Structure and isomerization of alpha-phenylcinnamic acid stereoisomers - reaction pathway and transition-state structure by semiempirical methods

Tasi, Gyula and Pálinkó, István and Körtvélyesi, Tamás (1997) Structure and isomerization of alpha-phenylcinnamic acid stereoisomers - reaction pathway and transition-state structure by semiempirical methods. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 391 (1-2). pp. 189-192. ISSN 0166-1280

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Abstract

The isomerization reaction of E- and Z-alpha-phenylcinnamic acid molecules was studied at the level of semiempirical quantum chemical methods (MNDO, AM1 and PM3). Calculations revealed that Z-alpha-phenylcinnamic acid is slightly more stable than the E isomer. The activation enthalpy for isomerization and the transition-state structure were also determined. The difference in the acidities of the mio stereoisomers of alpha-phenylcinnamic acid and cinnamic acid (this is the basis of their separation experimentally) was rationalized by computing the dipole moments of the ions.

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