calixarenes and catechol

calixarenes has been researched along with catechol* in 1 studies

Other Studies

1 other study(ies) available for calixarenes and catechol

ArticleYear
Structures and thermodynamics of biphenyl dihydrodiol stereoisomers and their metabolites in the enzymatic degradation of arene xenobiotics.
    Journal of computational chemistry, 2009, Nov-30, Volume: 30, Issue:15

    A key step in the metabolic degradation of biphenyl xenobiotics is catechol formation upon dehydrogenation of cis- and trans-dihydrodiols in prokaryotic and eukaryotic pathways, respectively. Structure and thermodynamics of stereoisomers of cis-, trans-2,3-biphenyl-dihydrodiols (I) and their dehydrogenation products (hydroxyketones, II), as well as final catechol (2,3-biphenyldiol, III) are studied by means of ab initio MP2/6-311++G(2df,2p)//MP2/6-311G(d,p) calculations. Formation of stereoisomers I and II is exothermic and endergonic, whereas III is enthalpically and entropically driven. Dehydrogenations are endothermic (DeltaHR0 approximately 1.5-4 kcal mol(-1)) and exergonic (DeltaGR0 approximately -5 to -7.5 kcal mol(-1)) without noticeable differences between cis and trans pathways, although the same keto stereoisomer II-(2S) is found to be the more favored product from both cis- and trans-I. The final II --> III tautomerization is thermodynamically enhanced (DeltaHR0 approximately -27, DeltaGR0 approximately -28 kcal mol(-1)) but the process is shown to have a large activation energy if it had to occur via unimolecular path. Although this tautomerization is generally assumed to be a nonenzymatic process as it involves rearomatization of an oxygenated ring, proton transfer with an anionic intermediate might be a more probable process.

    Topics: 2,2'-Dipyridyl; Calixarenes; Catechols; Computer Simulation; Dioxygenases; Models, Chemical; Molecular Structure; Naphthalenes; Quantum Theory; Stereoisomerism; Thermodynamics; Xenobiotics

2009