Heptachlorepoxides: Theoretical versus experimental study of the embedded samples in the matrixes of organic crystals

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 76, Issue 3-4, 2013, Pages 415-426

  Ivanova, Bojidarka ^a   Spiteller, Michael ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Crystallography; Heptachlorepoxides; Mass spectrometry; Optical spectroscopy; Quantum chemistry

Indexed keywords

EID: 84880137319     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0213-x     Document Type: Article

References (56)

1. Murano, H., Otani, T., Makino, T., Seike, N., Sakai, M.: Effects of the application of carbonaceous adsorbents on pumpkin (Cucurbita maxima) uptake of heptachlor epoxide in soil. Soil Sci. Plant Nutr. 55, 325-332 (2009)
2. Prado, G., Bhalli, J., Marcos, R.: Genotoxicity of heptachlor and heptachlor epoxide in human TK6 lymphoblastoid cells. Mutat. Res. 673, 87-91 (2009)
3. Fenoglioa, C., Grossoa, A., Boncompagnia, E., Gandinib, C., Milanesia, M., Barnia, S.: Exposure to heptachlor: evaluation of the effects on the larval and adult epidermis of Rana kl. Esculenta Aquat. Toxicol. 91, 151-160 (2009)
4. Hwang, J., Kim, J., Kang, S.: Heptachlor induced PD-related neurotoxicity via mitochondrial damage in vitro and in vivo. J. Neurochem. 110(Suppl. 2), 167-210 (2011)
5. Tan, L., Qi, S., Zhang, J. Modified diatomite as adsorbent for removal of heptachlor from water. In: Abstracts of papers of the American Chemical Society, pp. 621-625 (2011)
6. Magnarelli, G., Souza, M., de D'Angelo, R.: Heptachlor and o-p′-DDT effects on protein kinase activities associated with human placenta particulate fractions. J. Biochem. Mol. Toxicol. 23, 185-192 (2009)
7. Longnecker, M.: Invited commentary:why DDT matters now. Am. J. Epidemiol. 162, 726-728 (2005)
8. Thomas, G., Wilkinson, M., Hodson, S., Jones, K.: Organohalogen chemicals in human blood from the United Kingdom. Environ. Pollut. 141, 30-41 (2006)
9. Cassidy, R., Natarajan, S., Vaughan, G.: The link between the insecticide heptachlor epoxide, estradiol, and breast cancer. Breast Cancer Res. Treat. 90, 55-64 (2005)
10. Bahadir, M., Parlar, H., Spiteller, M.: Springer Umweltlexikon, 2nd edn, pp. 1-1455. Springer, Berlin (2000)
11. Spiteller, M., Monkiedje, A., Bester, K.: Enantioselective degradation of pesticides in soil. Lecture in SETAC Europe 12th Annual Meeting, 12-16. May (2002)
12. Hartmann, H., Burhenne, J., Müller, K., Frede, H., Spiteller, M.: Rapid target analysis of pesticides in water by online coated capillary microextraction combined with liquid chromatography and tandem mass spectrometry. J. AOAC Int. 83, 762-770 (2000)
13. Klaus, F., Pfeifer, T., Spiteller, M.: APCI-MS/MS: a powerful tool for the analysis of bound residues resulting from the interaction pesticides with DOM and humic substances. Environ. Sci. Technol. 34, 3514-3520 (2000)
14. Fischer, P., Burhenne, J., Bach, M., Spiteller, M., Frede, H.: Diffuse Einträge von Pflanzenschutzmitteln in ein kleines Fließgewässer (Non-point contamination of small watershed by pesticides. Nachrichtenbl. Deut. Pflanzenschutzd. 50, 204-208 (1998)
15. Hartmann, H., Burhenne, J., Spiteller, M.: Trace determination of pesticides in water by coated capillary micro extraction (CCME) and reversed-phase high performance liquid chromatography. Fresenius Environ. Bull. 7, 096-103 (1998)
16. Hellpointner, E., Fritz, R., Scholz, K., Spiteller, M.: Lysimeter studies relevant to the fate of pesticides in the soil - experimental limitations/conclusions, BCPC Mono. Lysimeter Stud. Pestic. Soil 53, 141-144 (1992)
17. Ivanova, B., Spiteller, M.: Quantitative solid-state Raman spectroscopic method for control of fungicides. Analyst 137, 3355-3364 (2012)
18. Flamini, R., Panighel, A.: Mass spectrometry in grape and whine chemistry. Mass Spectrom. Rev. 25, 741-774 (2006)
19. Stemmler, E., Hites, E.: Methane enhanced negative ion mass spectra of hexachlorocyclopentadiene derivatives. Anal. Chem. 57, 684-692 (1985)
20. Buser, H., Miiller, M.: Enantiomer separation of chlordane components and metabolites using chiral high-resolution gas chromatography and detection by mass spectrometric techniques. Anal. Chem. 84, 3160-3175 (1992)
21. Korfmacher, W., Rushing, L., Siitonen, P., Branscomb, C., Holder, C.: Confirmation of heptachlor epoxide and octachlor epoxide in milk via fused silica gas chromatography/negative ion chemical ionization mass spectrometry. J. High Resolut. Chromatogr. Chromatogr. Commun. 1987, 332-336 (1987)
22. Biros, F., Doughert, R., Dalton, J.: Positive chemical ionization mass spectra of polycyclic halogenated pesticides. Org. Mass Spectrom. 6, 1161-1169 (1972)
23. Blessing, R.: An empirical correction for absorption anisotropy. Acta Crystallogr. A A51, 33-38 (1995)
