supporting information for: structural and s group … supporting information for: structural and...

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SupportingInformationfor:

StructuralandSubstituentGroupEffectsonMultielectronStandardReductionPotentialsofAromatic

N-heterocycles

MitchellC.Groenenboom,1KarthikeyanSaravanan,1YaqunZhu,1JeffreyM.Carr,1AudeMarjolin,1

GabrielG.Faura,2EricC.Yu,2RaymondN.Dominey,2JohnA.Keith1,*

1DepartmentofChemicalandPetroleumEngineering,UniversityofPittsburgh,Pittsburgh,Pennsylvania

15261,UnitedStates

2DepartmentofChemistry,UniversityofRichmond,Richmond,Virginia23173

TableS1.EnergydifferencesbetweenB3LYP/ACCD//B3LYP/6-31+G*andB3LYP/ACCD//B3LYP/ACCD

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Asseenin

TableS1,thedifferencesinenergiesbetweenB3LYP/ACCD//B3LYP/6-31+G*and

B3LYP/ACCD//B3LYP/ACCDareminimal.

Table1.SubstituentgroupeffectsonabsolutepKasandredoxpotential

PourbaixDiagrams

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FigureS1.Quinolinepourbaixdiagram

FigureS2.2-quinolinepourbaixdiagram

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FigureS3.1,2-diazinepourbaixdiagram

FigureS4.1,3-diazinepourbaixdiagram

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FigureS5.1.4-diazinepourbaixdiagram

FigureS6.1,4-naphthyridinepourbaixdiagram

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FigureS7.1,6-naphthyridinepourbaixdiagram

FigureS8.1,8-naphthyridinepourbaixdiagram

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FigureS9.Phenanthrolinepourbaixdiagram

FigureS10.2,2’-bipyridinepourbaixdiagram

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FigureS11.4,4’-bipyridinepourbaixdiagram

FigureS12.4-Cl-quinolinepourbaixdiagram

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FigureS13.Pteridinepourbaixdiagram

FigureS14.Adeninepourbaixdiagram

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FigureS15.Purinepourbaixdiagram

FigureS16.Benzimidazolepourbaixdiagram

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FigureS17.4-CN-quinolinePourbaixdiagram

FigureS18.MercaptopridinePourbaixdiagram

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FigureS19.2-picolinePourbaixdiagram

FigureS20.3-picolinePourbaixdiagram

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FigureS21.4-picolinePourbaixdiagram

FigureS22.2,6-lutadinePourbaixdiagram

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FigureS23.2,5-lutidinePourbaixdiagram

FigureS24.4-aminopyridinePourbaixdiagram

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FigureS25.N,N-dimethyl-4-aminopyridine

FigureS26.NicotinamidePourbaixdiagram

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FigureS27.4-acetylquinolinePourbaixdiagram