Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process (Articolo in rivista) (literal)

Anno

• 2005-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1021/la048021k (literal)

Alternative label

• Hromadova, M; Pospisil, L; Fanelli, N; Giannarelli, S; (2005)
  Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process
  in Langmuir
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Hromadova, M; Pospisil, L; Fanelli, N; Giannarelli, S; (literal)

Pagina inizio

• 1923 (literal)

Pagina fine

• 1930 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 21 (literal)

Rivista

• Langmuir (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• J Heyrovsky Inst Phys Chem ASCR, CZ-18223 Prague, Czech Republic CNR, Ist Proc Chim Fis, I-56124 Pisa, Italy Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy (literal)

Titolo

• Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process (literal)

Abstract

• The reduction mechanism of the pesticide vinclozoline (3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3- oxazolidine-2,4-dione) was studied in nonaqueous solvents in the confined environment of a cyclodextrin(CD) cavity. The effect of the cavity dimensions on the mechanism of the redox process was evaluated using glucose as a reference and using three cyclodextrin molecules of different cavity sizes, namely, alfaCD, betaCD, and gammaCD. In the absence of CD the main reduction product of vinclozoline in the first reduction step is dichloroaniline. An addition of glucose leads to a quantitative change of mechanism with 10 products in total. Addition of CD, however, leads exclusively to dechlorination of the phenyl ring. The degree of dechlorination depends strongly on the choice of cyclodextrin molecule. The importance of the complex formation equilibria in the change of the mechanism is supported by a series of semiempirical AM1 quantum-mechanical calculations. Very good correlation (correlation coefficient 0.995) was obtained between the complex stabilization energy of the inclusion complex and the degree of pesticide dechlorination. Additionally, we were able to show that the complexes are stabilized by the formation of intermolecular hydrogen bonds between the host and guest species. CD molecules do not simply act as proton donors in a nonaqueous environment, but also protect parts of the molecule included within the cavity and steer the degradation process toward fewer products. (literal)

Prodotto di

• Istituto per i processi chimico-fisici (IPCF) (Istituto)
• Laboratorio di Chimica Analitica Strumentale (MD.P01.019.001) (Modulo)

Autore CNR

• NICOLANGELO FANELLI (Persona)

Insieme di parole chiave

• Keywords of "Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto per i processi chimico-fisici (IPCF) (Istituto)
• Laboratorio di Chimica Analitica Strumentale (MD.P01.019.001) (Modulo)

Autore CNR di

• NICOLANGELO FANELLI (Persona)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Langmuir (Rivista)

Insieme di parole chiave di

• Keywords of "Models of pesticides inside the cavities of molecular dimensions. A role of the guest inclusion in the dechlorination process" (Insieme di parole chiave)