Acetaminophen Radicals - Revision history

Wfox: /* Hyperfine Coupling Constants */

2021-04-16T15:35:03Z

Hyperfine Coupling Constants

2021-04-16T15:33:20Z

ΔHf Calculations

2021-04-16T15:29:42Z

Hyperfine Coupling Constants

2021-04-16T15:27:29Z

B3YLP/6-311+G(2d,p)

2021-04-16T15:26:56Z

B3YLP/6-311+G(2d,p)

2021-04-15T21:53:55Z

Cites

2021-04-15T21:53:16Z

Background

2021-04-15T21:52:30Z

Cites

2021-04-15T21:49:33Z

Cites

2021-04-15T21:49:08Z

Cites

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 {| class="wikitable"
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-! Phenoxy
+! Phenoxy (G)
 |-
 | 2.04

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 Below are the calculations of the ΔH<sub>f</sub> for the formation of a radical of the phenoxyl in acetaminophen. The values listed in  Hartree were found doing geometry optimizations using B3LYP/6-311+G(2d,p) basis sets.
 :ΔH<sub>rxn</sub> = ΔH<sub>f</sub>(Products) - ΔH<sub>f</sub>(Reactants)
-:ΔH<sub>rxn</sub> = ΔH<sub>f</sub>(-OH•) - H<sub>f</sub>(-OH)
+:ΔH<sub>rxn</sub> = ΔH<sub>f</sub>[(-OH•) + (H+)]- H<sub>f</sub>(-OH)
-:ΔH<sub>rxn</sub> = (-515.01158420 Hartree) - (-515.480291398 Hartree)
+:ΔH<sub>rxn</sub> = (-515.01158420 + -0.08303 Hartree) - (-515.480291398 Hartree)
-:ΔH<sub>rxn</sub> = 0.468707198 Hartree = 1230.59084209 kJ/mol
+:ΔH<sub>rxn</sub> = 0.385677198 Hartree =  1012.59556048 kJ/mol
 ==Citation==

← Older revision		Revision as of 15:29, 16 April 2021
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	===Hyperfine Coupling Constants===		===Hyperfine Coupling Constants===
		+	These were the constants used to generate the simulated ESR data above in WINSIM. These were found in the raw data output from the geometry optimization of the acetaminophen radical under "Isotropic Fermi Contact Couplings."

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 |[[File:Pchem_APAP_WINSIM.png|400px|WINSIM ESR Simulation|thumb|left|WINSIM ESR simulation showing the evidence of a radical on the molecule]]
 |}
 {| class="wikitable"

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 |[[File:Pchem_APAP_WINSIM.png|400px|WINSIM ESR Simulation|thumb|left|WINSIM ESR simulation showing the evidence of a radical on the molecule]]
 |}

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 :ΔH<sub>rxn</sub> = 0.468707198 Hartree = 1230.59084209 kJ/mol
-==Cites==
+==Citation==
 .) Hinson, Jack A., Dean W. Roberts, and Laura P. James. "Mechanisms of Acetaminophen-Induced Liver Necrosis." Handbook of Experimental Pharmacology Adverse Drug Reactions (2009): 369-405. Web.

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 The Ab-initio computation of the acetaminophen radical. The goal of this project is to elucidate where electrons are located on the molecule when a radicalization occurs.
 ==Background==
-Acetaminophen(APAP) is an active ingredient in many over-the-counter and prescription painkillers, such as Tylenol and Oxycodone. APAP is also responsible for approximately 50% of the cases of acute liver-failure in the United States and Great Britain. Treatments for acetaminophen-induced liver injury(AILI) are limited. The current mechanism for AILI is the production of hepatotoxic NAPQI as a metabolite in an enzymatic, two-electron oxidation. However, evidence also supports a one electron oxidation.
+Acetaminophen(APAP) is an active ingredient in many over-the-counter and prescription painkillers, such as Tylenol and Oxycodone. APAP is also responsible for approximately 50% of the cases of acute liver-failure in the United States and Great Britain (1). Treatments for acetaminophen-induced liver injury(AILI) are limited. The current mechanism for AILI is the production of hepatotoxic NAPQI as a metabolite in an enzymatic, two-electron oxidation (1). However, evidence also supports a one electron oxidation (2).
 ==Web MO/Gaussian==

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 ==Cites==
 This paper has ESR data on the acetaminophen radical
 * https://ehp.niehs.nih.gov/doi/pdf/10.1289/ehp.8564127

← Older revision		Revision as of 21:49, 15 April 2021
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	==Cites==		==Cites==
		+	This paper has ESR data on the acetaminophen radical
	https://ehp.niehs.nih.gov/doi/pdf/10.1289/ehp.8564127		https://ehp.niehs.nih.gov/doi/pdf/10.1289/ehp.8564127