A theoretical investigation of the oxidation states of palladium complexes and their role in the carbonylation reaction

Molecular Physics

Volumn 108, Issue 12, 2010, Pages 1619-1640

  Bottoni, Andrea ^a   Carvajal, Maria Angels ^b   Miscione, Gian Pietro ^a   Novoa, Juan J ^c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

ab initio; computational chemistry; electronic structure; quantum chemistry

Indexed keywords

CARBONYLATION; CHLORINE; CHLORINE COMPOUNDS; COMPLEXATION; COMPUTATIONAL CHEMISTRY; COORDINATION REACTIONS; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; MOLECULES; PALLADIUM; PHOSPHORUS; PHOSPHORUS COMPOUNDS; QUANTUM CHEMISTRY; QUANTUM THEORY; SEMICONDUCTING INDIUM GALLIUM ARSENIDE; SPHERES;

AB INITIO; ALLYL CHLORIDES; ALLYL FRAGMENTS; CARBONYLATION REACTIONS; CO MOLECULE; COORDINATION SPHERE; EXOTHERMIC PROCESS; OXIDATION STATE; PALLADIUM COMPLEXES; PHOSPHINE COMPLEX; PHOSPHINE LIGANDS; PHOSPHOROUS ATOMS; REACTING SPECIES; REACTION PATHS; THEORETICAL INVESTIGATIONS;

PALLADIUM COMPOUNDS;

EID: 84962467325     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268976.2010.486139     Document Type: Article

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102. In order to verify the hypothesis that the reaction follows a pathway involving ionic species [11], we carried out PCM calculations on the two following systems: (a) PPh3(OAc)2+Pd(PPh3)2 (M7) and the alternative charged system (b) PPh3(OAc)(+)+ Pd(PPh3)2(OAc)(-) which would form in the case of an ionic pathway. The solvent emulated by the PCM calculations was nitromethane (=38.2). The computational results show that system (a) is 29.6 kcal mol-1 more stable than system (b). Also, we compared, in the same medium, the relative stability of PPh3(OAc)2 and PPh3(OAc)++(OAc)-. Even in this case the neutral system turns out to be more stable (by 6.4 kcal mol-1) than the charged system. These computational findings suggest that, at least for the present model, the mechanism proposed in our study seems to be favoured with respect to a reaction pathway involving ionic species. However, it is possible, even if unlikely if we consider the significant energy difference between systems (a) and (b), that the approximations of an implicit solvent model (such as PCM) affect this conclusion and that the employment of a larger model system (possibly with an explicit solvent description) may lead to different results.