N-(5-Hydroxysalicylidène)-2,4,6-triméthylaniline

Tenon, J. A.; Carles, Micheline; Aycard, Jean‐Pierre

doi:10.1107/s0108270195007967

Cited by 4 publications

(2 citation statements)

References 5 publications

(5 reference statements)

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“…All structures elucidated by single-crystal diffraction exhibit a strong intramolecular hydrogen bond leading to a six-membered ring whose geometric characteristics are collected in Table S2 . Table 1 compares some bonding distances obtained by X-ray analyses of 24 and 40 – 41 , with the average values of similar structures described as phenoliminic tautomers [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ] and ketoamines [ 32 , 33 , 34 ] in the Cambridge Structural Database ( Figure 13 ). The analysis of bond distances in compounds 40 and 42 indicates that the values of d C2-C3 and d C4-O5 are in full agreement with an enamine structure.…”

Section: Resultsmentioning

confidence: 99%

Schiff Bases and Stereocontrolled Formation of Fused 1,3-Oxazolidines from 1-Amino-2-Indanol: A Systematic Study on Structure and Mechanism

et al. 2023

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This paper thoroughly explores the formation of Schiff bases derived from salicylaldehydes and a conformationally restricted amino alcohol (1-amino-2-indanol), as well as the generation of 1,3-oxazolidines, a key heterocyclic core present in numerous bioactive compounds. We provide enough evidences, both experimental-including crystallographic analyses and DFT-based calculations on imine/enamine tautomerism in the solid state and solution. In the course of imine formation, a pentacyclic oxazolidine–oxazine structure could be isolated with complete stereocontrol, whose configuration has been determined by merging theory and experiment. Mechanistic studies reveal that, although oxazolidines can be obtained under kinetic conditions, the prevalence of imines obeys to thermodynamic control as they are the most stable structures. The stereochemical outcome of imine cyclization under acylating conditions leads to formation of 2,4-trans-oxazolidines.

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Section: Resultsmentioning

confidence: 99%

Schiff Bases and Stereocontrolled Formation of Fused 1,3-Oxazolidines from 1-Amino-2-Indanol: A Systematic Study on Structure and Mechanism

et al. 2023

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“…For 4-[(2-hydroxy-5-methoxybenzylidene)amino]benzonitrile (XIGNEI; Chiang et al, 2013), a complex with zinc is reported. In N-(5-hydroxysalicylidene)-2,4,6-trimethylaniline (ZIKNOW; Tenon et al, 1995), the angle between the planes of the benzene rings is 74.5 (1) and chlorine is absent.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Faizi

Çınar

Aydin

et al. 2020

Acta Crystallogr E Cryst Commun

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The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, and crystallizes in the monoclinic space group P21/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intramolecular O—H...N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H...H (43.8%) and C...H/H...C (26.7%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is provided.

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Novel Polyfunctional Tautomeric Systems Containing Salicylideneamino and Proton Sponge Moieties

et al. 2006

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The first salicylidenearylamines containing a proton sponge residue with 5′‐bromo (6), 5′‐nitro (7), and 3′,5′‐dinitro (8) substituents have been synthesized. X‐ray diffraction and 1H, 13C, and 15N NMR and infrared spectra revealed that 6 and 7 contain very strong OHN bridges typical of o‐hydroxy Schiff bases. Additional π‐electron coupling with the dimethylaminonaphthyl ring is manifested both in geometrical and infrared parameters. In the case of 7, proton transfer to the imine nitrogen atom occurs in the solid state, accompanied by a remarkable shortening of the OHN bridge (2.553 Å). In dinitro derivative 8, the OH proton jumps to the dimethylamino groups, giving a new tautomeric form with the formation of a homoconjugated [NHN]+ cation. Protonation of 6 and 7, affecting the (dimethylamino)naphthyl moiety, disrupts the π‐coupling and makes these molecules, unlike common aromatic Schiff bases, highly sensitive to hydrolysis, while 8, being already self‐protonated, equilibrates in wet DMSO with the corresponding salicylaldehyde and arylamine in a ca. 1:1 ratio at room temperature.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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N-(5-Hydroxysalicylidène)-2,4,6-triméthylaniline

Cited by 4 publications

References 5 publications

Schiff Bases and Stereocontrolled Formation of Fused 1,3-Oxazolidines from 1-Amino-2-Indanol: A Systematic Study on Structure and Mechanism

Schiff Bases and Stereocontrolled Formation of Fused 1,3-Oxazolidines from 1-Amino-2-Indanol: A Systematic Study on Structure and Mechanism

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Novel Polyfunctional Tautomeric Systems Containing Salicylideneamino and Proton Sponge Moieties

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