Reactivity of mucohalic acids in water

Water Research

Volumn 45, Issue 2, 2011, Pages 714-720

  Gómez Bombarelli, Rafael ^a   González Pérez, Marina ^a   Calle, Emilio ^a   Casado, Julio ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Chlorination by products; Mucobromic acid; Mucochloric acid; MX

Indexed keywords

BYPRODUCTS; CHLORINATION; HYDRATES; POTABLE WATER; REACTION INTERMEDIATES;

CHLORINATION BYPRODUCTS; DISINFECTION BY-PRODUCT; DISINFECTION BYPRODUCTS; GENOTOXINS; HALOGENATED FURANONES; MUCOBROMIC ACIDS; MUCOCHLORIC; MUCOCHLORIC ACID; MUCOHALIC; MX;

HYDRATION;

ADENOSINE; CARCINOGEN; CYTOSINE; DNA BASE; FURANONE DERIVATIVE; GUANOSINE; HYDROXIDE; ION; MUCOBROMIC ACID; MUCOHALIC ACID; TAP WATER; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; CHEMICAL ANALYSIS; DECOMPOSITION; DISINFECTION; DRINKING WATER; ORGANIC ACID; PH; REACTION KINETICS; REACTIVATION;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); DECOMPOSITION; ELECTROPHILICITY; EQUILIBRIUM CONSTANT; HYDRATION; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 78650416481     PISSN: 00431354     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.watres.2010.08.040     Document Type: Article

References (49)

