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Stereochemical Studies of Nitrosamines: The Induced Circular Dichroism of Achiral Nitrosasmines

The induced circular dichroism (ICD) of several chiral nitrosamines and various chiral reagents has been investigated. The interaction is attributed to a 1:1 hydrogen bonded complex between the NO group of the nitrosamine and the hydroxyl groups of alcohols and polyols, or the amino group of amines. Only those chiral reagents possessing large differences in size of the groups about the hydrogen bonding site contributed to CD anomalies. The acyclic 2-octanols did not give observable Cotton effects, presumably due to the similarity in size of the methyl and methylene groups and rotational freedom of the acyclic system. The signs of the Cotton effects could be correlated with the absolute configuration of the sterically hindered alcohols and amines. Only the alpha, axial hydrogens of conformationally biased, heterocyclic nitrosamines were found to undergo selective hydrogen-deuterium exchange, suggesting that this feature is critical for nitrosamine carcinogenicity.

Identiferoai:union.ndltd.org:unt.edu/info:ark/67531/metadc331744
Date08 1900
CreatorsFribush, Howard M.
ContributorsLyle, Robert E., Marshall, James L., Jacobson, Myron, Jones, Paul R.
PublisherNorth Texas State University
Source SetsUniversity of North Texas
LanguageEnglish
Detected LanguageEnglish
TypeThesis or Dissertation
Formatix, 184 leaves : ill., Text
RightsPublic, Fribush, Howard M., Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved.

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