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Experimental and computational studies on a protonated 2-pyridinyl moiety and its switchable effect for the design of thermolytic devices.

By Jolanta Brzezinska, Jacek Kujawski, Agnieszka Witkowska, Kornelia Czaja, Marek K Bernard and Marcin K Chmielewski and Marcin K Chmielewski

Abstract

1D and 2D NMR investigations as well as computational studies, including static quantum-mechanics calculations, density function theory formalism, and classical molecular dynamics, were applied to determine the protonation sites in the thermolabile protecting group (TPG) containing a 2-pyridynyl moiety within its structure. This protecting group has three possible sites for protonation: an azomethine (pyridinic) atom (N1), 2-aminoethanol residue (N2), and 4-amino substituent (N4). Our investigations showed that the protonation mainly occurs on the N1 atom. Such protonation seems to be a major inhibitory factor in the thermal removal of 2-pyridynyl TPG by the "chemical switch" approach and decreases the aromaticity of the pyridine ring. We also discussed possible participation of N2 nitrogen in irreversible intramolecular cyclization under acidic conditions

Topics: Medicine, R, Science, Q
Publisher: Public Library of Science (PLoS)
DOI identifier: 10.1371/journal.pone.0203604
OAI identifier: oai:doaj.org/article:04953978a72448b0ac7e257451b405b1
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