TY - JOUR
T1 - Further insight into three center hydrogen bonding. Participation in tautomeric equilibria of heterocyclic amides
AU - Padilla-Martínez, Itzia I.
AU - Martínez-Martínez, Francisco J.
AU - García-Báez, Efrén V.
AU - Torres-Valencia, J. Martín
AU - Rojas-Lima, Susana
AU - Höpfl, Herbert
PY - 2001
Y1 - 2001
N2 - In this work the synthesis and characterization in solution and solid state of three heterocyclic oxamides and four amides capable of forming three center hydrogen bond (THB) interactions is described. The formation of THBs in solution was established and studied by multinuclear and VT 1H magnetic resonance, by which the Δδ/ΔT values could be directly related with proton mobility. The molecular structure of two oxamides in the solid state was determined by X-ray diffraction experiments. The results showed that amides with S(n)S(5)S(6) (n = 5, 6 for -OMe and -NO2 respectively) motifs were less prone to establish tautomeric equilibria in solution than those with the simpler S(n)S(5) motif.
AB - In this work the synthesis and characterization in solution and solid state of three heterocyclic oxamides and four amides capable of forming three center hydrogen bond (THB) interactions is described. The formation of THBs in solution was established and studied by multinuclear and VT 1H magnetic resonance, by which the Δδ/ΔT values could be directly related with proton mobility. The molecular structure of two oxamides in the solid state was determined by X-ray diffraction experiments. The results showed that amides with S(n)S(5)S(6) (n = 5, 6 for -OMe and -NO2 respectively) motifs were less prone to establish tautomeric equilibria in solution than those with the simpler S(n)S(5) motif.
UR - http://www.scopus.com/inward/record.url?scp=0034741435&partnerID=8YFLogxK
U2 - 10.1039/b103063a
DO - 10.1039/b103063a
M3 - Artículo
SN - 1470-1820
VL - 9
SP - 1817
EP - 1823
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
ER -