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

Karabıyık, Hasan; Ískeleli, Nazan Ocak; Albayrak, Çiğdem; Ağar, Erbil

doi:10.1007/s11224-006-9130-1

Cited by 10 publications

(10 citation statements)

References 26 publications

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“…Some selected geometrical parameters experimentally obtained and their calculated values are listed in Table 2. The N=N bond distances in both compounds (Table 2) are in agreement with the corresponding values of similar compounds [24][25][26][27][28][29] and reflect their double bond character. The bond lengths of pairs of formally single C-N bonds at opposite sides around azo bridges are not sensitive to substituent effects and thus, they are almost equal in both compounds ( Table 2) single C-N bonds at opposite sides around azo bridges in both compounds are slightly different from each other due to a possible through-resonance effect between the electron-donating O atom and the two-electron accepting N atom.…”

Section: Resultssupporting

confidence: 84%

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: Resultssupporting

confidence: 84%

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

et al. 2009

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“…Some selected geometrical parameters experimentally obtained and theoretically calculated are listed in Table 2. The N=N bond distances are in agreement with the corresponding values of similar compounds [22][23][24]. In Residue 2, nitrogen atoms have the site occupancy factor of 0.539(6) in major and 0.461(6) in minor component.…”

Section: Structure Determinationsupporting

confidence: 85%

“…In Residue 2, nitrogen atoms have the site occupancy factor of 0.539(6) in major and 0.461(6) in minor component. While pairs of formally single C-N bonds at opposite sides around azo bridges in Residue 1 are comparable in their bond lengths, in Residue 2 they are slightly different from each other due to a possible through-resonance effect between the electron-donating O atom and the two-electron accepting N atom as is in similar compounds [22][23][24][25][26][27].…”

Section: Structure Determinationmentioning

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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“…In the next article, by Karabıyık et al [46], details of the trans stereochemistry of the (E)-3-methyl-4-(p-tolyldiazenyl)phenol compound were examined. The results suggest that hydrogen-bonding properties in the crystal lattice are fundamental in determining the crystallographically observed conformation of this compound.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Ponikvar

Liebman

2008

Struct Chem

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In this study, we relate the contents of the journal Structural Chemistry for the calendar year 2007 and thermochemistry. The year's articles were briefly summarized and a thermochemical comment written to supplement them. Frequently questions were asked and future research was suggested.Keywords Structural Chemistry Á Thermochemistry Á Thermodynamics Á Enthalpy of formation Á Enthalpy of phase change Á Enthalpy of reaction As practiced disciplines, structural chemistry and thermochemistry are very often unrelated. In this study, these disciplines are linked as relations are explicitly made using the contents of the journal Structural Chemistry (Vol. 18) for the calendar year 2007 as a scaffold for our analysis, for our selected articles in the discipline of structural chemistry. These studies have been reviewed by us, where we give them a thermochemical flavor. While this commentary is most generally written in terms of brief summaries of literature papers involving enthalpies of formation and/or reaction, not uncommonly we raise questions and even suggest possible future research. We are not, however, going to give a thermochemical slant on book reviews, honorary dedications, and obituaries although these works will be cited in our text.As such, this article is a sequel to our earlier related reviews of Structural Chemistry for the calendar years 2000 through 2004 [1-5]. Reviews for 2005 and 2006 are currently being prepared. Issue 1In the first article in the first issue of Structural Chemistry for 2007, Hargittai [6] asserted that while research is currently usually carried out in big groups, the most important ideas, observations and discoveries still belong to individuals who have to bring down dogmas or open entirely new areas in science. This may bring solace to the thermochemical community in which research groups are generally small, and the number of new practitioners sadly few.In the past decade, the crystal engineering of multidimensional arrays and networks containing metal ions has achieved considerable progress because of the increased interest in the potential utility of these compounds as zeolite-like materials [7-11], catalysts [12], or magnetic materials [13][14][15]. The thermochemistry of these species is complicated by their inherent complexity: however, estimation approaches of their key thermochemical quantities are increasingly reliable [16]. In the second article of this issue, by Wang et al. [17], the versatility of malonate dianion as a ligand for the construction of extended networks with different topologies dependent on the coordination geometry of the metal ion was discussed. The synthesis and structure of a novel malonate-bridged copper(II) compound in which copper(II) ions have two different coordination environments in a novel three-dimensional (3D) network was described. Metal malonates have been studied from a

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

Cited by 10 publications

References 26 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

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

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