chloride and sodium iodide". ''Electrochimica Acta'', volume 11, issue 7, pages 741-747. {{doi|10.1016/0013-4686(66)87051-2}} "The cathodic reaction involves the initial discharge of sodium ion and subsequent chemical reactions between metallic sodium and the solvent." ---------------------------------------------------------------------- Pietro Tundo, Maurizio Selva (2002): "The Chemistry of Dimethyl Carbonate". ''Accounts of Chemical Research'', volume 35, issue 9, pages 706–716. {{doi|10.1021/ar010076f}} {{pmid|12234200}} dimethylcarbonate/ tundo-selva-2002-the-chemistry-of-dimethyl-carbonate.pdf ---------------------------------------------------------------------- Shizuyoshi Sakai, Yoshitaka Kuroda, Yoshio Ishii (1972): "Preparation of orthocarbonates from thallous alkoxides and carbon disulfide". ''Journal of Organic Chemistry'', volume 37, issue 25, pages 4198–4200. {{doi|10.1021/jo00798a056}} "Thallous ethoxide reacted with equimolar amount of carbon disulfide in dry methylene dichloride to afford tetraethyl orthocarbonate in 97% yield. ... Tetramethyl orthocarbonate was also obtained in good yield by the reaction of Thallous methoxide with carbon disulfide. ... Thallous isopropoxide was prepared by the alcoholysis reaction of thallous methoxide with isopropyl alcohol, and reacted with carbon disulfide in benzene at room temperature to afford tetraisopropyl orthocarbonate in a moderate yield." orthocarbonate/ sakai-et-al-2002-preparation-of-orthocarbonates-from-thallous-alkoxides-and-carbon-disulfide.pdf ---------------------------------------------------------------------- Stanley R. Sandler, Wolf Karo (1986): "Ortho Esters". Chapter 2 in ''Organic Functional Group Preparations'' (Second Edition), pages 48-77. {{doi|10.1016/B978-0-08-092557-8.50006-9}} ---------------------------------------------------------------------- N. Narasimhamurthy, A.G. Samuelson (1986): "Synthesis of aryl orthocarbonates". ''Tetrahedron Letters'', volume 27, issue 8, pages 991-992. {{doi|10.1016/S0040-4039(00)84157-X}} "A simple and efficient method of preparing tetraaryl orthocarbonates from copper phenoxide and carbon disulfide is described." ---------------------------------------------------------------------- G. G. Birch, M. G. Lindley (1973): "Structural functions of taste in the sugar series: Cyclohexane polyols as sweet analogues of the sugars". ''Journal of Food Science'', volume 38, issue 7, pages 1179-1181. {{doi|10.1111/j.1365-2621.1973.tb07232.x}} Analyzes the swetness of several cyclohexane alcohols with 1 to 6 hydroxyls. Including epi, allo, neo, myo, muco, D-chyro and L=chiro inositol (no scyllo, or cis). Only allo and the two chiro are sweet; the others (including myo) are only "trace sweet". inositol/ birch_structural_taste.pdf ---------------------------------------------------------------------- Yunjie Li, Pingping Han, Juan Wang, Ting Shi, Chun You (2021): "Production of myo-inositol: Recent advance and prospective". ''Biotechnology and Applied Biochemistry'', volume 69, issue 3, pages 1101-1111. {{doi|10.1002/bab.2181}} g inositol/ li_production_of_myo_inositol.pdf ---------------------------------------------------------------------- Keran Ma, Lynsie A.M. Thomason, JoAnne McLaurin (2012): "''scyllo''-Inositol, preclinical, and clinical data for Alzheimer's disease". Chapter of ''Advances in Pharmacology'', volume 64, pages 177–212. {{doi|10.1016/B978-0-12-394816-8.00006-4}} {{PMID|22840748}} {{isbn|9780123948168}} inositol/ 1-s2.0-B9780123948168000064-main.pdf ---------------------------------------------------------------------- G. W. Beadle and E. L. Tatum (1945): "Neurospora: II. Methods of Producing and Detecting Mutations Concerned with Nutritional Requirements". ''American Journal of Botany'', volume 32, issue 10, pages 678-686. {{doi|10.2307/2437625}} Uses the fungi ''[[Neurospora crassa]]' and ''[[Neurospora sitophyla]]'' to produce ''myo''-inositol; ---------------------------------------------------------------------- Dilay Kepil (2020): ''Synthesis, structural characterization and chemistry of tribenzoheterotriquinane based molecular structures'', Masters Thesis, Middle East Technical University. {{doi|}} oxonium/ dilay-kepil-thesis-tribenzoheterotriquinane.pdf ---------------------------------------------------------------------- Hong-Kun Zhao, Dao-Sen Zhang, Cao Tang, Rong-Rong Li, Ming-Li Su, Wen-Lin Xu, Ya-Qiong Wang (2007): "Solubility and phase diagram for the ternary sodium oxalate + hydrogen peroxide + water system at (283.15 and 293.15) K". ''Journal of Chemical Engineering Data'', volume 52, issue 3, pages 863-865. {{doi|10.1021/je060461l}} "Several perhydrates such as Na2CO3‚1.5H2O2, CO(NH2)2‚H2O2, 4Na2SO4‚2H2O2‚NaCl, etc. have been produced and used in industry. Pederson1 synthesized a new hydrogen peroxide adduct with sodium oxalate, with the formula Na2C2O4‚H2O2 by the following approach: sodium oxalate was dissolved in perhydrol (30 % H2O2). By slow evaporation, the crystals of Na2C2O4‚H2O2 were formed as needles along the R axis. ... The oxalate ion and the hydrogen peroxide molecule are centrosymmetric. The structure is built up of endless chains of alternating hydrogen peroxide molecules and oxalates ions linked together by hydrogen bonds. Na2C2O4 crystallizes anhydrous from H2O, solubility 2.95% (mass) at 10 C, 3.40% at 20 C. No hydrates at 10 C or 20 C. Na2C2O4.H2O2 only perhydrate seen in region investigated (up to 60% mass of H2O2). ---------------------------------------------------------------------- A. J. Henry (1948): "The toxic principle of ''Courbonia virgata'': Its isolation and identification as a tetramethylammonium salt". ''British Journal of Pharmacology and Chemotherapy'', volume 3, issue 3, pages 187-188. {{doi|10.1111/j.1476-5381.1948.tb00373.x}} "A tuberous root submitted for examination from the Southern Sudan as having been concerned in the death of two women and since identified at Kew as ''Courbonia virgata'' A. Brongn., a member of the Capparidaceae..." Toxin was a base that was isolatd as the iodide of tetramethylammonium (tetramine), colourless, stable up to 400 C. Picrate melts at 315 C. Previously found only in a sea anemone ''Actinia equina'' Fresh root contains ~0.2% of the base, and ~0.25 g of the base, orally, is lethal withing one hour. LD mouse 0.5-1.0 mg per 25 g of body weight. Daily sub-lethal doses did not create immunity. tetramethylammonium/ Courbonia_virgata_toxin.pdf ---------------------------------------------------------------------- A. J. Henry, D. N. Grindley (1949): "Courbonia Virgata: Its chemical composition and basic constituents". ''Journal of Chemical Technology and Biotechnology'', volume 68, issue 1, pages 9-12. {{doi|10.1002/jctb.5000680103}} "The isolation of tetramine (tetramethylammonium hydroxide) as the iodide from the root of Courbonia virgara is described, and its distribution in various pans of the plant is recorded. The presence also of di- and trimethylmine has been proved, and of quaternary bases other than tetramine induced. The carbohydrate material of the root is partly sucrose and partly araban, reducing sugars and starch being absent; while that of the seeds is mainly starch together with a little pentosan, sucrose and reducing