TY - JOUR
T1 - Switching from twisted to planar oxalamide molecular clefts through intramolecular three centered hydrogen bonding
AU - Padilla-Martínez, Itzia I.
AU - Martínez-Martínez, Francisco J.
AU - Guillén-Hernández, Cristian I.
AU - Chaparro-Huerta, María
AU - Cabrera-Pérez, Laura C.
AU - Gómez-Castro, Carlos Z.
AU - López-Romero, Beatriz A.
AU - García-Báez, Efrén V.
PY - 2005/8/23
Y1 - 2005/8/23
N2 - The design, synthesis and structural characterization of thirteen bis-oxalamide molecular clefts are reported. 1H NMR chemical shifts and -Δδ/ΔT coefficients of the NH protons were used to evaluate their mobilities and the role of hydrogen bonding interactions in stabilizing twisted or planar clefts in solution. Ab initio molecular orbital calculations at HF/6-31++G level of theory supported the experimental results. Finally the use of three-centered hydrogen bonding interactions to switch from twisted to planar molecular clefts was demonstrated.
AB - The design, synthesis and structural characterization of thirteen bis-oxalamide molecular clefts are reported. 1H NMR chemical shifts and -Δδ/ΔT coefficients of the NH protons were used to evaluate their mobilities and the role of hydrogen bonding interactions in stabilizing twisted or planar clefts in solution. Ab initio molecular orbital calculations at HF/6-31++G level of theory supported the experimental results. Finally the use of three-centered hydrogen bonding interactions to switch from twisted to planar molecular clefts was demonstrated.
KW - Oxalamide
KW - Oxamide
KW - Planar clefts
KW - Temperature dependence coefficient
KW - Three centered hydrogen bond
KW - Tweezer type clefts
UR - http://www.scopus.com/inward/record.url?scp=24044440969&partnerID=8YFLogxK
M3 - Artículo
SN - 1424-6376
VL - 2005
SP - 401
EP - 415
JO - Arkivoc
JF - Arkivoc
IS - 6
ER -