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Sodium naphthalene is an organic salt with the chemical formula Na + [C 10 H 8] −. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a solvate with ligands bound to Na +. [1]
Naphthalene: 217.9 78.2 –6.80 Nitrobenzene: 210.8 5.24 5.7 –7.00 Phenol: 181.75 3.60 43.0 –7.27 K f [2] K b [1] Water: 100.00 0.512 0.00 –1.86 K b & K f [2] Ethyl Acetate: 77.1 [5] Acetic Anhydride: 139.0 [6] Ethylene Dichloride: 1.25 83.5 −35 [7] Acetonitrile: 0.78 81.6 −45 [8] Heptane: 98.4 [9] Isobutanol: 107.7 [10] n-Hexane: 0. ...
With alkali metals, naphthalene forms the dark blue-green radical anion salts such as sodium naphthalene, Na + C 10 H − 8. The naphthalene anions are strong reducing agents. Naphthalene can be hydrogenated under high pressure in the presence of metal catalysts to give 1,2,3,4-tetrahydronaphthalene(C 10 H 12), also known as tetralin.
The fluorine-to-carbon atomic ratio (F/C ratio) is reduced from PTFE's theoretical ratio of 2.0 to 0.2 or less, after exposure to sodium naphthalene for 1 minute. [ 6 ] [ 7 ] [ 8 ] The fluorine atoms are replaced with hydroxyl, carbonyl, and other functional groups which can form hydrogen bonds.
[5] [6] In one of the breakthrough events in the field of polymer science, Szwarc elucidated that electron transfer occurred from radical anion sodium naphthalene to styrene. The results in the formation of an organosodium species, which rapidly added styrene to form a "two – ended living polymer."
Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. [1] [2] The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity.
Sodium atoms have 11 electrons, one more than the stable configuration of the noble gas neon. As a result, sodium usually forms ionic compounds involving the Na + cation. [1] Sodium is a reactive alkali metal and is much more stable in ionic compounds. It can also form intermetallic compounds and organosodium compounds.
Sodium is a chemical element; it has symbol Na (from Neo-Latin natrium) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable isotope is 23 Na. The free metal does not occur in nature and must be prepared from compounds.