Intramolecular donor–acceptor interaction between aromatic amines and quinones

Carruthers, Robert J.; Dean, F. M.; Houghton, L. E.; Ledwith, A.

doi:10.1039/c19670001206

Cited by 3 publications

(2 citation statements)

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“…Im ' H-NMR-Spektrum von 6 Benzol474 nm) sowie die lineare Abhangigkeit der Extinktion von der Konzentration sprechen fiir eine intramolekulare CT-Wechselwirkung zwischen dem Chinon-und dem Anilin-Teil von 8. Damit kann 8 als Chinhydron aufgefaBt werden, das in seiner Struktur zwischen den intermolekularen Chinhydronen und den intramolekularen vom 2.2-Paracyclophan-Typus3') steht.…”

Section: -Methyl-3-(n-4'-hydroxyphenyl)-ammo-l4-naphthochinon (7)unclassified

Chinon‐Amin‐Reaktionen, 1. Mitt. Reaktionen zwischen 2‐Methyl‐1,4‐naphthochinon und 4‐Aminophenol

Kallmayer

1979

Archiv der Pharmazie

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2‐Methyl‐1,4‐naphthochinon (1) reagiert mit 4‐Aminophenol zu 2‐Methyl‐1,4‐naphthochinon‐4‐(N‐4′‐hydroxyphenyl)‐imin (6), 2‐Methyl‐3‐(4′‐hydroxyphenyl)amino‐1,4‐naphthochinon (7) und 2‐(N‐4′‐Hydroxyphenyl)‐aminomethyl‐1,4‐naphthochinon (8) (MS, 1H‐NMR, IR, UV/S). Tautomere der Reaktionsprodukte werden diskutiert. Die Farbe von 8 wird auf intramolekulare CT‐Wechselwirkung zwischen Chinon‐ und Anilinteil des Moleküls zurückgeführt.

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Section: -Methyl-3-(n-4'-hydroxyphenyl)-ammo-l4-naphthochinon (7)unclassified

Chinon‐Amin‐Reaktionen, 1. Mitt. Reaktionen zwischen 2‐Methyl‐1,4‐naphthochinon und 4‐Aminophenol

Kallmayer

1979

Archiv der Pharmazie

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“…In suitably designed structures reliable probes for the detection of these folded conformations are: (i) intranlolecular (de)shielding effects in n.m.r. spectra and (ii) intramolecular charge-transfer (CT) interaction between donor (D) and acceptor (A) groups which are positioned in the vicinity of each other as a result of the folding of the molecule (2,(7)(8)(9)(10)(11)(12)(13).…”

Section: Introductionmentioning

confidence: 99%

Folded Conformations. IV. Intramolecular Shielding and Intramolecular Charge-Transfer Interaction in Benzyl Phenyl Sulfones and Sulfoxides

Vanestst.R¹,

Engberts²

1973

Can. J. Chem.

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Proton magnetic resonance spectraof the title compounds (A-S02CHR-D) were measured and compared with the spectra of appropriate reference systems containing an alkyl substituent instead of one of the aromatic rings. The observed upfield shifts ofthe aromatic proton resonances in the title compounds suggest that there is a significant population of folded conformations, which possess a gauche orientation of the aromatic rings. This conclusion is supported by the observation of an intramolecular charge-transfer band in the U.V. spectra of the compounds containing an A ring of high electron affinity and a D ring of low ionization potential. Stabilization of the folded forms may be obtained through minimizing the n-a repulsive forces between the sulfonyl oxygen lone pairs and the a-electron system of the D ring. [Traduit par le journal]Can.

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Studies of inter‐ and intra‐molecular donor‐acceptor interactions ‐ X: Intramolecular Charge transfer interaction in substituted N‐aralkyl‐phthalimides and ‐1,8‐naphthalimides

Craenen

Verhoeven

Boer

1972

Recl. Trav. Chim. Pays‐Bas

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A (n = 1-5) are studied, in which D = an aromatic group with low ionization potential (e.g. an electron donor) and A is mainly the N-3,6dinitro-1,8-naphthalimide group. Especially for n = 1 and n = 3, interaction between D and A leads to the observation of discrete intramolecular C(harge) T(ransfer) transitions in the electronic .absorption spectra. For n = 1 this is explained by "homoconjugative" interaction, while for n = 3 the molecules probably adopt a folded conformation, a suggestion which is suppported by NMR data. For n = 2 close approach of D and A seems to be sterically excluded, while for n > 3 the interaction between D and A rapidly diminishes.For the compound with D = 9-anthryl and n = 3 steric interaction between the peri-hydrogens of the anthryl group and the trimethylene chain seems to inhibit the molecule from adopting a folded conformation. For the compounds with D = p-dimethylaminophenyl and n = 3 or 4 a double intramolecular CT transitien is observed; a tentative explanation for this phenomenon is given.

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Intramolecular donor–acceptor interaction between aromatic amines and quinones

Cited by 3 publications

References 0 publications

Chinon‐Amin‐Reaktionen, 1. Mitt. Reaktionen zwischen 2‐Methyl‐1,4‐naphthochinon und 4‐Aminophenol

Chinon‐Amin‐Reaktionen, 1. Mitt. Reaktionen zwischen 2‐Methyl‐1,4‐naphthochinon und 4‐Aminophenol

Folded Conformations. IV. Intramolecular Shielding and Intramolecular Charge-Transfer Interaction in Benzyl Phenyl Sulfones and Sulfoxides

Studies of inter‐ and intra‐molecular donor‐acceptor interactions ‐ X: Intramolecular Charge transfer interaction in substituted N‐aralkyl‐phthalimides and ‐1,8‐naphthalimides

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