Bromochlorofluoromethane

In this article we will explore Bromochlorofluoromethane from different perspectives, delving into its importance, impact and relevance in different areas. Bromochlorofluoromethane is a topic that has captured the attention of experts and enthusiasts, generating debate and reflection around its implications. Throughout these pages, we will analyze the key aspects of Bromochlorofluoromethane, from its history to its evolution today, including its influence on society and its future projection. Through interviews, analysis and testimonies, we aim to shed light on Bromochlorofluoromethane and offer the reader a complete and enriching vision of this topic that is so relevant today. Join us on this exciting journey through the universe of Bromochlorofluoromethane!

Bromochlorofluoromethane
Left: (S)-Bromochlorofluoromethane
Right: (R)-Bromochlorofluoromethane
Names
Preferred IUPAC name
Bromo(chloro)fluoromethane
Other names
Bromochlorofluoromethane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CHBrClF/c2-1(3)4/h1H checkY
    Key: YNKZSBSRKWVMEZ-UHFFFAOYSA-N checkY
  • C(F)(Cl)Br
Properties
CHBrClF
Molar mass 147.37 g·mol−1
Density 1.953 g/cm3
Melting point −115 °C; −175 °F; 158 K
Boiling point 36 °C; 97 °F; 309 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Bromochlorofluoromethane or fluorochlorobromomethane, is a chemical compound and trihalomethane derivative with the chemical formula CHBrClF. As one of the simplest possible stable chiral compounds, it is useful for fundamental research into this area of chemistry.[1] However, its relative instability to hydrolysis,[2] and lack of suitable functional groups, made separation of the enantiomers of bromochlorofluoromethane especially challenging,[3] and this was not accomplished until almost a century after it was first synthesised, in March 2005, though it has now been done by a variety of methods.[4][5][6][7] More recent research using bromochlorofluoromethane has focused on its potential use for experimental measurement of parity violation, a major unsolved problem in quantum physics.[8][9][10] For example, the S enantiomer is predicted to be lower in energy by about 2.356×10−16 eV (56.97 mHz),[11] and the frequency of the C−F vibrational mode should be about 2.4 mHz lower for the R-enantiomer.[10]

See also

References

  1. ^ Berry, Kenneth L.; Sturtevant, Julian M. (1942). "Fluorochlorobromomethane". Journal of the American Chemical Society. 64 (7): 1599–1600. Bibcode:1942JAChS..64.1599B. doi:10.1021/ja01259a031.
  2. ^ Thomas L. Gilchrist. Comprehensive Organic Functional Group Transformations. Volume 6. Synthesis: Carbon with Three or Four Attached Heteroatoms. p228. Pergamon / Elsevier, 1995. ISBN 0-08-042704-9
  3. ^ Hargreaves, Michael K.; Modarai, Borzoo (1969). "An optically active haloform: (+)-bromochlorofluoromethane". Journal of the Chemical Society D: Chemical Communications. 1: 16. doi:10.1039/C29690000016.
  4. ^ Canceill, Josette; Lacombe, Liliane; Collet, Andre (1985). "Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made cryptophane and determination of its maximum rotation". Journal of the American Chemical Society. 107 (24): 6993–6996. Bibcode:1985JAChS.107.6993C. doi:10.1021/ja00310a041.
  5. ^ Doyle, Thomas R.; Vogl, Otto (1989). "Bromochlorofluoromethane and deuteriobromochlorofluoromethane of high optical purity". Journal of the American Chemical Society. 111 (22): 8510–8511. Bibcode:1989JAChS.111.8510D. doi:10.1021/ja00204a029.
  6. ^ Grosenick, Heiko; Schurig, Volker; Costante, Jeanne; Collet, André (1995). "Gas chromatographic enantiomer separation of bromochlorofluoromethane". Tetrahedron: Asymmetry. 6 (1): 87–88. doi:10.1016/0957-4166(94)00358-I.
  7. ^ Pitzer, M.; Kunitski, M.; Johnson, A. S.; Jahnke, T.; Sann, H.; Sturm, F.; Schmidt, L. P. H.; Schmidt-Bocking, H.; Dorner, R.; Stohner, J.; Kiedrowski, J.; Reggelin, M.; Marquardt, S.; Schiesser, A.; Berger, R.; Schoffler, M. S. (2013). "Direct Determination of Absolute Molecular Stereochemistry in Gas Phase by Coulomb Explosion Imaging" (PDF). Science. 341 (6150): 1096–1100. Bibcode:2013Sci...341.1096P. doi:10.1126/science.1240362. PMID 24009390. S2CID 206549826.
  8. ^ Crassous, J.; Collet, A. (2000). "The bromochlorofluoromethane saga". Enantiomer. 5 (5): 429–438. PMID 11143807.
  9. ^ Crassous, Jeanne; Monier, Franck; Dutasta, Jean-Pierre; Ziskind, Michaël; Daussy, Christophe; Grain, Christophe; Chardonnet, Christian (2003). "Search for Resolution of Chiral Fluorohalogenomethanes and Parity-Violation Effects at the Molecular Level". ChemPhysChem. 4 (6): 541–548. doi:10.1002/cphc.200200536. PMID 12836475.
  10. ^ a b Darquié, Benoît; Stoeffler, Clara; Shelkovnikov, Alexander; Daussy, Christophe; Amy-Klein, Anne; Chardonnet, Christian; Zrig, Samia; Guy, Laure; Crassous, Jeanne; Soulard, Pascale; Asselin, Pierre; Huet, Thérèse R.; Schwerdtfeger, Peter; Bast, Radovan; Saue, Trond (2010). "Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy". Chirality. 22 (10): 870–884. arXiv:1007.3352. doi:10.1002/chir.20911. PMID 20839292. S2CID 2722847.
  11. ^ Quack, Martin; Seyfang, Georg; Wichmann, Gunther (2022). "Perspectives on parity violation in chiral molecules: theory, spectroscopic experiment and biomolecular homochirality". Chemical Science. 13 (36): 10598–10643. doi:10.1039/d2sc01323a. hdl:20.500.11850/569820. PMC 9491092. PMID 36320700.


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