1. Asplund D., Kronberg L., Sjöholm R., Munter T. Reaction of mucochloric acid with adenosine - formation of 8-(N-6-Adenosinyl) Ethenoadenosine derivatives. Chem. Res. Toxicol. 1995, 8(6):841-846.
2. Baxter N.J., Rigoreau L.J.M., Laws A.P., Page M.I. Reactivity and mechanism in the hydrolysis of β-Sultams. J. Am. Chem. Soc. 2000, 122(14):3375-3385.
3. Bell R.P. Adv. Phys. Org. Chem. 1966, 4:1-29.
4. Biechler S.S., Taft R.W. The effect of structure on kinetics and mechanism of the alkaline hydrolysis of anilides. J. Am. Chem. Soc. 1957, 79:4927-4935.
5. Bright G.R., Fisher G.W., Rogowska J., Taylor D.L. Fluorescence ratio imaging microscopy: temporal and spatial measuments of cytoplasmic pH.J. Cell Biol. 1987, 104(4):1019-1044.
6. Daniel F.B., DeAngelo A.B., Stober J.A., Olson G.R., Page N.P. Hepatocarcinogenicity of chloral hydrate, 2-chloroacetaldehyde, and dichloroacetic acid in the male B6C3F1 mouse. Fundam. Appl. Toxicol. 1992, 19(2):159-168.
7. Fekadu K., Parzefall W., Kronberg L., Franzen R., Schulte-Hermann R., Knasmuller S. Induction of genotoxic effects by chlorohydroxifuranones, byproducts of water disinfection, in E. coli K-12 cells recovered from various organs of mice. Environ. Mol. Mutagen 1994, 24:317-324.
8. Franzen R., Tanabe K., Morita M. Ring-chain tautomerism of chlorinated hydroxyfuranones and reaction with nucleosides. Chemosphere 1999, 38(5):973-980.
9. Frisch M.J., et al. Gaussian 03, Revision B.05 2003, Gaussian, Inc, Pittsburgh, PA.
10. GEMStat United Nations Global Environment Monitoring System Water Programme, Global Water Quality Data and Statistics 2010, http://www.gemstat.org.
11. Gómez-Bombarelli R., González-Pérez M., Pérez-Prior M.T., Calle E., Casado J. Computational calculation of equilibrium constants: addition to carbonyl compounds. J. Phys. Chem. A 2009, 113:11423-11428.
12. Greenzaid P., Luz Z., Samuel D. A nuclear magnetic resonance study of the reversible hydration of aliphatic aldehydes and ketones. I. Oxygen-17 and proton spectra and equilibrium constants. J. Am. Chem. Soc. 1967, 89(4):749-756.
13. Haselkorn T., Whittemore A.S., Udaltsova N., Friedman G.D. Short-term chloral hydrate administration and cancer in humans. Drug Saf. 2006, 29(1):67-77.
14. Hilal S.H., Bornander L.L., Carreira L.A. Hydration equilibrium constants of aldehydes, ketones and quinazolines. QSAR Comb. Sci. 2005, 24(5):631-638.
15. Ho J.M., Coote M.L. A universal approach for continuum solvent pK(a) calculations: are we there yet?. Theor. Chem. Acc. 2010, 125(1-2):3-21.
16. Hooper D.L. Nuclear magnetic resonance measurements of equilibria involving hydration and hemiacetal formation from some carbonyl compounds. J. Chem. Soc. B-Physical Org. 1967, 3:169-170.
17. IARC, 2004. Some Drinking-water Disinfectants and Contaminants, Including Arsenic, Lyon, France.
18. Jansson K., Hyttinen J., Niittykoski M., Mäki-Paakkanen J. Mutagenicity in vitro of 3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid), a chlorine disinfection by-product in drinkingwater. Environ. Mol. Mutagen. 1995, 25:284-287.
19. Kanniganti R., Johnson J.D., Ball L.M., Charles M.J. Identification of compounds in mutagenic extracts of aqueous monochloraminated fulvic-acid. Environ. Sci. Technol. 1992, 26(10):1998-2004.
20. King J.F., GIll M.S., Klassen D.F. Mechanisms of reactions of sulfonyl compounds with nucleophiles in protic media. Pure Appl. Chem. 1996, 68(4):825-830.
21. Klika K.D., Mäki J., Sjöholm R., Kronberg L. Regioisomeric Alpha-Hydroxy Chlorohydrins From The Reaction Of Mucochloric Acid And Guanosine 2006, Arkivoc, pp. 65-74.
22. Knasmuller S., Zohrer E., Kronberg L., Kundi M., Franzen R., SchulteHermann R. Mutational spectra of salmonella typhimurium revertants induced by chlorohydroxyfuranones, byproducts of chlorine disinfection of drinking water. Chem. Res. Toxicol. 1996, 9(2):374-381.
23. Krasner S.S., Weinberg H.S., Richardson S.D., Pastor S.J., Chinn R., Sclimenti M.J., Onstad G.D., Thruston A.D.J. Occurrence of a new generation of disinfection byproducts. Environ. Sci. Technol. 2006, 40(23):7175-7185.
24. Kronberg L., Asplund D., Mäki J., Sjöholm R. Reaction of mucochloric and mucobromic acids with adenosine and cytidine: formation of chloro- and bromopropenal derivatives. Chem. Res. Toxicol. 1996, 9(8):1257-1263.
