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Insights into the free-energy dependence of intramolecular dissociative electron transfer (Articolo in rivista)

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Insights into the free-energy dependence of intramolecular dissociative electron transfer (Articolo in rivista) (literal)

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Antonello S., Crisma M., Formaggio F., Moretto A., Taddei F., Toniolo C., Maran F. (2002)
Insights into the free-energy dependence of intramolecular dissociative electron transfer
in Journal of the American Chemical Society (Print)
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Antonello S., Crisma M., Formaggio F., Moretto A., Taddei F., Toniolo C., Maran F. (literal)

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Impact factor 2002 della rivista: 6.201 Numero di citazioni al 7/07/2004: 10 (Fonte: ISI Web of Science). Questo lavoro ha costituito il punto di partenza per lo studio successivo di sistemi Donor-Spacer-Acceptor basati su peptidi elicoidali rigidi e del ruolo svolto dai legami a idrogeno nel processo di trasferimento elettronico intramolecolare. (literal)

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Pubblicazione su rivista scientifica Abstract: To study the relationship between rate and driving force of intramolecular dissociative electron transfer, a series of donor-spacer-acceptor systems (D-Sp-A) has been devised and synthesized. Cis-1-aminocyclohexane-4-carboxylic acid and a perester functional group were kept constant as the spacer and the acceptor, respectively, whereas unsubstituted or variously substituted phthalimide groups were selected as the donors. X-ray crystallography and ab inition conformational calculations pointed to D-Sp-A molecules having the cis-(cyclohexane) equatorial(phthalimido) - axial(perester) conformation and the same D/A orientation. The electrochemical analysis provided clear evidence of a concerted dissociative electron-trasfer mechanism. The intramolecular rate constants were determined and compared with the corresponding intermolecular values, the latter being obtained by using model molecules. (literal)

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(1) Dipartimento di Chimica Fisica, Università di Padova; (2) Istituto di Chimica Biomolecolare CNR, Sezione di Padova (Formaggio F. e Toniolo C. in qualità di ricercatori associati; Moretto A. personale in formazione); (3) Dipartimento di Chimica, Università di Modena e Reggio Emilia (literal)

Titolo

Insights into the free-energy dependence of intramolecular dissociative electron transfer (literal)

Abstract

To study the relationship between rate and driving force of intramolecular dissociative electron transfer, a series of donor-spacer-acceptor systems (D-Sp-A) has been devised and synthesized. Cis-1-aminocyclohexane-4-carboxylic acid and a perester functional group were kept constant as the spacer and the acceptor, respectively, whereas unsubstituted or variously substituted phthalimide groups were selected as the donors. X-ray crystallography and ab inition conformational calculations pointed to D-Sp-A molecules having the cis-(cyclohexane) equatorial(phthalimido) - axial(perester) conformation and the same D/A orientation. The electrochemical analysis provided clear evidence of a concerted dissociative electron-trasfer mechanism. The intramolecular rate constants were determined and compared with the corresponding intermolecular values, the latter being obtained by using model molecules. (literal)

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