Multiple functional group cooperation in phosphate diester cleavage promoted by Zn(II) complexes

Chemical Communications

Volumn , Issue 24, 2004, Pages 2862-2863

  Livieri, Monica ^a   Mancin, Fabrizio ^a   Tonellato, Umberto ^a   Chin, Jik ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE; ZINC;

ARTICLE; COMPLEX FORMATION; ENZYME KINETICS; HYDROGEN BOND; HYDROLYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 11244284859     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412111b     Document Type: Article

References (19)

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10. For other examples of hydrolytic agents based on the cooperation between metal ions and organic functional groups see ref. 2c.
11. J. C. Mareque-Rivas, R. Prabaharan and R. Torres Martin de Rosales, Chem. Commun., 2004, 76.
12. As pointed out by one of the referees, the possibility of the presence of major and minor ionization states for the mono-deprotonated species will need to be investigated. If the observed reactivity arises for a minor state, true second order rate constants could be substantially greater that those reported in Table 2.
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14. Intracomplex hydrogen bonds in complexes containing the 6-aminopyridine subunit have been reported and shown to increase both the acidity of metal-bound water molecule (Lewis acid activation) and the binding of phosphate anions: J. Chin, S. Chung and D. H. Kim, J. Am. Chem. Soc., 2002, 124, 10948; J. C. Mareque-Rivas, R. Torres Martin de Rosales and S. Parsons, Chem. Commun, 2004, 610.
15. Intracomplex hydrogen bonds in complexes containing the 6-aminopyridine subunit have been reported and shown to increase both the acidity of metal-bound water molecule (Lewis acid activation) and the binding of phosphate anions: J. Chin, S. Chung and D. H. Kim, J. Am. Chem. Soc., 2002, 124, 10948; J. C. Mareque-Rivas, R. Torres Martin de Rosales and S. Parsons, Chem. Commun, 2004, 610.
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19. In the presence of an excess of substrate and for prolonged reaction times, the NMR analysis indicated that with L2-Zn(II) the transesterification process is followed by a slower cleavage of BNP leading to the formation of p-nitrophenyl phosphate, probably due to the activation of a hydrolytic mechanism similar to that of L3·Zn(II).