2018
DOI: 10.1107/s2056989018003687
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Crystal structures and antioxidant capacity of (E)-5-benzyloxy-2-{[(4-chlorophenyl)imino]methyl}phenol and (E)-5-benzyloxy-2-({[2-(1H-indol-3-yl)ethyl]iminiumyl}methyl)phenolate

Abstract: The title Schiff base compounds, (I) and (II), were synthesized via the condensation reaction of 2-amino-4-chloro­phenol for (I), and 2-(2,3-di­hydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benz­yloxy-2-hy­droxy­benzaldehyde. In both compounds, there is an intra­molecular hydrogen bond forming an S(6) ring motif; an O—H⋯O hydrogen bond in (I), but a charge-assisted N+—H⋯O− hydrogen bond in (II).

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Cited by 5 publications
(3 citation statements)
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“…4 , Supplementary Information). All the results realized herein are similar to those found in the previous studies [33] , [34] , [35] .…”
Section: Resultssupporting
confidence: 92%
“…4 , Supplementary Information). All the results realized herein are similar to those found in the previous studies [33] , [34] , [35] .…”
Section: Resultssupporting
confidence: 92%
“…Therefore, we decided to analyze the interactions between the NH site and six-membered rings in detail. The distances from the hydrogen atom of the NH site, which was placed according to the residual peaks of the electron density (N–H distance of 0.88(5) Å (not restrained)), to the six-membered rings (2.61(5) and 2.83(5) Å; Figure a) and the angles formed by the N–H bond and the line perpendicular to the six-membered rings from the hydrogen atom (134(3)° and 108(3)°; Figure a) are within the range previously reported for several organic crystals that have been reported to form weak N–H···π interactions (2.35(2)–3.01(5) Å, average 2.66(22); 107(3)–166.32(18)°, average 143(18)°). We also performed a Hirshfeld surface analysis for the surface of the NH site using CrystalExplorer . Blue-colored highlights pointing toward the six-membered rings were observed from the NH site (Figure b, left), suggesting the presence of contacts longer than the van der Waals contact .…”
Section: Resultssupporting
confidence: 80%
“…Many ylide compounds show widespread applications in organic chemistry [5][6][7][8]. In this paper, we report the synthesis of the side-product of the reaction of (2- (O2-C19) and 1.250(5) Å (O3-C19), respectively.…”
Section: Commentmentioning
confidence: 99%