Structures and vibrational spectra of pinacol.

Dahlqvist, Martti; Hotokka, Matti; Räsänen, Markku

doi:10.1016/s0301-0104(98)00041-x

Cited by 13 publications

(15 citation statements)

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“…Inspection of the crystal structure of 2g shows that the O–C–C–O units are gauche with dihedral angles of –68.0(2)° and –70.5(2)°, similar to the preferred tGg′ ground state of free pinacol derived by spectroscopy and QM. 24 For neopentyl glycol 1d , the preferred C 2 symmetric GG conformation of the chelating unit, 25 is maintained in the X-ray structures, as preferred in the free diols. Hence there is no evidence of additional strain caused by complexation in either 1,2-diol or 1,3-diol fluoride anion complexes.…”

Section: Resultsmentioning

confidence: 95%

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

et al. 2015

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Section: Resultsmentioning

confidence: 95%

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

et al. 2015

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“…Quantum‐mechanical studies on ethane‐1,2‐diol, 1 , documented elsewhere, go back about 40 years; those on the butane‐2,3‐diols, 2 and 3 , pinacol, 4 , and propane‐1,3‐diol, 5 , are rather more recent . Regardless of the functional and the basis set used, all methods indicate that gauche conformers predominate in 1,2‐diols.…”

Section: Resultsmentioning

confidence: 96%

Association of symmetrical alkane diols with pyridine: DFT/GIAO calculation of ¹H NMR chemical shifts

Lomas

Joubert

Maurel

2016

Magnetic Reson in Chemistry

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Proton nuclear magnetic resonance (NMR) shifts of the free diol and of its 1 : 1 and 1 : 2 hydrogen-bonded complexes with pyridine have been computed for five symmetrical alkane diols on the basis of density functional theory, by applying the gauge-including atomic orbital method to geometry-optimized conformers. For certain conformers, intramolecular OH···OH interactions, evidenced by high NMR OH proton shifts, are further enhanced on going from the free diol to the corresponding 1 : 1 diol/pyridine complex. This is confirmed by atoms-in-molecules and non-covalent interaction plots. The computed OH and CH proton shifts for the diol and the two complexes correlate well with values obtained by analysing data from the NMR titration of the diols in benzene against pyridine. Shift values for the diols in neat pyridine are calculated by weighting the shifts of the various protons in the three forms (free diol, 1 : 1 and 1 : 2 diol/pyridine complexes) according to the experimentally determined association constants. The results are in good agreement with those observed, and after empirical scaling, the root mean square difference is 0.18 ppm. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Quantum-mechanical calculations for the model systems ethane-1,2-diol (Yeh et al, 1994) and pinacol (2,2-dimethylbutane-2,3-diol; Dahlqvist et al, 1998) indicate that the best gauche conformer (OÐCÐCÐO 9 60 ) is ca. 8 kJ mol À1 lower in energy than the best trans conformer (OÐCÐCÐ O 9 180 ) because of the weak intramolecular OÐHÁ Á ÁO bond that is possible in the former.…”

Section: Gauche Conformers Predominatementioning

confidence: 99%

Crystal packing in vicinal diols C _n H_m(OH)₂

Brock

2002

Acta Crystallogr Sect B

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The O-HtriplebondO bonds in vic-diols C(n)H(m)(OH)(2) have been studied using data retrieved from the Cambridge Structural Database. About half of these diols form complete, or almost complete, sets of intermolecular O-HtriplebondO bonds (i.e. two satisfied donors per molecule). For this half of the structures the frequencies of high-symmetry space groups and of structures with Z' > 1 (more than one molecule in the asymmetric unit) are substantially elevated. The most common motif among fully bonded structures is an R(2)(2)(10) dimer, which can be linked in a variety of ways to form one-, two- or even three-dimensional patterns. Most of the other half of the vic-diols form simple O-HtriplebondO chains in which each OH group participates in only one intermolecular hydrogen bond. The space-group frequencies for this second group of structures are unexceptional. The most important factor determining the extent of O-HtriplebondO bond formation is the degree of substitution of the vic-diol. The spatial segregation of OH groups that is necessary for the formation of O-HtriplebondO bonds is found to make the dense filling of space more difficult because the intermolecular spacings that are appropriate for the O-HtriplebondO bonds may be inappropriate for the rest of the molecule.

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Structures and vibrational spectra of pinacol.

Cited by 13 publications

References 15 publications

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Association of symmetrical alkane diols with pyridine: DFT/GIAO calculation of ¹H NMR chemical shifts

Crystal packing in vicinal diols C _n H_m(OH)₂

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Structures and vibrational spectra of pinacol.

Cited by 13 publications

References 15 publications

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Association of symmetrical alkane diols with pyridine: DFT/GIAO calculation of 1H NMR chemical shifts

Crystal packing in vicinal diols C n H m (OH)2

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Association of symmetrical alkane diols with pyridine: DFT/GIAO calculation of ¹H NMR chemical shifts

Crystal packing in vicinal diols C _n H_m(OH)₂