Energetics of C−Cl, C−Br, and C−I Bonds in Haloacetic Acids: Enthalpies of Formation of XCH2COOH (X=Cl, Br, I) Compounds and the Carboxymethyl Radical

Lagoa, Ana L. C.; Diogo, Hermı́nio P.; Dias, M. Pilar; Piedade, Manuel E. Minas da; Amaral, Luı́sa M.P.F.; Silva, Manuel A.V. Ribeiro da; Simões, José A. Martinho; Guedes, Rita C.; Cabral, Benedito J. Costa; Schwarz, Karsten; Epple, Matthias

doi:10.1002/1521-3765(20010119)7:2<483::aid-chem483>3.3.co;2-1

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“…33,[41][42][43][44] As mentioned in the Experimental Section, the combustion calorimetric experiments on polyglycolide were made using a sample with empirical formula C 2.000 H 2.160 O 2.032 Cl 0.009243 -Na 0.004404 . The deficiency of Na versus Cl, and the excess of H and O versus C contents observed in this formula result form the partial hydrolysis of the polymer endgroups.…”

Section: Resultsmentioning

confidence: 88%

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Driving Force for the Thermally Induced Solid State Polymerization of Alkali Metal Halogenoacetates: A Thermochemical Analysis

Lagoa¹,

Diogo²,

Piedade³

et al. 2002

J. Phys. Chem. B

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Reaction-solution calorimetry was used to determine the standard molar enthalpies of formation of a series of lithium and sodium halogenoacetates in the crystalline state at 298.15 K. The obtained values were as follows: 740.9 ( 0.7) kJ‚mol -1 , ∆ f H°m(BrCH 2 COONa, cr) ) -(700.2 ( 1.2) kJ‚mol -1 , and ∆ f H°m(ICH 2 COONa, cr) ) -(642.0 ( 1.6) kJ‚mol -1 . Microcombustion calorimetric studies of a polyglycolide sample with the empirical formula C 2.000 H 2.160 O 2.032 Cl 0.009243 Na 0.004404 (PGA) led to ∆ f H°m(PGA, pol) ) -( 379.1 ( 1.1) kJ‚mol -1 . These results were used to discuss the energetics of the solid-state polymerization of alkali metal halogenoacetates leading to polyglycolide. In agreement with experimental observations, it is concluded that for a given metal, the reaction becomes less favorable when the halogen changes along the series Cl f Br f I. The reaction is also considerably less favorable for the lithium than for the homologue sodium salts. These differences in reactivity seem to be mainly determined by the lattice enthalpy of the alkali metal halide salt formed in each reaction.

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Section: Resultsmentioning

confidence: 88%

“…The enthalpies of solution of chloroacetic acid in the various calorimetric solutions were measured using a sample whose preparation and purification have been described. 33 Combustion Calorimetry. Details of the micro combustion calorimetric apparatus and the general experimental procedure have been reported.…”

Section: Methodsmentioning

confidence: 99%