sugars being absent. The constants and fatty acid composition of the root fat have been determined and the composition of the ash of the root is also given." ---------------------------------------------------------------------- J. W. Cornforth and Alan J. Henry (1952): "The presence of cis- and trans-3-hydroxystachydrine in the fruit of ''Courbonia virgata''". ''Journal of the Chemical Society (Resumed)'', volume 1952, article 107, pages 597-601. {{doi|10.1039/JR9520000597}} Kernel of ''Courbonia virgata'' contains some tetramethylammonium, not as much as the root (that contains the nitrate, extrated with ethanol). Husk contains cis and trans stachydrine hydroxide, which has a quaternary ammonium core. ---------------------------------------------------------------------- Alan J. Henry and Harold King (1950): "The isolation and identification of (–)-stachydrine ethyl ester periodide from the root of ''Courbonia virgata''". ''Journal of the Chemical Society (Resumed)'', volume 1950, article 556, pages 2866-2868. {{doi|10.1039/JR9500002866}} ---------------------------------------------------------------------- William F.H. McLean, Gerald Blunden, Kenneth Jewers (1996): "Quaternary ammonium compounds in the Capparaceae". ''Biochemical Systematics and Ecology'', volume 24, issue 5, pages 427-434. {{doi|10.1016/0305-1978(96)00044-0}} Other species in the family have betaines and other quaternary ammonium compounds. ---------------------------------------------------------------------- A. E. Lapshin, E. F. Medvedev, I. G. Polyakova, and Yu. F. Shepelev (2009): "Synthesis and crystal structure of a new modification of sodium tetrahydroxyborate NaB(OH)4". ''Glass Physics and Chemistry'', volume 35, issue 3, pages 308–312. First published in ''Fizika i Khimiya Stekla''. {{doi|10.1134/S1087659609030110}} "It was shown using IR spectroscopy that the boric acid used (special-purity grade) was actually a mixture of metaboric and orthoboric acids and amorphous boron oxide" "aqueous solutions of 'boric acid' and sodium hydroxide were mixed by adding an alkaline solution with a dosing device to the boric acid solution (pH 5) until pH 12 was attained. The calculated borate ratio NB of the prepared solution was, on average (for solutions with different initial concentrations of reagents) [B2O3]/[Na2O] = 1.5." Evaporation in air at room temperature yielded needle crystals with formula H4NaBO4 or [Na+][B(OH)4]-, apparently less dense than the solution. In crystallization of borate from aqueous solutions, the borate ratio in the crystal depends on the pH of the solution rather than the concentration of B2O3 or nature of cation. At pH 12 the ratio is 1:1 Na:B. Crystals become dull on exposure to air, perhaps by reaction with CO2, but the product is not detectable. Crystals are comprised of Na+ ions and [B(OH)4]- ions. Orthorhombic crystal system, cell parameteres at ~20 C: ''a'' = 532.3 ''b'' = 949.6, ''c'' = 659.6 pm, ''Z'' = 4, space group P2_1 2_1 2_1, cell volume 0.3334 nm^3, density (calc.) 2.029 g/cm^3. Atom coordinates (nm?): Na +0.7140 | –0.0199 | +0.9668 O1 +0.8622 | +0.3791 | +0.9407 O2 +0.8749 | +0.3819 | +0.5745 O3 +0.4950 | +0.3121 | +0.7439 O4 +0.8556 | +0.1613 | +0.7583 B +0.7724 | +0.3106 | +0.7556 H1 +0.778 | +0.448 | +0.966 H2 +0.893 | +0.330 | +0.492 H3 +0.442 | +0.268 | +0.841 H4 +1.002 | +0.158 | +0.786 Selected atom distances (pm): Na–O4 232.80 Na–O4i 234.4 Na–O1ii 238.00 Na–O3iii 239.09 Na–O2iv 239.42 O1–B 146.44 O2–B 147.75 O3–B 147.84 O4–B 148.47 Hydrogen bond lengths (pm) and angles (degrees): O–H...O O–H H...O O...O O–H–O O1–H1...O2 081 195 274.2 167 O2–H2...O3 074 