TY - JOUR
T1 - Supramolecular assembly of 2-aminobenzothiazole and N-[(2-oxo-2H-1- benzopyran-3-yl)carboxyl]phenethylamide donor-acceptor complex. A comparative study
AU - García-Báez, Efrén V.
AU - Martínez-Martínez, Francisco J.
AU - Höpfl, Herbert
AU - Padilla-Martínez, Itzia I.
PY - 2003
Y1 - 2003
N2 - In this paper the synthesis and solid state characterization of the donor-acceptor (D-A) complex between 2-aminobenzothiazole (ABT) and N-[(2-oxo-2H-1-benzopyran-3-yl)carboxyl]phenethylamide is reported. A comparison is performed with other aminobenzothiazole-coumarin complexes reported earlier and the results are analyzed in the context of crystal engineering. A common feature of these structures is the presence of a building block formed by pair-wise self complementary NH⋯N interactions between two molecules of ABT, defining an R22 (8) motif. The complete three-dimensional supramolecular arrangement is achieved by both strong (NH⋯O) and weak (CH⋯X, X = O, aryl) H-bonding interactions which define an A⋯D⋯D'⋯A' hydrogen bonded tetrameric unit, which packs through π-stacking interactions. The resulting donor-acceptor assemblies present two patterns of alternated stacking: D-A and D-A-A'-D'. Finally, the factors ruling the supramolecular isomerism exhibited by these complexes and the nature of the interactions are discussed and supported by ab initio theoretical calculations.
AB - In this paper the synthesis and solid state characterization of the donor-acceptor (D-A) complex between 2-aminobenzothiazole (ABT) and N-[(2-oxo-2H-1-benzopyran-3-yl)carboxyl]phenethylamide is reported. A comparison is performed with other aminobenzothiazole-coumarin complexes reported earlier and the results are analyzed in the context of crystal engineering. A common feature of these structures is the presence of a building block formed by pair-wise self complementary NH⋯N interactions between two molecules of ABT, defining an R22 (8) motif. The complete three-dimensional supramolecular arrangement is achieved by both strong (NH⋯O) and weak (CH⋯X, X = O, aryl) H-bonding interactions which define an A⋯D⋯D'⋯A' hydrogen bonded tetrameric unit, which packs through π-stacking interactions. The resulting donor-acceptor assemblies present two patterns of alternated stacking: D-A and D-A-A'-D'. Finally, the factors ruling the supramolecular isomerism exhibited by these complexes and the nature of the interactions are discussed and supported by ab initio theoretical calculations.
KW - 2-aminobenzothiazole
KW - 3-carboxycoumarins
KW - Donor-acceptor complexes
KW - Hydrogen bonding
KW - π-stacking
UR - http://www.scopus.com/inward/record.url?scp=3242725890&partnerID=8YFLogxK
M3 - Artículo
SN - 1424-6376
VL - 2003
SP - 100
EP - 111
JO - Arkivoc
JF - Arkivoc
IS - 11
ER -