Microwave spectral study of 2-fluorophenol: cis conformer

Dutta, A; Jaman, A.I.; Nandi, Rana

doi:10.1016/0022-2852(85)90224-3

Cited by 23 publications

(16 citation statements)

References 16 publications

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“…If we weight these values appropriately then the most likely values of E trans À E cis for the vapour are 1.0, 3.0, 2.6, 2.6 kcal mol À1 for the 2-fluoro, 2-chloro, 2-bromo and 2-iodo, respectively. The value for the 2-fluoro is the most uncertain as the microwave 32 and electron diffraction 33 experiments only suggested the existence of a second (trans) conformer without any measurements. It is however clear from the data in Table 5 that the theoretical calculations give much larger values of the conformer energies than the experimental values in every case.…”

Section: Discussionmentioning

confidence: 99%

“…A microwave study by Dutta et al 32 observed only transitions due to the cis conformer in 2-fluorophenol but noted that due to the poor signal to noise there could be up to 20% of the trans form. Also Vajda and Hargittai 33 in an electron diffraction study stated ''a second form of 2-fluorophenol not allowing an OHÁ Á ÁF interaction seems to be present in the vapour''.…”

Section: Microwave Spectroscopy/electron Diffractionmentioning

confidence: 99%

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Is there an intramolecular hydrogen bond in 2-halophenols? A theoretical and spectroscopic investigation

Abraham

Aliev

et al. 2015

Phys. Chem. Chem. Phys.

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The Abraham solute hydrogen bond acidity parameter A can be derived both from physical methods, A(Gen) and NMR experiments, A(NMR) and results for a large number of hydroxylic solutes show that the two methods agreed very well. However for halophenols the values of A(NMR) were not consistent with the A(Gen) values. The values of A(NMR) suggest that there is no intra-molecular hydrogen bonding in any of the 2-halophenols. In contrast the values of A(Gen) indicate that there is no intra-molecular hydrogen bonding in 2-fluorophenol, but weak intra-molecular hydrogen bonding in 2-chloro, 2-bromo, and 2-iodo-phenol. In view of this uncertainty in the presence or absence of intra-molecular H-bonds in the 2-halophenols, a detailed investigation of the methods used in the literature is presented together with a novel NMR method to determine the ratio of cis and trans forms in these compounds. The experimental data is complemented by a detailed theoretical analysis of the structures and bonding in these molecules to assess the presence or absence of an intra-molecular H-bond. We conclude that there is weak hydrogen bonding in 2-chloro, 2-bromo and 2-iodophenol but very little in 2-fluorophenol.

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Section: Discussionmentioning

confidence: 99%

Section: Microwave Spectroscopy/electron Diffractionmentioning

confidence: 99%

Is there an intramolecular hydrogen bond in 2-halophenols? A theoretical and spectroscopic investigation

Abraham

Aliev

et al. 2015

Phys. Chem. Chem. Phys.

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“…By improving the fits of both spectra all rotational lines could eventually be assigned with the result that the rotational constants for the ground state were, within their errors, identical to the ground state rotational constants of the cis isomer, as determined by microwave spectroscopy. 15 In the next step we performed new fits of our data, fixing the ground state rotational constants to the microwave data of the cis isomer. This yielded more accurate constants for the excited state.…”

Section: B High Resolution Measurementsmentioning

confidence: 99%

“…14 The microwave spectra of o-fluorophenol and its deuterated derivative only show the presence of the cis isomer. 15 However, the authors did not rule out the existence of a trans isomer, since the lines due to the trans form could be weaker than the detection limit.…”

Section: Introductionmentioning

confidence: 99%

Structural information on the S and S1 state of o-fluorophenol by hole burning and high resolution ultraviolet spectroscopy

Remmers

Meerts

Zehnacker‐Rentien

et al. 2000

The Journal of Chemical Physics

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The electronic transitions of o-fluorophenol situated at 36 799.382 cm Ϫ1 and 36 906.710 cm Ϫ1 , denoted the A and B bands, respectively, have been investigated by high resolution fluorescence excitation spectroscopy. Hole burning studies together with the high resolution spectroscopy results show that both bands originate in the same ground state and can be fitted to the rotational constants of the cis isomer. The rotational constants for the excited states are found to be AЈϭ3231.795 MHz, BЈϭ2207.92 MHz and CЈϭ1313.97 MHz for the A band and AЈϭ3226.945 MHz, BЈϭ2211.24 MHz and CЈϭ1321.03 MHz for the B band. The planarity of the ground state is lost upon electronic excitation, which enhances the activity of an out-of-plane vibration. The A and B band transitions arise from excitations to respectively the zero and first overtone levels in the double-minimum potential of this out-of-plane vibration, which shows similarities to the so-called butterfly mode observed in other benzene derivatives.

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“…Particularly the ortho halophenols have been the subject of numerous experimental [10][11][12][13][14][15][16][17] and theoretical [10,[18][19][20] studies focused on the bond strength, geometry, and stabilization energy induced by hydrogen bonding. Considering 2-bromophenol it has been shown in previous works that its molecular structure is planar, and the most stable conformation is that where the hydroxyl group adopts a cis configuration relatively to the bromine atom in 2-position, yielding the formation of a halogen-hydrogen bond.…”

Section: Introductionmentioning

confidence: 99%