213 286.5 173 O3–H3...O1 081 205 285.0 167 O4–H4...O1 080 266 337 150 Symmetry codes: (i) –x + 3/2, –y, z + 1/2; (ii) x – 1/2, –y + 1/2, –z + 2; (iii) –x + 1, y – 1/2, –z + 3/2; (iv) –x + 2, y – 1/2, –z + 3/2. The B(OH)4 tetrahedra are linked together only by hydrogen bonds. The B(OH)4 tetrahedra are in layers parallel to the (010) plane, 224 pm apart. All tetrahedra in each layer are oriented in the same direction and thos in adjacent layers are oriented in opposite directions. The boron tetrahedra are hydrogen-bonded within and across layers. Sodium atoms lie between the layers. Another form was described by Csetenyi et al (1993): borate/ lapshin-et-al-2009-another-NaBO4H4.pdf ---------------------------------------------------------------------- L. J. Csetenyi, F. P. Glasser, R. A. Howie (1993): "Structure of Sodium Tetrahydroxyborate". ''Acta Crystallographica, Section C: Crystal Structure Communications'', volume 49, issue , pages 1039–1041. {{doi|10.1107/S0108270193000058}} Cited by Lapshin et al (2009): Monoclinic system, ''a'' = 588.6, ''b'' = 1056.6, ''c'' = 614.3, ''β'' = 111.6°, group P2_1/a. Same ions but the B(OH)4 tetrahedra are alternately central-flipped. The sodium ions are inside the layers not between them. ---------------------------------------------------------------------- Esam A. Gomaa (2013): [http://epa.niif.hu/02200/02286/00015/pdf/EPA02286_European_Chemical_Bulletin_2013_05_259-261.pdf "Solvation parameters for sodium oxalate in mixed ethanol-water solvents at 301.15 K"]. ''European Chemical Bulletin'', volume 2, issue 5, pages 259-261. No DOI? Graph of solubility with varying ethanol concentration has two unexplained kinks. Should have made more measurements around those points. What the heck is solubility S in g/mol? Table 1. Molar solubilities (S), log activity coefficients (γ±), solubility products (pKsp) and free energies of solvation (∆G and ∆Gt) for (Na2Ox) in different ethanol-water solvents at 301.15 K. Xs, mole fraction of ethanol molar solubility S, g.mol-1 log activity coefficient log γ± solubility product pKsp free energy of solvation ∆G, kJ mol-1 Gibbs free energy of transfer ∆Gt, kJ mol-1 0.0000 7.91 -1.4236 -8.9909 -51.8433 0 0.0330 7.65 -1.4001 -8.8530 -51.0484 0.7949 0.0715 7.16 -1.3535 -8.5780 -49.4624 2.3809 0.1166 6.45 -1.3344 -8.4656 -48.814 3.0297 0.1703 6.750 -1.3151 -8.3503 -48.1495 3.6938 0.2355 6.61 -1.3014 -8.1764 -47.1467 4.6966 0.3159 6.493 -1.2898 -8.1985 -47.274 4.5693 0.4181 6.250 -1.2655 -8.0517 -46.428 5.4153 0.5591 6.150 -1.2553 -7.9898 -46.0707 5.7726 0.7349 6.051 -1.2451 -7.9279 -45.7138 6.1295 1.0000 5.97 -1.2368 -7.8771 -44.600 7.243 log γ± = -0.5062 S^{0.5} pKsp = -lg4S^3 + 4(log γ±)^3 ∆G = 2.303 RT pKsp ∆Gt = ∆Gs - ∆Gw dicarboxylic_acids_salts/ EPA02286_European_Chemical_Bulletin_2013_05_259-261.pdf ---------------------------------------------------------------------- Qiusheng Yang, Haiou Wang, Xiaoshu Ding, Xue Yang & Yanji Wang (2015): "One-pot synthesis of dimethyl carbonate from carbon dioxide, cyclohexene oxide, and methanol". ''Research on Chemical Intermediates'', volume 41, issue , pages 4101–4111. {{doi|10.1007/s11164-013-1514-4}} Reaction mixes cyclohexene oxide (5 g), CO2, methanol (10 ml) and K2CO3 (0.28g), that acts as catalyst. Other possible catalysts are KI and KBr. Pressure 2.6 MPa 150 C for 6 h. Other byproducts are 1,2-cyclohexanediol and 2-methoxycyclohexanol K2CO3 and KI are soluble in DMC. K2CO3 gets transformed into the actual catalyst and disappears. Conjectures that K2CO3 reacts with CH3OH to form a dissolved CH3OK and then it inserts CO2 to obtain a stable CH3OCO2K. dimethylcarbonate/ s11164-013-1514-4.pdf ---------------------------------------------------------------------- Yanhong Chang, Tao Jiang, Buxing Han, Zhimin Liu, Weize Wu, Liang Gao, Junchun Li, Haixiang Gao, Guoying Zhao, Jun Huang (2004): "One-pot synthesis of dimethyl carbonate and glycols from supercritical CO2, ethylene oxide or propylene oxide, and methanol". ''Applied Catalysis A: General'', volume 263, issue 2, pages 179-186. {{doi|10.1016/j.apcata.2003.12.012}} Cited by about solubilities of KI, KBr, K2CO3. ---------------------------------------------------------------------- T. L. Khotsyanova, R. L. Avoyan (1963): "A preliminary x-ray study of some triphenyloxonium salts". ''Journal of Structural Chemistry'', volume 4, issue , pages 99–100. {{doi|10.1007/BF02237534}} Tested several salts of triphenyloxonium [(C6H5)3O]+ looking for the best one for X-ray study. Concluded that the iodide (anhydrous) was the best among bromide (dihydrate), chloride (dihydrate), tetrafluoroborate (anhydrous) and tetraphenylborate (anhydrous). (Scan is bad so the subscripts are uncertain, and there may be an error with "(C6N5)3O" instead of "(C6H5)3O" in the first entry. Salt | a | b | c | \beta| Z | Group | Z* ---------------------+------+------+------+------+----+------------+--- [(C6H5)3O]I | 933 | 1867 | 956 | ~90 | 4 | P2_1 | 2 [(C6H5)3O]Br.2H2O | 1691 | 2370 | 1678 | ~90 | 16 | I2/c | 2 [(C6H5)3O]Cl.2H2O | 1684 | 2384 | 1666 | ~90 | 16 | I2/c | 2 [(C6H5)3O][BF4] | 949 | 1838 | 952 | ~90 | 4 | P2_1/m | 1 [(C6H5)3O][BF4] | 949 | 1838 | 952 | | 4 | P2_1 | 2 [(C6H5)3O][B(C6H5)4] | 1250 | 1808 | 1386 | | 4 | P2_12_12_1 | 1 Z* = number of crystallographically independent modelcules ---------------------------------------------------------------------- A. N. Nesmeyanov,T. P. Tolstaya (1957): [https://www.mathnet.ru/php/archive.phtml?wshow=paper&jrnid=dan&paperid=22559&option_lang=eng "Triphenyloxonium salts"]. ''Doklady Akademii Nauk SSSR'', Division of Chemical Science, volume 117, issue 4, pages 626–628. {{mathnet|dan22559}} Several salts of [(C6H5)3O]+: Cl-, Br- (with 1.5 H2O), I-, HgI3-, (C6H5)4B-, PtCl6--, Cr2O--, C6H2(No2)3O-, ICl4- oxonium/ nemesyanov-tolstaya-salts-dan22559.pdf ---------------------------------------------------------------------- Robert Taft and Frank H. Welch (1951): "Physical Properties of Aqueous Solutions of Sodium Oxalate, Sodium Malonate, and Sodium Succinate, I". ''Transactions of the Kansas Academy of Science'', volume 54, issue 2, pages 233-246. {{doi|10.2307/3625790}} "White crystalline solids. C2O4 anhydrous, malonate 1H20, succinate 6H2O. Melting points (C) and solubilities (g/dL) of the acids: Oxalic H2C2O4 187.0 10.20 @ 20 C Malonic H4C3O4 135.0 138.00 @ 16 C Succinic H6C4O4 185.0 6.80 @ 20 C Glutaric H8C5O4 97.5 63.90 @ 20 C Adipic H10C6O4 151.0 1.40 @ 15 C Pimelic H12C7O4 105.0 2.50 @ 14 C Suberic H14C8O4 142.0 0.14 @ 16 C Azelaic H16C9O4 106.0 0.20 @ 15 C Sebacic H18C10O4 134.0 0.10 @ 17 C Sodium oxalate and succinate can be procipitated from water solution by addiing ethanol. Sodium malonate can't because of its high solubility in water. Determined properties of solutions as function of concentration: densities, viscosities, surface tensions, refractive indices at 0 C, 25C, and 50C, and freezing point depression. Max depression 0.9 C for oxalate, 4.4 C for malonate, 4.6 C for succinate. ---------------------------------------------------------------------- Jacob G. Reynolds, Michael D. Britton, Robert Carter (2023): "A review of sodium oxalate solubility in water". ''Industrial & Engineering Cehmical Research'', volume 62, pages 