24. Sheldrick, G.M.: A short history of SHELX. Acta Crystallogr. A A64, 112-122 (2008)
25. Sheldrick, G.M.: Experimental phasing with SHELXC/D/E: combining chain tracing with density modification. Acta Crysallogr. D66, 479-485 (2010)
26. Sheldrick, G.M.: Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr. A A46, 467-473 (1990)
27. Spek, A.: Single-crystal structure validation with the program PLATON. J. Appl. Crystallogr. 36, 7-13 (2003)
28. Ivanova, B., Spiteller, M.: On the chemical identification and determination of flavonoids in solid state. Talanta 94, 9-21 (2012)
29. Herebian, D., Zühlke, S., Lamshöft, M., Spiteller, M.: Multi-mycotoxin analysis in complex biological matrices using LC-ESI/MS: experimental study using triple stage quadrupole and linear ion trap-orbitrap. J. Sep. Sci. 32, 939-948 (2009)
30. Frisch, M., et al.: Gaussian 09. Gaussian, Inc., Pittsburgh (2009)
31. Quantum chemical Program Package; http://www.daltonprogram.org/download. html
32. Crawford, D.: Ab initio calculation of molecular chiroptical properties. Theor. Chem. Acc. 115, 227-245 (2006)
33. De Proft, F., Geerlings, P.: Conceptual and computational DFT in the study of aromaticity. Chem. Rev. 101, 1451-1464 (2001)
34. Grimme, S., Bahlmann, A., Haufe, G.: Ab initio calculations for the optical rotations of conformationally flexible molecules: a case study on six-, seven-, and eight-membered fluorinated cycloalkanol esters. Chirality 14, 793-797 (2002)
35. Grimme, S., Neese, F.: Double-hybrid density functional theory for excited electronic states of molecules. J. Chem. Phys. 127, 154116 (2007)
36. Ivanova, B., Spiteller, M.: Conformations and properties of the l-tryptophyl-containing peptides in solution, depending on the pH - theoretical study vs. experiments. Biopolymers 93, 727-734 (2010)
37. Mennucci, B., Tomasi, J., Cammi, R., Cheeseman, J., Frisch, M., Devlin, F., Gabriel, S., Stephens, P.: Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J. Phys. Chem. A 106, 6102-6113 (2002)
38. Stephens, P., McCann, D., Cheeseman, J., Frisch, M.: Determination of absolute configurations of chiral molecules using ab initio time-dependent density functional theory calculations of optical rotation: how reliable are absolute configurations obtained for molecules with small rotations? Chirality 17, S52-S64 (2005)
39. Stephens, S., Devlin, F., Cheeseman, J., Frisch, M., Bortolini, O., Besse, P.: Determination of absolute configuration using ab initio calculation of optical rotation. Chirality 15, S57-S64 (2003)
40. Yhao, Y., Truhlar, D.: Density functionals with broad applicability in chemistry. Acc. Chem. Res. 41, 157-167 (2008)
41. Zhao, Y., Truhlar, D.: The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215-241 (2008)
42. Office Program Package; http://de.openoffice.org/
43. Kelley, C.: Iterative methods for optimization, SIAM frontiers in applied mathematics, vol 18. SIAM, Philadelphia (1999)
44. Madsen, K., Nielsen, H., Tingleff, O.: Informatics and mathematical modelling, 2nd edn. DTU Press, Lyngby (2004)
45. Cornett, D., Reyzer, M., Chaurand, Caprioli, R.: MALDI imaging mass spectrometry: molecular snapshots of biochemical systems. Nat. Methods 4, 826-828 (2007)
46. Esquenazi, E., Yang, Y., Watrous, J., Gerwickac, W., Dorrestein, P.: Imaging mass spectrometry of natural products. Nat. Prod. Rep. 26, 1521-1529 (2009)
47. Sinha, T., Khatib-Shahidi, S., Yankeelov, T., Mapara, K., Ehtesham, M., Cornett, D., Dawant, D., Caprioli, R., Gore, J.: Integrating spatially resolved three-dimensional MALDI IMS with in vivo magnetic resonance imaging. Nat. Methods 5, 57-64 (2008)
48. Gross, J.: Mass spectrometry: a textbook, 2nd edn, pp. 1-753. Springer Verlag, Heidelberg (2000)
49. Biemann, K.: Mass spectrometry: organic chemical application, pp. 1-370. McGraw-Hill Book Company Inc., New York (1962)
50. Cole, R. (ed.): Electrospray and MALDI mass spectrometry, 2nd edn, pp. 1-847. Wiley, Hoboken (2010)
51. Cole, R. (ed.): Electrospray ionization mass spectrometry, pp. 1-577. Wiley, New York (1997)
52. Cochranaen, W., Forbes, M.: Isomerization sf 8-exo-4,5,6,9,8,8- hegtachloro-2,3-ertalo-epoxy-3a,4,7,7a-tetrahydro-4,7-methanoindain with base. Can. J. Chem. 49, 3569-3571 (1983)
53. Trathnigg, A., Junek, H.: Alkoholyse aromatischer carbons/iureester. Monatshefte fiir Chemie 115, 1185-1197 (1984)
54. Nakatsugawa, T., Ishodata, M., Dahm, P.: Microsomal epoxidation of cyclodiene insecticides. Biochem. Pharmacol. 14, 1853-1865 (1965)
55. Brooksa, G., Harrison, G., Lewis, S.: Cyclodiene epoxide ring hydration by mycrosome from mammalian liver and houseflies. Biochem. Pharmacol. 19, 255-273 (1970)
56. Alling, G., Fredericks, P.: Positive halogen compounds. IV. Radical reactions of chlorine and t-butyl hypochlorite with some small ring compounds. J. Am. Chem. Soc. 84, 3326-3331 (1962)