The crystal and molecular structures of 2-hydroxy-1-naphthalenecarboxaldehyde and 3-hydroxy-2-naphthalenecarboxaldehyde

Fernández-G, Juan M.; Espinosa‐Pérez, Georgina

doi:10.1007/bf01833672

Cited by 4 publications

(2 citation statements)

References 10 publications

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“…For 4 as well, we assumed the formation of a similar intramolecular hydrogen bond, based on the substantial planarity of the OC−C−C−O moiety (the dihedral angle of OC−C−C is 2.92°) and the proximity of two oxygen atoms (O---O distance is 2.71 Å). These geometrical parameters are similar to those observed for their analogous compounds that have intramolecular hydrogen bond . IR spectra of 3 and 4 gave significantly broadened peaks at 3432 and 3302 cm −1 , respectively, which are attributable to the stretch vibration of intramolecularly hydrogen-bonded hydroxy groups.…”

Section: Resultssupporting

confidence: 76%

Experimental and Theoretical Studies on Constitutional Isomers of 2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted Hydrogen Bonding on the Electronic Absorption Spectra

et al. 2008

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We prepared and characterized a series of mono- and dicarbaldehydes of 2,6-dihydroxynaphthalene that bear potential resonance-assisted hydrogen bonding (RAHB) unit(s). X-ray crystal structures of selected compounds revealed that each salicylaldehyde moiety forms an intramolecular hydrogen bond and that the introduction of formyl groups into either the alpha- or beta-position causes a considerable difference in geometry, which was interpretative from a conventional scheme of resonance hybrids including ionic state. Analyses on NMR chemical shifts suggested that the compounds in solution are present as an equilibrium mixture between closed and open forms with respect to RAHB units. Ab initio calculations indicated that the formation of an intramolecular hydrogen bond strikingly influences the aromaticity of the individual local six-membered ring of naphthalene. The trend of the change in aromaticity was analyzed in connection with the extra stabilization energy of RAHB. In the UV-vis spectra, the beta-formyl derivatives specifically showed a substantial red shift compared to alpha-formyl derivatives. The absorption features were successfully reproduced by TD-DFT calculation, and those data were consistently explained from the effects of RAHB on electronic state of the naphthalene's pi-system. Finally, we pointed out a similarity in the electronic state between RAHB-bearing molecules and cata-condensed aromatic hydrocarbons.

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Section: Resultssupporting

confidence: 76%

Experimental and Theoretical Studies on Constitutional Isomers of 2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted Hydrogen Bonding on the Electronic Absorption Spectra

et al. 2008

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“…172 Apparently, this is attributed to destabilisation of the Z conformer due to Coulombic repulsion between the oxygen carbon atom and the oxygen atoms of the substituent in position 3. Evidently, one CHO group in naphthalene-2,3-dicarbaldehyde (167) occurs in the E conformation, whereas another CHO group exists in the Z form for the same reason. 173…”

Section: Results Of X-ray Diffraction Studiesmentioning

confidence: 99%

Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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Data on methods for the preparation of naphthalde-Data on methods for the preparation of naphthaldehydes, their physicochemical properties, structural characteristics hydes, their physicochemical properties, structural characteristics and reactivities are generalised. Particular attention is given to and reactivities are generalised. Particular attention is given to procedures for formylation of naphthalenes and procedures for formylation of naphthalenes and peri peri-interactions -interactions involving the aldehyde group in the involving the aldehyde group in the a a-position. The bibliography -position. The bibliography includes 201 references includes 201 references. .

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Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate

Zhang

2005

J Chem Crystallogr

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The crystal and molecular structures of 2-hydroxy-1-naphthalenecarboxaldehyde and 3-hydroxy-2-naphthalenecarboxaldehyde

Abstract: The crystal and molecular structures of 2-Hydroxy-l-naphthalenecarboxaldehyde (I) and 3-Hydroxy-2-naphthalenecarboxaldehyde (II) were determined. Compound (1)

Cited by 4 publications

References 10 publications

Experimental and Theoretical Studies on Constitutional Isomers of 2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted Hydrogen Bonding on the Electronic Absorption Spectra

Experimental and Theoretical Studies on Constitutional Isomers of 2,6-Dihydroxynaphthalene Carbaldehydes. Effects of Resonance-Assisted Hydrogen Bonding on the Electronic Absorption Spectra

Naphthaldehydes

Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate

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