Ab initio GB study of the acid-catalyzed cis–trans isomerization of methyl yellow and methyl orange in aqueous solution

Azuki, Masayuki; Morihashi, Kenji; Watanabe, Takeharu; Takahashi, Ohgi; Kikuchi, Osamu

doi:10.1016/s0166-1280(00)00855-1

Cited by 28 publications

(35 citation statements)

References 28 publications

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“…The cis-trans isomerization occurs by photoirradiation with UV light or by heating. It is generally accepted that their trans forms are more stable than their cis forms [7,8]. In addition, molecular azo dyes are still one of the active research topics in the area of molecular engineering of optoelectronic materials [9] and photoswitchable molecules [10] due to their enhanced chemical stability and photostability.…”

Section: Introductionmentioning

confidence: 99%

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

et al. 2009

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The molecular and crystal structure of (E)-2-Acetyl-4-(2-bromophenyldiazenyl)phenol (1) and (E)-2-Methyl-4-(o-tolyldiazenyl)phenol (2) were characterized and determined by single crystal X-ray diffraction method besides spectroscopic means. The periodic organization of 1 is stabilized by C-HÁÁÁO type weak H-bond and BrÁÁÁO type weak halogen bonding and thus, a two dimensional puckered network is established almost parallel to (101) the plane. Molecules of 2 are linked into C(7) chains generated by translation along the [1 0 1] direction with the aid of O-HÁÁÁN type H-bonds, and these chains are strengthened by C-HÁÁÁp interactions involving o-tolylphenol ring. Quantum chemical studies at B3LYP/6-311 ??G(d,p) level reveal that potential barrier of the compounds around Ar-N torsions is of double minimum character unless it is defected by the presence of o-substituent groups in the vicinity of the azo bridge. The results from crystallographic and quantum chemical studies suggest that azo benzene compounds may adapt non-planar geometry apart from the most stable planar conformation, which is located on the secondary minima of double potential barrier regarding rotational motion around Ar-N bonds.

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Section: Introductionmentioning

confidence: 99%

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

et al. 2009

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“…The trans-to-cis isomerization occurs by photoirradiation with UV light and cis-to-trans isomerization proceeds with blue-light irradiation or heating. It is generally accepted that their trans forms are thermodynamically more stable than their cis forms [7,8]. On the other hand, azo benzene compounds exhibit unusual molecular motion referred to as pedal motion in solid state leading to orientational disorder in azo bridge at either one of the lattice sites [9] or both crystal lattice sites [10].…”

Section: Introductionmentioning

confidence: 99%

“…(7) and C(8) polymeric chains along [1 0 0] direction. H atoms not involved in the motifs have been omitted for the sake of clarity…”

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confidence: 99%

Crystallographic and conformational analysis of (E)-2-isopropyl-4-(p-tolyldiazenyl)phenol

et al. 2008

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The molecular and crystal structures of the title compound, C 16 H 18 N 2 O, were characterized and determined by single crystal X-ray diffraction method in addition to spectroscopic means such as IR, UV-VIS and 1 H NMR. The compound crystallizes in orthorhombic space group P bca, with a = 9.3350(5) Å , b = 23.4878(13) Å , c = 26.5871 (12) Å , Z = 16, D calc. = 1.1591(1) g/cm 3 , l (MoK a ) = 0.073 mm -1 . Monomers of the compound in the crystal structure are linked into C(7) and C(8) chains generated by translation along the [1 0 0] direction with the aid of O-HÁÁÁN type H-bonds which serve to the stabilization of periodic organization of the molecules beside major and minor component in the disordered azo fragment. In order to describe conformational flexibility and the crystal packing effects on the molecular conformation, potential barriers regarding the rotation along both Ar-N bonds were calculated by varying the related torsional degrees of freedom in every 10°ranging from -180°to +180°via quantum chemical calculations at DFT/B3LYP level.

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“…The trans-to-cis isomerization occurs by photoirradiation with UV light and cis-totrans isomerization proceeds with blue-light irradiation or by heating. It is generally accepted that their trans forms are thermodynamically more stable than their cis forms [8,9].…”

Section: Introductionmentioning

confidence: 99%

Conformational analysis and crystal structure of (E)-3-methyl-4-(p-tolyldiazenyl)phenol

et al. 2006

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The single crystal X-ray diffraction analysis of the title compound, C 14 H 14 N 2 O, reveals that an interesting intermolecular or extended structure (hydrogenbonded polymeric zigzag chains) is formed by linking its monomer units with O-H · · · N type intermolecular hydrogen bonds. The compound crystallizes in the monoclinic space group P2 1 /n with a = 5.8151(5) Å, b = 18.106(1) Å, c = 11.515(1) Å and β = 96.891 (7) • . In order to understand better its structural aspects in solid state, quantum chemical (PM3) calculations were performed on a part of the extended structure of the title compound containing ten monomers. To determine in vacuo conformational flexibility of the compound, molecular energy profile of the title compound was obtained with respect to a selected torsional degree of freedom and the pedal angle varied from − 180 • to + 180 • in every 10 • . The results from the computational study suggest that hydrogen-bonding properties in the crystal lattice is fundamental in determining the crystallographically observed conformation of the title compound.

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Ab initio GB study of the acid-catalyzed cis–trans isomerization of methyl yellow and methyl orange in aqueous solution

Cited by 28 publications

References 28 publications

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

Crystallographic and conformational analysis of (E)-2-isopropyl-4-(p-tolyldiazenyl)phenol

Conformational analysis and crystal structure of (E)-3-methyl-4-(p-tolyldiazenyl)phenol

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