25. Kronberg L., Christman R.F., Singh R., Ball L. Environ. Sci. Technol. 1991, 25:99.
26. Kronberg L., Franzen R. Environ. Sci. Technol. 1993, 27:1181.
27. Kronberg L., Holmbom B., Reunanen M., Tikkanen L. Identification and quantification of the Ames mutagenic compound 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and its geometric isomer E-2-chloro-4-(dichloromethyl)-4-oxobutenoic acid in chlorine-trated humic water and drinking water extracts. Environ. Sci. Technol. 1988, 22:1097-1103.
28. Kronberg L., Karlsson S., Sjöholm R. Formation of ethenocarbaldehyde derivatives of adenosine and cytidine in reactions with mucochloric acid. Chem. Res. Toxicol. 1993, 6(4):495-499.
29. Kronberg L., Sjöholm R., Karlsson S. Formation of 3, N(4)-Ethenocytidine, 1, N(6)-Ethenoadenosine, and 1, N(2)-Ethenoguanosine in reactions of mucochloric acid with nucleosides. Chem. Res. Toxicol. 1992, 5(6):852-855.
30. LeCurieux F., Munter T., Kronberg L. Identification of adenine adducts formed in reaction of calf thymus DNA with mutagenic chlorohydroxyfuranones found in drinking water. Chem. Res. Toxicol. 1997, 10(10):1180-1185.
31. Liviac D., Creus A., Marcos R. Genotoxicity analysis of two hydroxyfuranones, byproducts of water disinfection, in human cells treated in vitro. Environ. Mol. Mutagen 2009, 50(5):413-420.
32. Mäki J., Sjöholm R., Kronberg L. Formation of oxalo-substituted etheno derivatives in reactions of mucochloric acid with adenosine, guanosine and cytidine. J. Chem. Soc. Perkin Trans. 1999, 1(20):2923-2928.
33. McDonald T.A., Komulainen H. Environ. Sci. Heal 2005, 23:163.
34. Meier J.R., Knohl R.B., Coleman W.E., Ringhand H.P., Munch J.W., Kaylor W.H. Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and of its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. Mutat. Res. 1988, 206:177-182.
35. Menger F.M., Donohue J.A. Base-catalyzed hydrolysis of N-Acylpyrroles. A measurable acidity of a steady-state tetrahedral intermediate. J. Am. Chem. Soc. 1973, 95(2):432-437.
36. Mowry D.T. Mucochloric acid .1. Reactions of the pseudo acid group. J. Am. Chem. Soc. 1950, 72(6):2535-2537.
37. Mowry D.T. Mucochloric acid .2. Reactions of the aldehyde group. J. Am. Chem. Soc. 1953, 75(8):1909-1910.
38. Ono M., Todoriki R., Mitake A., Yukawa M., Goto Y., Tamura S. A kinetic study of alkaline hydrolysis of β-Arylaminoacrolein. Chem. Pharm. Bull. 1989, 37(11):2902-2908.
39. Onstad G.D., Weinberg H.S., Krasner S.S. Occurrence of halogenated furanones in U.S. Drinking waters. Environ. Sci. Technol. 2008, 42(9):3341-3348.
40. Page M.I. β-Sultams - mechanism of reactions and use as inhibitors of serine proteases. Acc. Chem. Res. 2004, 37(5):297-303.
41. Pollack R.M., Bender M.L. The Alkaline hydrolysis of p-Nitroacetanilide and p-Formylacetanilide. J. Am. Chem. Soc. 1970, 92(24):7190-7194.
42. Richardson S.D., Plewa M.J., Wagner E.D., Schoeny R., DeMarini D.M. Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research. Mutat. Res. 2007, 636(1-3):178-242.
43. Ross A., Boron W. Intracellular pH. Physiol. Rev. 1981, 2:296-434.
44. Salmon A.G., Kizer K.W., Zeise L., Jackson R.J., Smith M.T. Potential carcinogenicity of chloral hydrate - a review. J. Toxicol. Clin. Toxicol. 1995, 33(2):115-121.
45. Seng J.E., Agrawal N., Horsley E.T.M., Leakey T.I., Scherer E.M., Xia S.J., Allaben W.T., Leakey J.E.A. Toxicokinetics of chloral hydrate in ad libitum-fed, dietary-controlled, and calorically restricted male B6C3F(1) mice following short-term exposure. Toxicol. Appl. Pharmacol. 2003, 193(2):281-292.
46. Smeds A., Vartianinen T.M.-P., Mäki-Paakkanen J., Kronberg L. Concentrations of Ames mutagenic chlorohydroxyfuranones and related compounds in drinking waters. Environ. Sci. Technol. 1997, 31(4):1033-1039.
47. Us-Cfr, US Code of Federal Regulations. Title 40, vol. 19, Chapter I, Part 143.1-4 (2002).
48. Wasserman H.H., Precopio F.M. Studies on the mucohalic acids .1. The structure of mucoxychloric acid. J. Am. Chem. Soc. 1952, 74(2):326-328.
49. Wasserman H.H., Precopio F.M. Studies on the mucohalic acids .4. Replacement of halogen in the pseudo ester series. J. Am. Chem. Soc. 1954, 76(5):1242-1243.