Structures of 1H-indole-3-ethylene-3'-methoxysalicylaldimine (3'-Meo-salTPA) and 3-[3'-azapentyl-3'-en-4'-(2''-hydroxyphenyl)]indole (OHAPH-TPA)

Zarza, P. Martin; Gill, Peter M. W.; Gonzalez, Myriam.; Reyes, María-Belen; Arrieta, Jm.; Nastopoulos, Vassilios; Germain, Gabriel; Debaerdemaeker, T.

doi:10.1107/s0108270187011739

Cited by 9 publications

(2 citation statements)

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“…Over the past decades, many ylide compounds have been received considerable attention, because they display widespread applications in organic chemistry [5][6][7][8]. Our goal was to synthesize a new Schiff base ligand and its manganese(II) complex.…”

Section: Commentmentioning

confidence: 99%

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

Tai

Zhou

Liu

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Commentmentioning

confidence: 99%

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

Tai

Zhou

Liu

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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“…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%

The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C₁₉H₁₈N₂O₃

Wang

Tai

2020

Zeitschrift Für Kristallographie - New Crystal Structures

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Neutral and Ionic Hydrogen Bonding in Schiff Bases

Dominiak

Grech

Barr

et al. 2003

Chemistry A European J

106

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Low-temperature, high-resolution X-ray studies of charge distributions in the three Schiff bases, the dianil of 2-hydroxy-5-methylisophthaldehyde, 3,5-dinitro-N-salicylidenoethylamine and 3-nitro-N-salicylidenocyclohexylamine, have been carried out. These structures exhibit interesting weak interactions, including two extreme cases of intramolecular hydrogen bonds that are ionic N(+)-H...O- and neutral O-H...N in nature. These two types of hydrogen bond reflect differences in geometrical parameters and electron density distribution. At the level of geometry, the neutral O-H...N hydrogen bond is accompanied by an increase in the length of the C(1)-O(1) bond, opening of the ipso-C(1) angle, elongation of the aromatic C-C bonds, shortening of the C(7)-N(2) bond and increased length of the C(1)-C(7) bond, relative to the ionic hydrogen bond type. According to the geometrical and critical point parameters, the neutral O-H...N hydrogen bond seems to be stronger than the ionic ones. There are also differences between charge density parameters of the aromatic rings consistent with the neutral hydrogen bond being stronger than the ionic ones, with a concomitant reduction in the aromaticity of the ring. Compounds with the ionic hydrogen bonds show a larger double-bond character in the C-O bond than appears in the compound containing a neutral hydrogen bond; this suggests that the electronic structure of the former pair of compounds includes a contribution from a zwitterionic canonical form. Furthermore, in the case of ionic hydrogen bonds, the corresponding interaction lines appear to be curved in the vicinity of the hydrogen atoms. In the 3-nitro-N-salicylidenocyclohexylamine crystal there exists, in addition to the intramolecular hydrogen bond, a pair of intermolecular O...H interactions in a centrosymmetric dimer unit.

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Structures of 1H-indole-3-ethylene-3'-methoxysalicylaldimine (3'-Meo-salTPA) and 3-[3'-azapentyl-3'-en-4'-(2''-hydroxyphenyl)]indole (OHAPH-TPA)

Cited by 9 publications

References 5 publications

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C₁₉H₁₈N₂O₃

Neutral and Ionic Hydrogen Bonding in Schiff Bases

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Structures of 1H-indole-3-ethylene-3'-methoxysalicylaldimine (3'-Meo-salTPA) and 3-[3'-azapentyl-3'-en-4'-(2''-hydroxyphenyl)]indole (OHAPH-TPA)

Cited by 9 publications

References 5 publications

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C17H15N2BrO

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C17H15N2BrO

The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C19H18N2O3

Neutral and Ionic Hydrogen Bonding in Schiff Bases

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The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C₁₇H₁₅N₂BrO

The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C₁₉H₁₈N₂O₃