19394−19401. {{doi|10.1021/acs.iecr.3c01362}} Reviews 21 publications with data on Na2C2O4 solubility in 273-373 K. Linear approximation S (moles per kg of water) = a T + b where a = 0.00266, b = -0.521 , with sigma = 0.0079, R^2 = 0.984. At 25 C (298.15 K) S = 0.272 mol/kg. Sodium oxalate is less soluble than other alkali oxalates. In nature it is called natroxalate. Sodium oxalate is monoclinic with a P2/c space group. The oxalate ion is planar (D_{2h}) in the solid, twisted (D_{2d}) in solution. Also gives solubility of lithium, potassium, and cesium oxalates, in graph form: About 0.75 Li, 2.25 K, 8.85 Cs (Foote and Andrew dicarboxylic_acids_salts/ reynolds-et-al-2023-a-review-of-sodium-oxalate-solubility-in-water.pdf ---------------------------------------------------------------------- H. W. Foote, I. A. Andrew (1905): "The Acid Oxalates of Lithium, Sodium, Potassium and Caesium and Their Solubility". ''American Chemical Journal'', volume 34, issue , pages 153−164. {{doi|}} Cited by as giving solubilities of the dialkali oxalates as well as the acid ones. ---------------------------------------------------------------------- Hideyuki Suzuki, Hideaki Muratake (2014): "Functionalized oxatriquinanes and their structural equilibrium in protic solvent". ''Chemical and Pharmaceutical Bulletin'', volume 62, issue 9, pages 921-926. {{issn|1347-5223}} {{doi|10.1248/cpb.c14-00384}} Synthesis of acetyl-oxatriquinane hexafluorophosphate and acetyl-oxatriquinacene trifluoromethanesulfonate. Not interesting. ---------------------------------------------------------------------- Karl O. Christe, Carl J. Schack, Richard D. Wilson (1975): "Novel onium salts: Synthesis and characterization of oxonium hexafluoroantimonate ({{chem2|OH3+}}{{chem2|SbF6-}}) and oxonium hexafluoroarsenate ({{chem2|OH3+}}{{chem2|AsF6-}})". ''Inorganic Chemistry'', volume 14, issue 9, pages . {{doi|10.1021/ic50151a039}} As per the title. To make the hexafluoroantimonate (white solid), {{chem2|SbF5}} was dissolved in excess HF, then equimolar amount of H2O was added and excess HF was removed by vacuum at 25 C. White solid. For the hexafluoroarsenate, H2O was dissolved in excess HF and equimolar amount of {{chem2|AsF5}} was added and excess HF was removed by vacuum at 25 C. White solid. Also describes making {{chem2|OH3+}}{{chem2|BF4-}} by adding equimolar {{chem2|BF3}} to a solution of H2O in HF, then evaporating excess HF at -10 C. White solid that melts at 0 C to a liquid with 4 mmHg dissociation pressure at 22 C. ----------------------------------------------------------------------- Gorkem Gunbas, Nema Hafezi, William L. Sheppard, Marilyn M. Olmstead, Irini V. Stoyanova, Fook S. Tham, Matthew P. Meyer and Mark Mascal (2012): "Extreme oxatriquinanes and a record C–O bond length". ''Nature Chemistry'', volume 4, pages 1018-1023. {{doi|10.1038/NCHEM.1502}} Measures the C-O bond length of several derivatives of oxatriquinane, finds one (1,4,7-tri-''tert''-butyloxatriquinane with record bond length of 162.2 pm. oxonium/ gunbas-record-C-O-bond length-oxatriquinane.pdf ---------------------------------------------------------------------- Weng Fu, James Vaughan (2013): "Morphological Investigation of Sodium Oxalate Crystals Grown in Aqueous Sodium Hydroxide Solution". Chapter of ''Light Metals 2013'', pages 191–194. {{isbn|978-3-319-65135-4}} {{doi|10.1007/978-3-319-65136-1_34}} Creates a supersaturated solution of Na2C2O4 by saturating at 55 C and cooling to 20 C, then injects into NaOH solutions of various concentrations, and analyzes the shape of crystals formed. Notes significant step in the change of specific surface area