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001 ocn919448280;

003 OCoLC;

005 20160202100009.0;

006 m o d ;

007 cr bn|||||||||;

008 150831s2015 ncua ob 000 0 eng d;

035 a| (Sirsi) o919448280;

035 a| (OCoLC)919448280;

049 a| EREE;

090 a| QD181.P8;

100 1 a| Carroll, Jeffrey Samuel,e| author.?| UNAUTHORIZED;

245 10 a| Investigation into the scope, limitations, and mechanistic aspects of a regioselective acylation of cycloplatinated complexes /c| by Jeffrey Samuel Carroll.;

264 1 a| [Greenville, N.C.] :b| [East Carolina University],c| 2015.;

300 a| 115 pages :b| illustrations (some color);

336 a| textb| txt2| rdacontent;

337 a| computerb| c2| rdamedia;

338 a| online resourceb| cr2| rdacarrier;

347 a| text fileb| PDFc| 6.71Mb2| rda;

538 a| System requirements: Adobe Reader.;

538 a| Mode of access: World Wide Web.;

502 b| M.S.c| East Carolina Universityd| 2015.;

500 a| Presented to the faculty of the Department of Chemistry.;

500 a| Advisor: Shouquan Huo.;

500 a| Title from PDF t.p. (viewed September 23, 2015).;

520 3 a| In the reaction of N-isopropyl-N-phenyl-2,2'-bipyridin-6-amine with potassium tetrachloroplatinate, the selective C-H bond activation was complicated by the low selectivity of sp² C-H bond activation in acetonitrile and low yield of sp³ C-H activation in acetic acid. The product resulting from the highly selective sp³ activation was collected in low yield due to competing side reactions. Following C[superscript]iPr-N bond dissociation, the platinum complex (2a, X = NH, R = H) was regioselectively acylated. It was later discovered that 2a could be regioselectively acylated by reacting with acetic anhydride in acetic acid. Furthermore, the acylated platinum complex (3a, X = NH, R = H) was also prepared in a cascade intramolecular cycloplatination-acylation reaction by reacting the organic ligand (1a, X = NH, R = H) with potassium tetrachloroplatinate in a mixture of acetic acid and acetic anhydride. A series of ligands with structural modifications have been designed, synthesized, cycloplatinated, and acylated to investigate the scope of this reaction, and to shed light on the mechanism of the acylation. The reaction showed great tolerance to various linker groups (X), as well as many electron donating/withdrawing groups (R) on the phenyl ring. Reaction conditions were optimized and a variety of solvents were useful in this reaction, including acetonitrile, benzonitrile, and 1,2-dichloroethane. Alternate electrophiles such as benzoyl chloride were also useful in the acylation reaction. Experimental results of the acylation reaction of a library of substrates (2) will be reported, and the mechanistic implications of these results will be discussed.;

504 a| Includes bibliographical references.;

650 0 a| Platinum compoundsx| Structure.=| ^A827427;

650 0 a| Hydrogen bonding.=| ^A61304;

650 0 a| Carbon.=| ^A47375;

650 0 a| Chemical bonds.=| ^A5651;

653 a| Chemistry;

653 a| Organic chemistry;

653 a| Inorganic chemistry;

653 a| Acylation;

653 a| Cyclometalation;

653 a| Functionalization;

653 a| Platinum complex;

700 1 a| Huo, Shouquan,e| degree supervisor.?| UNAUTHORIZED;

710 2 a| East Carolina University.b| Department of Chemistry.?| UNAUTHORIZED;

856 40 z| Access via ScholarShipu| http://hdl.handle.net/10342/5047;

949 o| jgml;

994 a| C0b| ERE;

596 a| 1 4;

998 a| 3808137;

999 a| CLICK ON WEB ADDRESSw| ASISc| 1i| 3808137-1001l| JNETm| JOYNERr| Ys| Yt| JNE3ETDu| 8/31/2015x| ETDz| JERESOURCE;

999 a| CLICK ON WEB ADDRESSw| ASISc| 1i| 3808137-2001l| HSLELECm| HSLr| Ys| Yt| HEETDu| 8/31/2015x| ETDz| HERESOURCE;

Investigation into the scope, limitations, and mechanistic aspects of a regioselective acylation of cycloplatinated complexes / by Jeffrey Samuel Carroll.

Author/creator	Carroll, Jeffrey Samuel author.
Other author	Huo, Shouquan, degree supervisor.
Other author	East Carolina University. Department of Chemistry.
Format	Theses and dissertations
Publication	[Greenville, N.C.] : [East Carolina University], 2015.
Description	115 pages : illustrations (some color)
Supplemental Content	Access via ScholarShip
Subjects	Platinum compounds--Structure. Hydrogen bonding. Carbon. Chemical bonds.

Summary	In the reaction of N-isopropyl-N-phenyl-2,2'-bipyridin-6-amine with potassium tetrachloroplatinate, the selective C-H bond activation was complicated by the low selectivity of sp² C-H bond activation in acetonitrile and low yield of sp³ C-H activation in acetic acid. The product resulting from the highly selective sp³ activation was collected in low yield due to competing side reactions. Following C[superscript]iPr-N bond dissociation, the platinum complex (2a, X = NH, R = H) was regioselectively acylated. It was later discovered that 2a could be regioselectively acylated by reacting with acetic anhydride in acetic acid. Furthermore, the acylated platinum complex (3a, X = NH, R = H) was also prepared in a cascade intramolecular cycloplatination-acylation reaction by reacting the organic ligand (1a, X = NH, R = H) with potassium tetrachloroplatinate in a mixture of acetic acid and acetic anhydride. A series of ligands with structural modifications have been designed, synthesized, cycloplatinated, and acylated to investigate the scope of this reaction, and to shed light on the mechanism of the acylation. The reaction showed great tolerance to various linker groups (X), as well as many electron donating/withdrawing groups (R) on the phenyl ring. Reaction conditions were optimized and a variety of solvents were useful in this reaction, including acetonitrile, benzonitrile, and 1,2-dichloroethane. Alternate electrophiles such as benzoyl chloride were also useful in the acylation reaction. Experimental results of the acylation reaction of a library of substrates (2) will be reported, and the mechanistic implications of these results will be discussed.
General note	Presented to the faculty of the Department of Chemistry.
General note	Advisor: Shouquan Huo.
General note	Title from PDF t.p. (viewed September 23, 2015).
Dissertation note	M.S. East Carolina University 2015.
Bibliography note	Includes bibliographical references.
Technical details	System requirements: Adobe Reader.
Technical details	Mode of access: World Wide Web.

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Investigation into the scope, limitations, and mechanistic aspects of a regioselective acylation of cycloplatinated complexes / by Jeffrey Samuel Carroll.

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