Disordered Fluorine in 2-Fluorobiphenyl

Rajnikant,; Watkin, David J.; Tranter, George E.

doi:10.1107/s0108270195000631

Cited by 14 publications

(5 citation statements)

References 15 publications

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“…This large angle, due to intramolecular Br.-.Br and Br...H repulsive interactions, is only surpassed by 86.9(5) ° for decachlorobiphenyl (Pedersen, 1975) and 87.9" for 2,2',4,4',6,6'-hexachlorobiphenyl (Singh & McKinney, 1979). In comparison, the inter-ring angles for 2-fluorobiphenyl (Rajnikant et al, 1995(Rajnikant et al, ), 2,2'-dichlorobiphenyl (R0mming et al, 1974 and 2,2'-dibromooctafluorobiphenyl (Hamor & Hamor, 1980) are considerably smaller, measuring 54.1 (3), 66.5 and 76.0 (5) °, respectively. RCmming et al (1974) have previously compared inter-ring angles in 2,U-dihalobiphenyls observed in the gas phase with calculated values.…”

Section: (I)mentioning

confidence: 95%

2,2'-Dibromobiphenyl

MacNeil¹,

Decken²

1999

Acta Crystallogr C

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Section: (I)mentioning

confidence: 95%

2,2'-Dibromobiphenyl

MacNeil¹,

Decken²

1999

Acta Crystallogr C

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“…12 Furthermore, the presence of symmetry in the molecule has been shown to influence disorder in the fluorine position, for example, in 2-fluorobiphenyl, trans-4-fluoroazoxy-benzene and trans-4-fluoro-NNO-azoxybenzene. 13,14 The molecular assemblies in these structures have been shown to be stabilized by C-H/F hydrogen bonds. The question remains whether the intermolecular interactions are observed as a consequence of geometry alone.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the role of disordered organic fluorine in crystal packing: insights from halogen substituted benzanilides

et al. 2012

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The determination of the crystal and molecular structures of a large number of compounds containing the C(sp 2 )-F bond has been investigated in detail in halogenated benzanilides and also in liquids, namely the fluorinated amines. It has been observed that when the fluorine atom is present in the ortho or meta position with respect to the amide functionality in benzanilides or the amino group in fluorinated amines which are liquids at room temperature, the fluorine atom exhibits positional disorder. This is associated with changes in patterns of intermolecular interactions which affect crystal packing. Furthermore, the presence of a fluorine atom on the benzanilide framework, in the presence of a heavier halogen (chloro, bromo and iodo), meta or ortho to the amide group does not eliminate the disorder associated with these molecules. In this article, we highlight the salient features present in halogenated compounds exhibiting disorder in the position of organic fluorine with concomitant changes in crystal packing. This feature is also compared with related compounds exhibiting similarity in electronic features, namely positional disorder.

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“…The corresponding values are quite similar to that of � 44.4(1.2)°determined for the biphenyl molecule in gasphase. [25] For fluorobiphenyl, it has been determined as � 54.1°i n condensed phases using X-ray techniques [26] and � 49(5)°by gas-phase electron diffraction. [27] The balance of forces yielding almost the same torsional angle between the phenyl planes in FB, biphenyl, and o-fluorobiphenyl involves the π-conjugation between the two rings favouring a co-planar configuration and the steric repulsion between the adjacent atoms in orthoposition.…”

Section: Resultsmentioning

confidence: 99%

The Role of the Transient Atropisomerism and Chirality of Flurbiprofen Unveiled by Laser‐Ablation Rotational Spectroscopy

Verde

López

Blanco

2023

Chemistry A European J

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The combination of atropisomerism and chirality in flurbiprofen is shown to be relevant concerning its pharmacological activity. The two most stable conformers of a total of eight theoretically predicted for each R-or S-flurbiprofen enantiomers have been isolated in the cooling conditions of a supersonic jet and structurally characterized by laser ablation Fourier transform microwave spectroscopy. The detected conformers, whose structure is mainly defined by three dihedral angles, only differ in the sign of the phenyl torsion angle giving rise to S a and R a atropisomers. A comparison with the structures available for the R-and S-enantiomers complexed to COX isoforms reveals that the enzymes select only the S a atropisomers, resulting in a diastereoisomerspecific recognition. The most stable gas phase conformer is exclusively selected when using the S-enantiomer while the second is recognized only for the R-enantiomer. These experimental results highlight the importance of atropisomerism in drug design.

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Disordered Fluorine in 2-Fluorobiphenyl

Cited by 14 publications

References 15 publications

2,2'-Dibromobiphenyl

2,2'-Dibromobiphenyl

Evaluation of the role of disordered organic fluorine in crystal packing: insights from halogen substituted benzanilides

The Role of the Transient Atropisomerism and Chirality of Flurbiprofen Unveiled by Laser‐Ablation Rotational Spectroscopy

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