between 3.33 mol/L and 5 mol/L. But there is no mention of checking whether the latter may be mixed crystals such as Na3.C2O4.OH. dicarboxylic_acids_salts/ wengfu-vaughan-effect-of-NaOH-on-crystal-shape-Na2C2O4.pdf --------------------------------------------------------------------- Shizuyoshi Sakai, Yoshihiro Kobayashi, Yoshio Ishii (1971): "Reaction of dialkyltin dialkoxides with carbon disulfide at higher temperature. Preparation of orthocarbonates". ''The Journal of Organic Chemistry'', volume 36, issue 9, pages 1176–1180. {{doi|10.1021/jo00808a002}} Obtains (spiro) orthocarbonates by reacting bis(tributyltin) alkene gycolate with carbon disulfide. --------------------------------------------------------------------- Jennifer Lowe, Mark Ogden, Anthony McKinnon, Gordon Parkinson (2002): "Crystal growth of sodium oxalate from aqueous solution". ''Journal of Crystal Growth'', volumes 237–239, part 1, pages 408-413. {{doi|10.1016/S0022-0248(01)01864-4}} Sodium oxalate has a monoclinic crystal structure and belongs to space group P21/a. The unit cell dimensions are a = 1037.5 b = 524.3, c = 344.9 \beta = 92.66. Saturated solutions were prepared at 55 C and evaporated over 48 h. Crystal surface was examined in situ, during growth (!) with atomic force microscope. Growth was seen to proceed by multiple steps with irregular edges. --------------------------------------------------------------------- Ashok Kumar, Raj Narain Mehrotra (1974): "Mechanism of oxidation of cyclohexanehexol (inositol) by quinquevalent vanadium". ''International Journal of Chemical Kinetics'', volume 6, issue 1, pages 15-28. {{doi|10.1002/kin.550060103}} Uses ammonium pentavanadate in water with sulfuric or perchloric acid. Solution has {{chem2|VO2+}} ions with vanadium in the +5 oxidation state. Oxidation of inositol with excess of this solution yielded a hydrazone derivative. Color of the vanadium solution darkens with addition of inositol, with average wavelength of absorption shifing from 391 nm to 399 nm. inositol/ kumar_mech_oxid_inositol.pdf --------------------------------------------------------------------- Richard Buchner, Faradj Samani, Peter M. May, Peter Sturm, Glenn Hefter (2003): "Hydration and Ion Pairing in Aqueous Sodium Oxalate Solutions". ''ChemPhysChem'', volume 4, issue 4, pages 373-378. {{doi|10.1002/cphc.200390064}} Sodium oxalate solutions have pairs of a Na+ and a C2O4-2 with a layer of water in between. dicarboxylic_acids_salts/ buchner_hydration_sodium_oxalate.pdf --------------------------------------------------------------------- Glenn Hefter, Andrew Tromans, Peter M. May, Erich Königsberger (2018): "Solubility of sodium oxalate in concentrated electrolyte solutions". ''Journal of Chemical Engineering Data'', volume 63, issue , pages 542−552. {{doi|}} Determines solubility of Na2C2O4 in solutions of NaCl, NaClO4, NaOH, KCl, KOH, Me4NCl, and LiCl of various concentrations. Salts of Na depress the solubility in accordance with the common ion effect, depending on the Na+ cconcentration and almost independent of the anion. Other salts yielded a small increase in solubility, except for Me4NCl, and LiCl that caused a notable decrease. Solid phase was always Na2C2O4. Solubility in pute water is 0.267 at 298.15 K, 0.325 at 323.15 K, 0.384 at 343.15 K (mol per L or water). dicarboxylic_acids_salts/ hefter-et-al-2018-solubility-of-sodium-oxalate-in-concentrated-electrolyte-solutions.pdf --------------------------------------------------------------------- Norma Barnes, Mónica Gramajo de Doz, Horacio N. Sólimo (1997): "Aqueous phase diagrams containing oxalic acid at 303.15 K". ''Fluid