Crystal structure of Schiff base derivative of 2,2′-dihydroxybiphenyl-3-carbaldehyde with n-butylamine

Wojciechowski, Grzegorz; Ratajczak–Sitarz, Małgorzata; Katrusiak, Andrzej; Schilf, Wojciech; Przybylski, Piotr; Brzeziński, Bogumił

doi:10.1016/s0022-2860(03)00159-5

Cited by 43 publications

(17 citation statements)

References 38 publications

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“…145.58. The lengths of the comparable types of hydrogen bonds in the X-ray structures noted in literature are in the range of 2.48-2.68 Å and the angles vary from 1288 to 1618 32,[58][59][60]. The values calculated in this study are in these ranges.…”

supporting

confidence: 51%

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations

et al. 2006

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A new derivative of racemic gossypol with 2-thiophenecarbohydrazide (GHHT) and its complexes with monovalent cations have been synthesized and studied by electrospray ionization-mass spectroscopy (ESI-MS), multinuclear nuclear magnetic resonance (NMR), as well as by the Parametric Method 5 (PM5) methods. It is demonstrated that GHHT forms stable complexes of 1:1 stoichiometry with monovalent metal cations. The structures of the complexes are stabilized by three types of intramolecular hydrogen bonds. The spectroscopic methods have provided clear evidence that GHHT and its complexes exist in the DMSO-d6 solution in the N-imine-N-imine tautomeric forms. The structures of the GHHT and its complexes with Li+, Na+, K+, Rb+, and Cs+ cations are visualized and discussed in detail.

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confidence: 51%

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations

et al. 2006

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“…Zwitterionic forms are easily distinguishable from the other NH forms, since N ? -H bonds are longer than the standard interatomic separations observed in neutral N-H bonds (0.87 Å ) [9,[11][12][13]. The other ionic bonds in the zwitterions, C-O -and C=N ?…”

Section: Introductionmentioning

confidence: 83%

“…Except for these, another structural form known as the zwitterion is also observed [9,10]. Zwitterionic forms of o-hydroxy Schiff bases are regarded as a variant of their NH forms (Scheme 1), retaining the phenyl ring aromaticity and containing the protonated nitrogen atom.…”

Section: Introductionmentioning

confidence: 99%

The proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol

et al. 2010

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The crystal and molecular structures of an o-hydroxy Schiff base derivative, (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol, have been determined by single crystal X-ray diffraction analyses at 296 and 100 K. The results from temperature-dependent structural analysis regarding the tautomeric equilibrium of the compound were interpreted with the aid of quantum chemical calculations. To clarify the tautomerization process and its effects on the molecular geometry, the gasphase geometry optimizations of two possible tautomers of the title molecule, its OH and NH form, were achieved using DFT calculations with B3LYP method by means of 6-31 ? G(d,p) basis set. In order to describe the potential barrier belonging to the phenolic proton transfer, nonadiabatic Potential Energy Surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, O-H bond distance. The Harmonic Oscillator Model of Aromaticity (HOMA) indices were calculated in every step of the scan process so as to express the deformation in the aromaticities of principal molecular moieties of the compound. The results show that there is a dynamic equilibrium between the aromaticity level of phenol and chelate ring and furthermore p-electron coupling affecting overall molecule of the title compound. Charge transfer from phenol ring to pseudo-aromatic chelate ring increases with increasing temperature, whereas p-electron transfer from chelate ring to anisole ring is decreased as temperature increases. The most strength intramolecular H-bonds are observed for conformers close to transition state.

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“…The cis-quinoid and zwitterionic forms are not just resonance structures of each other, they can also exist separately. The zwitterionics can differ from cis-quinoid NH forms with their ionic N + -H bond distances and aromaticity of the rings [26][27][28]. The tautomeric forms and observed strong intramolecular hydrogen bonds depending on these forms can be seen in Fig.…”

Section: Introductionmentioning

confidence: 93%

Molecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study

Koşar

Albayrak

Odabaşoğlu

et al. 2011

Journal of Molecular Structure

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Crystal structure of Schiff base derivative of 2,2′-dihydroxybiphenyl-3-carbaldehyde with n-butylamine

Cited by 43 publications

References 38 publications

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations

The proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol

Molecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study

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Crystal structure of Schiff base derivative of 2,2′-dihydroxybiphenyl-3-carbaldehyde with n-butylamine

Cited by 43 publications

References 38 publications

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI+, Na+, K+, RB+, and Cs+ cations

The proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol

Molecular structure of (Z)-6-[(5-chloro-2-hydroxyphenylamino) methylene]-3-(diethylamino)cyclohexa-2,4-dienone: A combined experimental and theoretical study

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Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations

Multinuclear magnetic resonance, electrospray ionization–mass spectroscopy, and parametric method 5 studies of a new derivative of gossypol with 2‐thiophenecarbohydrazide as well as its complexes with LI⁺, Na⁺, K⁺, RB⁺, and Cs⁺ cations