TY - JOUR
T1 - The zwitterion of 4-nitro-2-{(E)-[2-(piperidin-1-yl)eth-yl]imino-meth-yl}- phenol
AU - Santos-Contreras, Rocio J.
AU - Ramos-Organillo, Angel
AU - García-Báez, Efrén V.
AU - Padilla-Martínez, Itzia I.
AU - Martínez-Martínez, Francisco J.
PY - 2009
Y1 - 2009
N2 - The title Schiff base compound, 4-nitro-1-oxo-2-{(E)-[2-(piperidin-1-yl) eth-yl]iminiometh-yl}cyclo-hexa-dienide, C14H19N3O3, exists as a zwitterion, with the H atom of the phenol group being transferred to the imine N atom. The C=O, CAr - CAr and C - N bond lengths are in agreement with the oxocyclo-hexa-dienide-iminium zwitterionic form. The iminium H atom is engaged in a strong intra-molecular hydrogen bond with the O atom of the keto group (N+ - H⋯O) to form an S(6) motif. Soft C - H⋯O inter-actions in the ac plane lead to the development of hydrogen-bonded tapes, which are π-stacked through the oxocyclo-hexa-dienide ring and iminium group. The significance of this study is in providing crystallographic evidence, supported by NMR and IR data, of the predominance of the oxocyclo-hexa-dienide- iminium zwitterion form over the noncharged canonical form in the title Schiff base.
AB - The title Schiff base compound, 4-nitro-1-oxo-2-{(E)-[2-(piperidin-1-yl) eth-yl]iminiometh-yl}cyclo-hexa-dienide, C14H19N3O3, exists as a zwitterion, with the H atom of the phenol group being transferred to the imine N atom. The C=O, CAr - CAr and C - N bond lengths are in agreement with the oxocyclo-hexa-dienide-iminium zwitterionic form. The iminium H atom is engaged in a strong intra-molecular hydrogen bond with the O atom of the keto group (N+ - H⋯O) to form an S(6) motif. Soft C - H⋯O inter-actions in the ac plane lead to the development of hydrogen-bonded tapes, which are π-stacked through the oxocyclo-hexa-dienide ring and iminium group. The significance of this study is in providing crystallographic evidence, supported by NMR and IR data, of the predominance of the oxocyclo-hexa-dienide- iminium zwitterion form over the noncharged canonical form in the title Schiff base.
UR - http://www.scopus.com/inward/record.url?scp=58149519334&partnerID=8YFLogxK
U2 - 10.1107/S0108270108040407
DO - 10.1107/S0108270108040407
M3 - Artículo
SN - 0108-2701
VL - 65
SP - o8-o10
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
IS - 1
ER -