Phase Equilibria'', volume 134, issues 1–2, pages 201-211. {{doi|10.1016/S0378-3812(97)00035-6}} Ternary diagrams of water (WAT), anhydrous H2C2O4 (AOA), and a third compound (Y) at 303.15 K. The Y is 1-pentanol (POL), isobutyl acetate (IBA), and methyl isobutyl ketone (MIK). X forms a monohydrate (HOA) with 71.42% anhydrous oxalic acid and 28.58% water, the commercial form. Densities (kg/L) and melting points POL 815.2 IBA 873.l MIK 800.4 Melting points (K): AOA 460.4 HOA 375.3 WAT and POL are partly miscible (11% WAT in POL, 1.78% POL in WAT, wt frac at 30 C), so there is a region with 2 liquid phases, and one with 2 liquid phases plus HOA, with with the AOA split between the liquid phases. WAT and IBA diagram is similar, but since the two are very poorly miscible (1.18% WAT in IBA, 1.00% IBA in WAT) some of the regions are smaller. WAT and MIK diagram is mostly similar (1.78% WAT in MIK, 1.79% MIK in WAT), but there is a nonzero range of anydrous dicarboxylic_acids_salts/ barnes-oxalic-acid-three-phase-diagrams.pdf --------------------------------------------------------------------- Mark P. Thomas, Stephen J. Mills, and Barry V. L. Potter (2016): "The 'other' inositols and their phosphates: Synthesis, biology, and medicine (with recent advances in ''myo''-inositol chemistry)". ''Angewandte Chemie Reviews'', volume 55, pages 1614-1650. {{doi|10.1002/anie.201502227}} (international), {{doi|10.1002/ange.201502227}} (German) Neo and D-chiro phosphates were recently found in nature. AgranoffÏs turtle. Scyllo is relevant for neurodegenerative diseases and D-chiro for diabetes. Myo, muco, scyllo, epi, neo, allo, D-chiro, L-chiro occur in nature. Only cis is not known to occur. Methods of preparation. Cis is not accessibe from conduritol but can be obtained from myo-inositol by another route. --------------------------------------------------------------------- M. Mascal, N. Hafezi, N. K. Meher, J. C. Fettinger (2008): "Oxatriquinane and oxatriquinacene: extraordinary oxonium ions". ''Journal of the American Chemical Society'', volume 130, issue 41, pages 13532–13533. {{doi|10.1021/ja805686u}} Oxatriquinane, a fused, tricyclic alkyl oxonium ion of unprecented stability, was synthesized in five steps from 1,4,7-cyclononatriene. It survives reflux in H2O, chromatography, and attack by alcohols, alkyl thiols, halide ions, and hindered amine bases. The X-ray crystal structure shows longer C−O bond distances and more acute C−O−C bond angles than any reported alkyloxonium salt. The corresponding oxatriquinene and oxatriquinacene were also synthesized and represent the first examples of stable allyl oxonium species. Synthesized from cyclonona-1,4,7-triene. Has C-O bond lengths of 154 pm, C-O-C bond angles of 109.8 degrees. --------------------------------------------------------------------- Nema Hafezi (2010): [https://www.proquest.com/openview/f6f9820d0ba72a44c61c35c19c7ec27b/1 ''Synthesis and Characterization of Oxatriquinanes'']. Ph. D. thesis, University of California at Davis. UMI 3444022. Synthesized from cyclonona-1,4,7-triene. Has C-O bond lengths of 154 pm, C-O-C bond angles of 109.8 degrees. --------------------------------------------------------------------- (): "". '''', volume , issue , pages . {{doi|}} --------------------------------------------------------------------- (): "". '''', volume , issue , pages . {{doi|}} --------------------------------------------------------------------- (): "". '''', volume , issue , pages . {{doi|}} --------------------------------------------------------------------- (): "". 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