TY - JOUR
T1 - Competition between OH⋯O and multiple halogen-dipole interactions on the formation of intramolecular three-centred hydrogen bond in 3-acyl coumarins
AU - Santos-Contreras, Rocío J.
AU - Martínez-Martínez, Francisco J.
AU - Mancilla-Margalli, N. Alejandra
AU - Peraza-Campos, Ana L.
AU - Morín-Sánchez, Luis M.
AU - García-Báez, Efrén V.
AU - Padilla-Martínez, Itzia I.
PY - 2009
Y1 - 2009
N2 - This paper describes the synthesis and structural study in solution, by NMR, and in the solid state, by X-ray analysis, of 6-substituted (H, NO 2, OCH3, Cl, Br) 2-oxo-2H-chromene-3-carboxylic acid (2-hydroxy-ethyl) amides. The results were supported by ab initio calculations at RHF-631G** level of theory. The crystal structures of compounds 6-Cl and 6-Br show deviations from the predicted theoretical conformation and also from that observed in solution, pointing to the influence exerted by intermolecular interactions on the molecular structure and on intramolecular three-centred hydrogen bond formation (O2⋯H12⋯O1). The significance of the plethora of non-covalent interactions [C H⋯A (A = O, X, π), CO⋯CO, CO⋯π, C X⋯OC (X = halogen), Br⋯Br and ππ stacking] is discussed.
AB - This paper describes the synthesis and structural study in solution, by NMR, and in the solid state, by X-ray analysis, of 6-substituted (H, NO 2, OCH3, Cl, Br) 2-oxo-2H-chromene-3-carboxylic acid (2-hydroxy-ethyl) amides. The results were supported by ab initio calculations at RHF-631G** level of theory. The crystal structures of compounds 6-Cl and 6-Br show deviations from the predicted theoretical conformation and also from that observed in solution, pointing to the influence exerted by intermolecular interactions on the molecular structure and on intramolecular three-centred hydrogen bond formation (O2⋯H12⋯O1). The significance of the plethora of non-covalent interactions [C H⋯A (A = O, X, π), CO⋯CO, CO⋯π, C X⋯OC (X = halogen), Br⋯Br and ππ stacking] is discussed.
UR - http://www.scopus.com/inward/record.url?scp=67650447388&partnerID=8YFLogxK
U2 - 10.1039/b818309k
DO - 10.1039/b818309k
M3 - Artículo
SN - 1466-8033
VL - 11
SP - 1451
EP - 1461
JO - CrystEngComm
JF - CrystEngComm
IS - 7
ER -