Guanidine-guanidinium Ccooperation in bifunctional artificial phosphodiesterases based on diphenylmethane spacers; gem- dialkyl effect on catalytic efficiency (Articolo in rivista)

Type
Label
  • Guanidine-guanidinium Ccooperation in bifunctional artificial phosphodiesterases based on diphenylmethane spacers; gem- dialkyl effect on catalytic efficiency (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo401085z (literal)
Alternative label
  • R. Salvio, L. Mandolini, C. Savelli (2013)
    Guanidine-guanidinium Ccooperation in bifunctional artificial phosphodiesterases based on diphenylmethane spacers; gem- dialkyl effect on catalytic efficiency
    in Journal of organic chemistry; American Chemical Society, Washington (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • R. Salvio, L. Mandolini, C. Savelli (literal)
Pagina inizio
  • 7259 (literal)
Pagina fine
  • 7263 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://pubs.acs.org/joc (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 78 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 5 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopus (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica and IMC-CNR Sezione Meccanismi di Reazione, Universita?La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy. (literal)
Titolo
  • Guanidine-guanidinium Ccooperation in bifunctional artificial phosphodiesterases based on diphenylmethane spacers; gem- dialkyl effect on catalytic efficiency (literal)
Abstract
  • Diphenylmethane derivatives 1-3, decorated with two guanidine units, are effective catalysts of HPNP transesterification. Substitution of the methylene group of the parent diphenylmethane spacer with cyclohexylidene and adamantylidene moieties enhances catalytic efficency, with gem-dialkyl effect accelerations of 4.5 and 9.1, respectively. Activation parameters and DFT calculations of the rotational barriers around the C-Ar bonds indicate that a major contribution to the driving force for enhanced catalysis is entropic in nature. (literal)
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