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               222                                                                                  Halogen Chemistry


                 Very large chlorinated polymers also have special prop-  TROSCOPY • NUCLEAR MAGNETIC RESONANCE (NMR)
               erties which make them commercially valuable. The most  • ORGANIC CHEMISTRY,SYNTHESIS • PERIODIC TABLE
               important of these, the polyvinyl chlorides (PVCs), are  (CHEMISTRY) • POLLUTION,ENVIRONMENTAL
               used for electrical insulation, rubber substitutes (tub-
               ing, belting, and gaskets), and the production of water-
               resistant, artificial textiles.
                 Highly fluorinated molecules are very unreactive. Ex-  BIBLIOGRAPHY
               periments with small mammals have shown that blood can
               be entirely replaced by certain biochemically inert perflu-  Cotton, F. A., Wilkinson, G., Murillo, C. A., and Bochmann, M. (1999).
               oroorganics. Life is sustained by the fluorocarbon blood  “Advanced Inorganic Chemistry,” 6th ed., Wiley, New York.
               substitute, which has the ability to dissolve, transport, and  Cox, P. A. (1989). “The Elements: Their Origin, Abundance, and Distri-
               release oxygen by simple solubility. Experiments suggest  bution,” Oxford University Press, England.
                                                                 Das, K. V. (1997). “Main Group Elements and Their Compounds,”
               that there is no apparent ill effect, and the animal is subse-
                                                                   Springer-Verlag, New York.
               quently able to regenerate its own blood supply as the flu-  Davenport, J. W., and Wylie, D. M. (1996). “New Refrigerants for Air
               orocarbon is gradually exhaled through the lungs. Perfluo-  Conditioning and Refrigeration Systems,” Prentice Hall, Englewood
               rooctyl bromide (C 8 F 17 Br) is a nonirritating, radioopaque  Cliffs, NJ.
               material used for the X-ray inspection of organs.  Emsley, J. (1998). “The Elements,” 3rd ed., Oxford University Press,
                                                                   New York.
                 Small, lightly fluorinated molecules often exhibit toxic
                                                                 Fabian, P., and Singh, O. N., eds. (1999). “Reactive halogen compounds
               properties. Ethyl fluoroacetate and fluoroacetic acid were  in the atmosphere,” In “Handbook of Environmental Chemistry,” Vol.
               among the first nerve gases. Sodium monofluoroacetate is  4, part E., Springer-Verlag, New York.
               a rodenticide, and monofluoroacetamide has been used as  Greenwood, N. N., and Earnshaw, A. (1997). “Chemistry of the Ele-
                                                                   ments,” 2nd ed., Butterworth-Heinemann, Oxford, U.K.
               a systemic insecticide. Both are dangerous to humans.
                                                                 Hagen, A., ed. (1991). “Inorganic Reactions and Methods: The For-
                 The introduction of a single fluorine atom into biologi-
                                                                   mation of Bonds to Halogens (Part 2),” Vol. 4, VCH Publishers,
               cally significant molecules or established drugs frequently  New York.
               increases the efficacy of the drug or creates an enzyme-  “Kirk-Othmer Encyclopedia of Chemical Technology,” 4th ed., Vols. 2
               blocking agent. The compound 5–fluorouracil is thought  (1992), 5 (1993), 6 (1993), 11 (1994), and 14 (1995), Wiley, New
               to interfere with the biochemical operation of living cells  York.
                                                                 March, J. (1992). “Advanced Organic Chemistry: Reactions, Mecha-
               and has been used successfully in the treatment of some
                                                                   nisms, and Structure,” 4th ed., Wiley, New York.
               forms of cancer.                                  Olah, G. A., Prakash, G. K. S., and Chambers, R. D., eds. (1992). “Syn-
                                                                   thetic Fluorine Chemistry,” Wiley, New York.
                                                                 Perry, D. L., and Phillips, S. L., eds. (1995). “Handbook of Inorganic
               SEE ALSO THE FOLLOWING ARTICLES                     Compounds,” CRC Press, Boca Raton, FL.
                                                                 Rappoport, Z., Hudlicky, M., and Zupan, M. (1989). “The Formation of
                                                                   Carbon Halogen Bonds,” Wiley, New York.
               BONDING AND STRUCTURE IN SOLIDS • HYDROGEN        “Ullmann’s Encyclopedia of Industrial Inorganic Chemicals and Prod-
               BONDS • LIGAND FIELD CONCEPT • M ¨ OSSBAUER SPEC-   ucts” (1998). Vol. 6, Wiley, New York.
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