Gomberg was able to distinguish this compound from triphenylmethane (elemental analysis was not an option given the small differences in the hydrogen fractions of 6.29% and 6.60%) by nitration of 5 with nitric acid to 6. A strong base would be able to abstract the methine proton of the nitrated triphenylmethyl compound if present, forming a strongly colored compound.
Gomberg's success in synthesizing tetraphenylmethane set him on the attempt to prepare the next homologue hexaphenylethane, which led him to the discovery of the triphenylmethyl radical.
^Robbins, A.; Jeffrey, G. A.; Chesick, J. P.; Donohue, J.; Cotton, F. A.; Frenz, B. A.; Murillo, C. A. (1975-10-01). "A refinement of the crystal structure of tetraphenylmethane: three independent redeterminations". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 31 (10): 2395–2399. doi:10.1107/S0567740875007686. ISSN 0567-7408.
^Gomberg, M. (1898). "On tetraphenylmethane". J. Am. Chem. Soc.20 (10): 773–780. doi:10.1021/ja02072a009.
December 01, 2023
tetraphenylmethane, organic, compound, consisting, methane, core, with, four, phenyl, substituents, first, synthesized, moses, gomberg, 1898, namespreferred, iupac, name, methanetetrayltetrabenzeneidentifierscas, number, model, jsmol, interactive, imagechemspi. Tetraphenylmethane is an organic compound consisting of a methane core with four phenyl substituents It was first synthesized by Moses Gomberg in 1898 Tetraphenylmethane NamesPreferred IUPAC name 1 1 1 1 MethanetetrayltetrabenzeneIdentifiersCAS Number 630 76 2 Y3D model JSmol Interactive imageChemSpider 11917 YECHA InfoCard 100 010 132EC Number 211 144 0PubChem CID 12424UNII CM2Q9C446P YCompTox Dashboard EPA DTXSID30212215InChI InChI 1S C25H20 c1 5 13 21 14 6 1 25 22 15 7 2 8 16 22 23 17 9 3 10 18 23 24 19 11 4 12 20 24 h1 20H YKey PEQHIRFAKIASBK UHFFFAOYSA N YInChI 1 C25H20 c1 5 13 21 14 6 1 25 22 15 7 2 8 16 22 23 17 9 3 10 18 23 24 19 11 4 12 20 24 h1 20HKey PEQHIRFAKIASBK UHFFFAOYASSMILES c1ccccc1C c2ccccc2 c3ccccc3 c4ccccc4PropertiesChemical formula C25H20Molar mass 320 44 g molMelting point 282 C 540 F 555 K Boiling point 431 CStructure 1 Crystal structure tetragonalSpace group P4 21c No 114Point group S4Lattice constant a 10 896 A c 7 280 A 20 C Formula units Z 2HazardsGHS labelling PictogramsSignal word DangerHazard statements H350Precautionary statements P201 P202 P281 P308 P313 P405 P501Except 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 referencesSynthesis editGomberg s classical organic synthesis shown below starts by reacting triphenylmethyl bromide 1 with phenylhydrazine 2 to the hydrazine 3 Oxidation with nitrous acid then produces the azo compound 4 from which on heating above the melting point nitrogen gas evolves with formation of tetraphenylmethane 5 2 nbsp Gomberg was able to distinguish this compound from triphenylmethane elemental analysis was not an option given the small differences in the hydrogen fractions of 6 29 and 6 60 by nitration of 5 with nitric acid to 6 A strong base would be able to abstract the methine proton of the nitrated triphenylmethyl compound if present forming a strongly colored compound He obtained further evidence for the formation of tetraphenylmethane by reducing the nitro groups to amino groups with zinc dust in acetic acid to the leuco dye 7 which on exposure to hydrochloric acid eliminates aniline to the known compound pararosaniline 8 Gomberg s success in synthesizing tetraphenylmethane set him on the attempt to prepare the next homologue hexaphenylethane which led him to the discovery of the triphenylmethyl radical See also editTetraphenylborate Triphenylmethane TolueneReferences edit Robbins A Jeffrey G A Chesick J P Donohue J Cotton F A Frenz B A Murillo C A 1975 10 01 A refinement of the crystal structure of tetraphenylmethane three independent redeterminations Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 31 10 2395 2399 doi 10 1107 S0567740875007686 ISSN 0567 7408 Gomberg M 1898 On tetraphenylmethane J Am Chem Soc 20 10 773 780 doi 10 1021 ja02072a009 Retrieved from https en wikipedia org w index php title Tetraphenylmethane amp oldid 1186924582, wikipedia, wiki, book, books, library,
