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Title: Formation Mechanism and Possible Stereocontrol of Bisphenol A Derivatives: A Computational Study
Authors: Banerjee, Swastika
Periyasamy, Ganga
Pati, Swapan Kumar
Keywords: Physical Chemistry
Brominated Flame Retardants
Noncovalent Interactions
Thermochemical Kinetics
Density Functionals
Issue Date: 2014
Publisher: American Chemical Society
Citation: Banerjee, S; Periyasamy, G; Pati, SK, Formation Mechanism and Possible Stereocontrol of Bisphenol A Derivatives: A Computational Study. Journal of Physical Chemistry B 2014, 118 (31) 9258-9262,
Journal of Physical Chemistry B
Abstract: Density functional theoretical study elucidates two different pathways for metabolic activation of 2,2'-bis(4-hydroxyphenyl) propane (Bisphenol A; BPA) and consequential formation of 4-methyl-2,4-bis(p-hydroxyphenl)pent-2-ene (M-1) and 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (M-2, the potential environmental estrogen). Selectivity toward M-1(nontoxic)/M-2(toxic) formation can be controlled by varying the polarity of the reaction medium. We also found the reversal of thermodynamic stability for M-1/M-2 in response to the static polarization of the medium. Moreover, stereocontrol of biologically active M-2 with static polarization as the switch (similar to 0.005 au) might affect the receptor binding. This analysis may be useful in dictating the prevention of the harmful action of BPA and its metabolites.
Description: Restricted Access
ISSN: 1520-6106
Appears in Collections:Research Articles (Swapan Kumar Pati)

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