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Synthesis of superbase and correlation between gas phase acidity and pKa study of ionic liquid

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Title
Synthesis of superbase and correlation between gas phase acidity and pKa study of ionic liquid
Name (type = personal)
NamePart (type = family)
Chu
NamePart (type = given)
Pingcheng
NamePart (type = date)
1989-
DisplayForm
PINGCHENG CHU
Role
RoleTerm (authority = RULIB)
author
Name (type = personal)
NamePart (type = family)
Lee
NamePart (type = given)
Jeehiun Katherine
DisplayForm
Jeehiun Katherine Lee
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
chair
Name (type = personal)
NamePart (type = family)
Krogh-Jespersen
NamePart (type = given)
Karsten
DisplayForm
Karsten Krogh-Jespersen
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Warmuth
NamePart (type = given)
Ralf
DisplayForm
Ralf Warmuth
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB)
degree grantor
Name (type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm (authority = RULIB)
school
TypeOfResource
Text
Genre (authority = marcgt)
theses
OriginInfo
DateCreated (qualifier = exact)
2013
DateOther (qualifier = exact); (type = degree)
2013-10
Place
PlaceTerm (type = code)
xx
Language
LanguageTerm (authority = ISO639-2b); (type = code)
eng
Abstract (type = abstract)
Since chemical reactions involving proton transfer as a key mechanism step become prevalent, development of Brønsted bases has been the intense focus in terms of catalyzing proton transfer reactions. Lambert et al. found and confirmed one cyclopropenimine as a strong superbase by measuring its pKa in acetonitrile for the first time. Based on that, we calculated several cyclopropenimine’s proton affinity (PA) which are much higher than all the volatile reference superbases we’ve ever used. It means that if we could obtain those very basic superbases, they would be used as reference bases to bracket PAs of highly basic compounds. Herein, we tried to design and synthesize cyclopropenimine-based superbases and investigated their tunability of PA by modifying various electron withdrawing and donating groups. The corresponding calculation results are consistent with our proposal that cyclopropenimine superbase with EWG decrease PA while EDG increase PA. We also tried to measure PA of one cyclopropenimine superbase that we synthesized by Cooks kinetics method. The other project focuses on a special class of ionic liquid which is known as green solvent with several advantages over traditional organic solvent. This new type of ionic liquid is imidazolium-based ionic liquid with tunable aryl and alkyl substituents which was designed by Strassner et al.. They named this category of ionic liquid as tunable aryl-alkyl ionic liquids (TAAILs). The reason we are interested in them is looking into the correlation between TAAILs’ aqueous property and their theoretical acidity in gas phase and solution. If there was some correlation, we could predict imidazolium compounds’ pKa’s by their gas phase property. Based upon this conjecture, we measured different TAAILs’ acidity by LCQ bracketing method on mass spectrometry, calculated their free energy in solution phase as well as in gas phase and developed two methods to measure their pKa’s in solution. Their acidity results demonstrate that those TAAILs with electron-withdrawing groups on para-position of phenyl substituent have high acidity while other TAAILs with electron-donating para-substituent have low acidity. Besides, I successfully obtained the pKa value of one TAAILs as 25.4 in water via H/D exchange kinetics experiment on NMR.
Subject (authority = RUETD)
Topic
Chemistry and Chemical Biology
RelatedItem (type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier (type = RULIB)
ETD
Identifier
ETD_5001
PhysicalDescription
Form (authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
xi, 82 p. : ill.
Note (type = degree)
M.S.
Note (type = bibliography)
Includes bibliographical references
Note (type = vita)
Includes vita
Note (type = statement of responsibility)
by Pingcheng Chu
Subject (authority = ETD-LCSH)
Topic
Ionic solutions
Subject (authority = ETD-LCSH)
Topic
Protons
RelatedItem (type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier (type = local)
rucore19991600001
Location
PhysicalLocation (authority = marcorg); (displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier (type = doi)
doi:10.7282/T3445JHZ
Genre (authority = ExL-Esploro)
ETD graduate
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RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
CHU
GivenName
PINGCHENG
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2013-09-17 00:32:54
AssociatedEntity
Name
PINGCHENG CHU
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
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Type
License
Name
Author Agreement License
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I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
Copyright
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Copyright protected
Availability
Status
Open
Reason
Permission or license
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ContentModel
ETD
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windows xp
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