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• W1994196619 endingPage "6801" @default.
• W1994196619 startingPage "6790" @default.
• W1994196619 abstract "The results are presented of a theoretical study of the nitrosation chemistry of pyrroline 1 (X = CH2), imidazoline 2 (X = NH), and 2-oxazoline 3 (X = O). Imines 1−3 are converted to the α-hydroxy-N-nitrosamines 7−9 via the N-nitrosoiminium ions 4−6. The NN-cis isomers of 7−9 may undergo retro-ene reactions to the δ-oxoalkyl diazotic acids 10−12. With the opportunity for microsolvation, C−X cleavage becomes possible for 8 and 9 and leads to the formation of N-(2-aminoethyl)- and N-(2-hydroxyethyl)-N-nitrosoformamides 15 and 16, respectively. The NN-isomerization barriers are comparable to the barriers for the ring-opening reactions, and the consideration of two Curtin−Hammett scenarios is required: CH-I for the NN-trans-rotamers of 7−9 to undergo C−X cleavage or NN-isomerization and CH-II for the NN-cis-rotamers to undergo C−X cleavage, C−N cleavage, or NN-isomerization. We determined all stereoisomers of the substrates, the products, and of all transition states structures for the retro-ene reactions of 7−9, the C−X cleavages of microsolvated 8 and 9, and the NN-isomerizations of 8 and 9. The potential energy surfaces were explored at the B3LYP/6-31G** level, and the results are discussed with emphasis on the comparison of the kinetics and thermodynamics of C−N versus C−X cleavage. The study shows all decompositions to be very fast with activation barriers below 21 kcal·mol-1, and the comparitive analysis predicts that the chemical toxicologies of 1 and 3 should be similar and remarkably different from that of 2." @default.
• W1994196619 created "2016-06-24" @default.
• W1994196619 creator A5033148406 @default.
• W1994196619 creator A5051637510 @default.
• W1994196619 creator A5053438967 @default.
• W1994196619 date "2005-07-23" @default.
• W1994196619 modified "2023-10-03" @default.
• W1994196619 title "Nitrosation Chemistry of Pyrroline, 2-Imidazoline, and 2-Oxazoline: Theoretical Curtin−Hammett Analysis of Retro-Ene and Solvent-Assisted C−X Cleavage Reactions of α-Hydroxy-<i>N</i>-Nitrosamines" @default.
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• W1994196619 doi "https://doi.org/10.1021/jo050856s" @default.
• W1994196619 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16095298" @default.
• W1994196619 hasPublicationYear "2005" @default.
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