Une Serie de N-(2,3-Dihydroxybenzilidene)amines: Manifestation d'Equilibres Tautomères

Mansilla-Koblavi, F.; Tenon, J. A.; Toure, S.; Ebby, N.; Lapasset, J.; Carles, Micheline

doi:10.1107/s0108270194002945

Cited by 21 publications

(12 citation statements)

References 15 publications

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“…In the crystalline lattice these molecules are present mainly as dimers but trimers or even polymeric associations are also formed. 3,4 These compounds are exclusively thermochromic because their compact structure inhibits the intramolecular isomerization required to exhibit photochromic properties. In this work our main concern is to evaluate the importance of proton transfers occurring in six thermochromic Scheme 1 Tautomeric equilibrium in compounds 1-6.…”

Section: Introductionmentioning

confidence: 99%

“…So far, the dynamics of this problem had only been studied by IR. 3,6 Two series of compounds were synthesized (Scheme 1): one (1-3) with aliphatic R groups (R = Me, iPr, tBu), the other formed of phenyl derivatives bearing different substituents (4)(5)(6). The substituents were chosen for their well-known electron-donating or electronwithdrawing properties.…”

Section: Introductionmentioning

confidence: 99%

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Tautomerism in Schiff bases derived from 3-hydroxysalicylaldehyde. Combined X-ray diffraction, solution and solid state NMR study

Pizzala

Carles

Stone

et al. 2000

J. Chem. Soc., Perkin Trans. 2

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tautomerism in Schiff bases derived from 3-hydroxysalicylaldehyde. Combined X-ray diffraction, solution and solid state NMR study

Pizzala

Carles

Stone

et al. 2000

J. Chem. Soc., Perkin Trans. 2

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“…A significant example is given by the structure of 2-hydroxy-5-(isopropylaminomethylene)-2,4-cyclohexadien-1-one (ZAMMIJ; Fig. (9a)) [57]. The importance of this supplementary interaction in inducing proton transfer is stressed by the structure of 2,3-bis(salicylideneamino)-1,4-butanediol (ROBPAZ01; Fig.…”

Section: -(1-alkyiminomethyl)phenols (Class Ii)mentioning

confidence: 98%

Section: I(b) I(a)mentioning

confidence: 99%

“…3-(2-chlorophenyliminomethyl)-1,2-benzenediol (ZAMMEF) [57], 3-(phenyliminomethyl)1, 2-benzenediol ((ZAMLUU; Fig. (5a)) [57] and N-(2,3-dihydroxybenzylidene)(4-(N',N'-dimethylamino)phenyl) amine (LOFSOO) [58]. In some cases the intermolecular Hbond interaction on the OH phenolic group does not produce any transition from SW to DW profile but only a moderate shortening of the O-H…N bond with N…O distances down to 2.55 Å, as exemplified by the structure of N-(3-hydroxyphenyl)-5-methoxysalicylaldimine ((BALHUS01; Fig.…”

Section: I(b) I(a)mentioning

confidence: 99%

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Crystal Chemistry and Prototropic Tautomerism in 2-(1-Iminoalkyl)- phenols (or naphthols) and 2-Diazenyl-phenols (or naphthols)

Bertolasi¹,

Gilli

2009

COC

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This review reports a systematic investigation, carried out on the Cambridge Crystallographic Database (CSD), on the structural features of iminoalkyl-phenols (or naphthols) as well as azo-phenols (or naphthols). All these compounds form N-H…O/O-H…N intramolecular hydrogen bonds assisted by resonance (RAHB) in tautomeric equilibrium which can be finely tuned by the substituents. Accordingly, they can present reversible proton transfer leading to interesting properties such as thermochromism and photochromism. The phenol derivatives 2-(1-aryliminoalkyl)phenols and 2-arylazophenols display the predominance of the O-H…N form. Furthermore, they display the following features: i) strongly electron-donating substituents in p-position on the N-phenyl group shorten the N…O contact distance but not enough to produce the O-H…N to O-H…N/N-H…O transition; ii) such a transition can be however induced by strongly electron-withdrawing substituents at the phenol ring which increase the phenol acidity; iii) very similar effects are determined by intermolecular hydrogen-bonded O-H…O contacts with the phenolic oxygen which, stabilizing the N-H…O bond produce the O-H…N to O-H…N/N-H…O transition and, sometimes, the complete proton transfer to the pure N-H…O form. The naphthol derivatives (1-(1-aryliminoalkyl-2-naphthols and 1-arylazo-2-naphthols) display the most interesting situation of two roughly isoenergetic O-H…N/N-H…O tautomers which can be tuned by modifying the Nsubstituent, the effects of substitution at the N-phenyl moiety being by far the most extensively studied. The structures of variously aryl-substituted 1-(1-aryliminoalkyl)-2-naphthols, though collected only at room temperature, indicate that almost all of them are tautomeric equilibria, even if full information on proton populations and dynamic or static nature of the proton disorder are not available. Conversely, the structures of a series of aryl-substituted 1-arylazo-2-naphthols have been recently determined at variable temperature showing that strongly electron-attracting substituents stabilize the pure N-H…O form, while substituents with increasing electron-donating properties transform the system into a dynamic, or static, N-H…O O-H…N tautomeric equilibrium in the solid with an ever increasing population of the O-H…N azoenol tautomer.

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Tautomeric Equilibria and Rearrangements Involving Phenols

Koblik¹

2009

Patai's Chemistry of Functional Groups

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Introduction Tautomerism in Phenols Rearrangements of Phenols Rearrangements of O ‐Substituted Phenol Derivatives Rearrangements of Functionalized Arenes Rearrangements of Non‐Aromatic Carbocycles Rearrangements of Heterocyclic Compounds

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Une Serie de N-(2,3-Dihydroxybenzilidene)amines: Manifestation d'Equilibres Tautomères

Abstract: The crystal structures of five N-(2,3-dihydroxybenzylidene)amine derivatives, C7H6NO2--R [R = phenyl (1), p-methylphenyl (2), o-chlorophenyl (3), isopropyl (4) and cyclopropyl (5)] are presented and discussed.

Cited by 21 publications

References 15 publications

Tautomerism in Schiff bases derived from 3-hydroxysalicylaldehyde. Combined X-ray diffraction, solution and solid state NMR study

Tautomerism in Schiff bases derived from 3-hydroxysalicylaldehyde. Combined X-ray diffraction, solution and solid state NMR study

Crystal Chemistry and Prototropic Tautomerism in 2-(1-Iminoalkyl)- phenols (or naphthols) and 2-Diazenyl-phenols (or naphthols)

Tautomeric Equilibria and Rearrangements Involving Phenols

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