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Synthesis, structure, and solution p...

Smith, Gary Lee Nunnery.

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Synthesis, structure, and solution properties of benzoannelated cryptands.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Synthesis, structure, and solution properties of benzoannelated cryptands./
Author:	Smith, Gary Lee Nunnery.
Description:	249 p.
Notes:	Source: Dissertation Abstracts International, Volume: 67-01, Section: B, page: 0239.
Contained By:	Dissertation Abstracts International67-01B.
Subject:	Chemistry, Analytical. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3206115
ISBN:	9780542521737

Synthesis, structure, and solution properties of benzoannelated cryptands.
Smith, Gary Lee Nunnery.

Synthesis, structure, and solution properties of benzoannelated cryptands. - 249 p.

Source: Dissertation Abstracts International, Volume: 67-01, Section: B, page: 0239.

Thesis (Ph.D.)--The University of Oklahoma, 2006.

Macrobicyclic ligands, cryptands, with alkyl nitrogen bridgehead atoms form stable complexes with a wide variety of metal ions. Cryptands 2.2.1 and 2.2.2 have an inherent selectivity for the toxic heavy metals cadmium and lead over important biological cations such as sodium, potassium, and calcium. However, the basicity of the alkyl nitrogen atoms results in significant interference due to protonation reactions in the physiological pH range. To minimize this problem several cryptands were synthesized with aniline (An) nitrogen bridgehead atoms.

ISBN: 9780542521737Subjects--Topical Terms:

586156
Chemistry, Analytical.

Synthesis, structure, and solution properties of benzoannelated cryptands.
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100 1 $a Smith, Gary Lee Nunnery. $3 1916485
245 1 0 $a Synthesis, structure, and solution properties of benzoannelated cryptands.
300 $a 249 p.
500 $a Source: Dissertation Abstracts International, Volume: 67-01, Section: B, page: 0239.
500 $a Adviser: Richard W. Taylor.
502 $a Thesis (Ph.D.)--The University of Oklahoma, 2006.
520 $a Macrobicyclic ligands, cryptands, with alkyl nitrogen bridgehead atoms form stable complexes with a wide variety of metal ions. Cryptands 2.2.1 and 2.2.2 have an inherent selectivity for the toxic heavy metals cadmium and lead over important biological cations such as sodium, potassium, and calcium. However, the basicity of the alkyl nitrogen atoms results in significant interference due to protonation reactions in the physiological pH range. To minimize this problem several cryptands were synthesized with aniline (An) nitrogen bridgehead atoms.
520 $a Cryptands An2.2.1 and An2.2.2 were synthesized by high dilution techniques. Attempts to produce An3.1.1 gave primarily the 2 + 2 addition product An3.1.1.3. X-ray crystallography, ESI-MS, and NMR techniques were used to characterize the synthesized cryptands and monocyclic intermediates. The solid-state structures of cryptates An2.2.2.K+·ClO4-. An2.2.2-Pb2+·(NCS-)2, and 2.2B.2B·Pb2+·NCS - were determined and confirmed that the metal ions were located inside the cavity of the macrobicyclic ligand. Protonation constants for An2.2.1 and An2.2.2 are greater than 2.5 pH units below the parent compounds 2.2.1, 2.2.2, and 2.2B.2B. The stepwise protonation constants in water are log KH1 = 5.4, log KH2 = 3.1 for An2.2.1 and log KH1 = 5.3, log KH2 = 3.4 for An2.2.2. The metal formation constants for cryptands An2.2.1 and An2.2.2 are all weaker in comparison to the parent cryptands 2.2.1, 2.2.2, and 2.2B.2B. The metal formation constants (log KML) in water for An2.2.2 with Pb 2+, Cd2+, Ba2+, Sr2+, Ca2+, Na+, and K+ are 8.5, 3.0, 4.7, 4.1, 2.7, 2.4, and 2.0, respectively. The metal formation constants (log KML) in water for An2.2.1 with Pb2+, Cd2+ , Ba2+, Sr2+, Ca2+, Na +, and K+ are 5.0, 4.0, 3.6, 4.2, 4.3, 4.1, and 3.7, respectively. The inherent selectivity of the parent cryptands for lead over the biological cations sodium, potassium, and calcium is present for An2.2.2, but not for An2.2.1.
590 $a School code: 0169.
650 4 $a Chemistry, Analytical. $3 586156
650 4 $a Chemistry, Inorganic. $3 517253
650 4 $a Chemistry, Organic. $3 516206
690 $a 0486
690 $a 0488
690 $a 0490
710 2 0 $a The University of Oklahoma. $3 1021915
773 0 $t Dissertation Abstracts International $g 67-01B.
790 1 0 $a Taylor, Richard W., $e advisor
790 $a 0169
791 $a Ph.D.
792 $a 2006
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3206115